DIKTAT MATA KULIAH

KIMIA ORGANIK

Disusun oleh

: Drs. Adiwarna

JURUSAN TEKNIK KIMIA FAKULTAS TEKNIK UNIVERSITAS MUHAMMADIYAH JAKARTA 2008
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DAFTAR ISI TINJUAN MATAKULIAH MODUL 1 : TEORI DASAR TENTANG ATOM DAN IKATAN ATOM Latihan Rangkuman Tes formatif : JENIS-JENIS IKATAN KIMIA Latihan Rangkuman Tes formatif : KONSEP DASAR SENYAWA ORGANIK Latihan Rangkuman Tes formatif MODUL 4 |: JENIS-JENIS REAKSI DALAM SENYAWA ORGANIK Latihan Rangkuman Tes formatif : JENIS-JENIS SENYAWA ORGANIK Latihan Rangkuman Tes formatif MODUL 6 : TEORI TENTANG STEREO KIMIA Latihan Rangkuman Tes formatif : PUSAT CHIRAL Latihan Rangkuman Tes formatif MODUL 8 : KARBOHIDRAT Latihan Rangkuman Tes formatif : ASAM AMINO DAN PROTEIN Latihan Rangkuman Tes formatif

MODUL 2

MODUL 3

MODUL 5

MODUL 7

MODUL 9

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MODUL 10

: TRIGLISERIDA Latihan Rangkuman Tes formatif : ALKALOID Latihan Rangkuman Tes formatif : TERPENOID Latihan Rangkuman Tes formatif : STEROID DAN SAPONIN Latihan Rangkuman Tes formatif : ASAM NUKLEAT Latihan Rangkuman Tes formatif : FLAVONOID DAN QUINONOID Latihan Rangkuman Tes formatif : POLIMER Latihan Rangkuman Tes formatif

MODUL 11

MODUL 12

MODUL 13

MODUL 14

MODUL 15

MODUL 16

KUNCI JAWABAN TES FORMATIF DAFTAR PUSTAKA KAMUS UMUM

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6. dan bisa mengidentifikasi dengan reagen khusus. Mata kuliah kimia organik meerupakan matakuliah wajib bagi mahasiswa yang mengikuti program S1 Teknik Kimia Fakultas Teknik Universitas Muhammadiyah jakarta. : Konsep dasar senyawa organik. Mengetahui bermacam-macam struktur senyawa karbohidrat. 5. Mengetahui struktur ester trigliserida. Mengenal susunan struktur asam nukleat. Mengenal tentang isomer. Mengetahui konsep dasar tentang atom dan molekul serta proses terjadinya ikatan kimia. 4. bermacam-macam reaksi organik. kiralitas berbagai senyawa organik serta bisa menentukan sifat optis aktisnnya.. Bisa membedakan senyawa organik dengan senyawa anorganik. dan bisa menistesa. quinonoid. sifat keasaman dan kebasaan menurut bronsted Lowry dan Lewis. : Trigliserida : Alkaloid : Terpenoid : Steroid dan saponin : Asam nukleat : Flavonoid dan quinonoid : Polimer 4 . Setelah mengikuti matakkuliah ini mahasiswa diharapkan mampu : 1. Mengetahui sifat-sifat kimia akibat terjadinya ikatan kimia dan gugus fungsi pada senyawa organik. muatan formal. flavonoid. : Teori tentang stereo kimia : Pusat chiral : Karbohidrat : Asam amino dan protein. 7. permberian nama senyawa organik. alkaloid. pembentukan ikatan peptida menjadi protein. momen dipol. 8. Matakuliah kimia organik ini mempunyai bobot 3 sks dengan kode KIM008 terdiri dari 16 modul Sebagai berikut : MODUL 1 MODUL 2 MODUL 3 MODUL 4 MODUL 5 MODUL 6 MODUL 7 MODUL 8 MODUL 9 MODUL 10 MODUL 11 MODUL 12 MODUL 13 MODUL 14 MODUL 15 MODUL 16 : Teori dasar tentang atom dan ikatan atom. 9. memberi nama. 2. bisa membedakan kelompok trigliserida. 10. Mengetahui jenis-jenis struktur asam amino. Mengetahui struktur dan pemberian nama bermacam-macam senyawa organik dan sintesanya. steroid. 3. bisa memberi nama. serta bisa mensintesa asam amino dan protein. Menngenal struktur dan nama beberapa jenis-jenis polimer serta bisa mensintesanya. : Jenis-jenis ikatan kimia. Setelah mengetahui dasar-dasar pembentukan ikatan mahasiswa harus tahu tentang berbagai gugus fungsi pada senyawa organik. struktur senyawa organik. saponin. Diharapkan setelah mengikuti matakuliah ini mahasiswa dapat memahami tentang konfigurasi elektron dalam atom dan molekul. dan mengenal biosintesa asam-asam lemak. Mengenal struktur dan bisa memeberi nama senyawa bahan alam yakni terpenoid. : Jenis-jenis reaksi dalam senyawa organik : Jenis-jenis senyawa organik.TINJAUAN MATAKULIAH Mata kuliah kimia organik merupakan matakuliah MKDU yang diajarkan pada semester II. sehingga dengan demikian mengetahui sifat keelektronegatifan. dan bisa mensintesanya. 11. proses terjadinya ikatan kimia. dan kelompok sennyawa organik.

Tingkat energi tertinggi 5f 6p 6s 4d 5s 4p 3d 4s 3p 3s 2p 2s 1s Tingkat energi terendah Orbital s maksimum terisi 2 elektron. 3d. 3p. 5s.MODUL I I. 2s. 3s. dan orbital f berbentuk sangat lonjung yang tersusun dalam 7 dimensi Ttingkat energi Orbital s Orbital p Orbital d Orbital d Orbital f Contoh orbital s adalah atom hindrogen yang mempunyai 1 elektron ( biru ) dan 1 proton (merah). 4d. orbital f maksimum terisi maksimum 14 elektron. Orbital s berbentuk lingkaran. TEORI DASAR TENTANG ATOM DAN IKATAN ATOM Konfigurasi Elektron dalam Atom Menurut Mendelejev electron dalam suatu atom akan mengisi orbital mulai dari tingkat energi terendah terlebih dahulu dari orbital 1s. 4s. 4p. orbital p berbentuk ellip yang tersusun dalam tiga dimensi. 2p. orbital d berbentuk ellip yang lebih lonjong yang tersusun dalam lima dimensi. orbital p maksimum terisi maksimum 6 elektron. orbital d maksimum terisi 10 elektron. 5 .

Contoh 1. (prinsip ekslusi Pauli). Pengisian electron pada orbital bertingkat energi sama harus terisi satu-satu electron terlebih dahulu ( Aturan Hund). Ada tiga prinsip yang harus dipenuhi dalam pengisian electron pada suatu orbital atom : 1. jika kedua electron tidak berpasangan dari dua atom berasal dari orbital s maka akan terbewntuk hibrid orbital s-s. jika dua electron tidak berpasangan dari dua atom berasal dari orbital p dan d maka akan terbewntuk huibrid orbital p-d. 3. Orbital molekul C2 s s Hibrida molekul Bila dua electron dari dua atom bergabung membentuk ikatan maka akan terbentuk hibrida orbital. Bentuk hibrid orbital tergantung kepada asal orbital electron pembentuk ikatan. jika electron tidak berpasangan dari dua atom berasal dari orbital 3s dan 3p maka akan terbewntuk huibrid 6 .Konfigurasi elektron dalam molekul Susunan tingkat energi dasar dalam suatu atom dapat dijelaskan dengan teori orbital atom dan tingkat energinya.( prinsip Aufbau) 2. jika dua electron tidak berpasangan dari dua atom berasal dari orbital s dan d maka akan terbewntuk huibrid orbital s-d jika dua electron tidak berpasangan dari dua atom berasal dari orbital s dan f maka akan terbewntuk huibrid orbital s-f. Electron mengisi orbital tingkat energi terendah terlebih dahulu. Hanya maksimum dua electron menempati suatu orbital dengan spin yang berlawanan arah. jika dua electron tidak berpasangan dari dua atom berasal dari orbital s dan p maka akan terbewntuk hibrid orbital s-p. orbital molekul H2 1s H 1s H H2 2p 2p 2p 2p s s s s C s C s C2 σ∗ σ σ∗ σ π∗ π Contoh 2. jika dua electron tidak berpasangan dari dua atom berasal dari orbital p dan f maka akan terbewntuk huibrid orbital p-f jika dua electron tidak berpasangan dari dua atom berasal dari orbital d dan f maka akan terbewntuk huibrid orbital d-f jika dua electron tidak berpasangan dari dua atom berasal dari orbital d dan d maka akan terbewntuk huibrid orbital d-d jika dua electron tidak berpasangan dari dua atom berasal dari orbital f dan f maka akan terbewntuk huibrid orbital f-f. Orbital molekul Bila dua atau lebih atom bergabung membentuk molekul unsur atau senyawa maka orbital electron molekul adalah merupakan gabungan dari orbital electron atom-atom penyusun molekul tersebut.

JENIS-JENIS IKATAN KIMIA Teori tentang ikatan kimia Ikatan kimia antar atom-atom bisa terjadi apabila electron kulit terluar dari suatu atom ada yang tidak berpasangan. Contohnya CH4.orbital sp3. jika electron tidak berpasangan dari dua atom berasal dari orbital 2s dan 2p maka akan terbewntuk huibrid orbital sp2. namun karbon sendiri bisa mengalami eksitasi dari keadaan dasar. 2p 2p H s s C s H H H s 2p σ∗ s s σ σ∗ π π∗ σ CH4 Sebelum membentuk molekul CH4 pada mulanya jika ikatan terjadi antara atom karbon dalam keadaan dasar dengan atom hindrogen hanya akan terbentuk molekul CH2. MODUL II II. Suatu atom bisa berikatan dengan beberapa atom lain jika atom tersebut mempunyai banyak elekton terluar (valensi) tak berpasangan. 2p 2p + H s s C s CH2 H 2p s s s σ∗ σ σ∗ σ π∗ π 2p 7 π∗ .

Hal ini terjadi pada molekul yang terdiri dari atom-atom elektropositif dan atom elektronegatif membentuk molekul polar. Molekul polar apabila dilarutkan dalam pelarut polar maka jarak atom elektropositif dan elektronegatif menjadi lebih jauh.2p 2p H H 1s + 1s 1s 1s 4H 2p 2s 2s 1s 1s CH4 σ∗ σ σ∗ σ π 2s 1s C Ground state 2s 1s C Exited state Jenis-jenis ikatan kimia Ikatan ion Ikatan ion terjadi dalam suatu molekul jika molekul tersebut mengalami polarisasi muatan elektrostatik.atom oksigen mempunyai 9 elektron sehingga bermuatan (-). Ikatan kovalen Ikatan kovalen adalah pemasangan electron tunggal dua atom atau lebih membentuk molekul tanpa terjadinya polarisasi electron. Senyawa organic kebannyakan tidak ada yang berikatan polar tetapi hanya berikatan semi polar. sehingga dengan demikian akan terjadi polarisasi muatan elektrostatik. Ikatan hydrogen dikenal dari sifat air yang mempunyai titik didih lebih tinggi dari molekul lain seperti H2S dan CH4. Kedua electron yang berpasangan dari dua atom berotasi mengitari inti dari masing-masing atom penyusunnya. C. Ikatan hydrogen terjadi apabila electron dari atom hydrogen dalam suatu molekul beredarar pada orbit electron atom. Contohnya molekul CH4. air dengan berat molekul 18 mempunyai titik didih 100 oC sedangkan H2S dengan 8 . H C H H Ikatan hydrogen Ikatan hydrogen adalah ikatan atom hydrogen dalam molekul senyawa asam Lewis dengan atom-atom elektronegatif dalam dasa Lewis. pada molekul Na(H2O)2+ Elektron atom Natrium hanya 10 elektron yang mengitari orbit inti atom Natrium sehingga atom natrium kekurangan 1 elektron sehingga menjadi bermuatan (+) sedangkan atom oksigen yang mempunyai 8 elektron pada molekul OH. + 4 H. : H . sebaliknya atom elektronegatif akan menarik satu electron at6om elektropositif yang beredar pada inti atom elektronegatif sehingga terbentuklah muatan negative akibat atom elektronegatif kelebihan electron seperti reaksi berikut : 11 Na8OH + H2O 10 Na(H2O)2+ + 9OH- Atom Natrium yang mempunyai 11 elektron dan 11 proton. dimana electron terkuar dari atom elektro positif beredar pada inti atom elektronegatif sehingga atom elektropoasitif akan kekurangan electron dan kelebihan proton keadaan seperti ini membentuk mnuatan positif.

d-f. dan sp ada pada senyawa alkuna. Sp3 ada pada senyawa alkana. 2p π∗ 2p 2p H H 1s + 1s 9 2p 2s σ∗ π . Hibrida molekul terjadi dari penggabungan electron tak berpasangan pada orbital dalam suatu molekul dari atom-atom penyusunnya. sp2. p-f. p-d. s-p. Bentuk hibrida molekul pada senyawa organic adalah sp3. s-d.berat molekul 34 mempunyai titik didih 25 oC dan C2H6 dengan berat molekul 30 mempunyai titik didih 25 oC -5 C ikatan vanderwalls London force Bentuk-bentuk hibrida molekul Hibridisasi adalah penggabungan electron yang tidak berpasangan dalam orbital suatu atom dengan electron yang tak berpasangan dari atom lain. 2p π∗ 2p 2p H 2s 1s C Ground state 2s 1s C Exited state H 1s + 1s 1s 1s 4H 2p 2s 2s 1s 1s CH4 σ∗ σ σ∗ σ π Hibridisasi sp2 pada molekul alkena berarti 1 dari 3 elektron orbital S hydrogen masuk ke orbital 2S dan 3 elektron orbital S dari hydrogen masuk ke 3 orbital P dari atom karbon. dan sp. sp2 ada pada senyawa alkena. p-p. atau f-f tergantung kepada asal orbital electron dari masing-masing atom. d-d. s-f. Orbital yang terbentuk dari hibridisasi ini disebut hybrid orbital. 2p π∗ 2p 2p H 2s 1s 2s 1s H 1s + 1s 1s 1s 4H 2p 2s 2s 1s σ∗ σ σ∗ π C C 1s σ Ground state Exited state -CH3 Hibridisasi sp3 pada molekul alkana berarti 1 dari 4 elektron orbital S hydrogen masuk ke orbital 2S dan 3 elektron orbital S dari hydrogen masuk ke 3 orbital P dari atom karbon. Hybrida orbital bisa berbentuk s-s. Hibridisasi sp3 pada molekul alkana berarti 1 dari 4 elektron orbital S hydrogen masuk ke orbital 2S dan 3 elektron orbital S dari hydrogen masuk ke 3 orbital P atom karbon.

Elektron-elektron Dallam atom tidak berpasangan secara sama oleh kedua inti atom.5 dinyatakan sebagai unsur elektropositif.5 dinyatakan dinyatakan lebih elektronegatif sedangkan unsur yang mempunyai elektronegatifitas dibawah 2.0 Al 1.0 F 4 Unsur yang mempunyai elektronegatifitas diatas 2. Elektronegatifitas dari beberapa jenis unsur Unsur elektronegatifitas unsur elektronegatifitas H 2.3 Li 1. Sebaliknya ikatan pada Na-Cl adalah murni ionic dan terbentuk gaya tarik medan elektrostatik antara ion Natrium yang bermuatan positif dengan ion klorida yang bermuatan negative. akan tetapi diperkirakan ikatan yang terjadi merupakan kelanjutan dari kemungkinan antara ikatan kovalen sempurna dengan distribusi elektron yang simetris atau sebaliknya.0 F 4.6 Si 1.2 Mg 1. Belum ada penjelasan terperinci mengenai konsep ikatan kovalen polar.1 O 3. Sebagai contohhnya ikatan -C-C. Akan tetapi kebanyakan molekul senyawa organic adalah polar.6 N 3.0 I 2.2s 1s C Ground state 2s 1s C Exited state 1s 1s 4H 2s 1s 1s σ σ∗ -CH2 σ Polarisasi dan elektronegatifitas. oleh karena itu merupakan ikatan kovalen sempurna. -C :Cl . namun distribusi electron pada ikatan atom-atom tertentu adalah merupakan bentuk yang tidak simetris. dan ikatan ionic sempurna atau sebaliknnya. -C:C.6 Be 1.9 B 2. dua electron yang berikatan dipasangkan bersama antara kedua atom karbon yang setara.4 Br 3.0 P 2. Dari sekiian banyak molekul senyawa organic hanay sedikit sekalli yang ditemukan berupa senyawa dipolar.2 C 2. Sehinngga dengan demikian ikatan kimia pada atom-atom sangat ditentukan oleh kondisi atau situasi apakah yang terbentuk ikatan kovalen atau ionic. Perbedaan kepolaran atom-atom yang berikatan mengakibatkan terjadinnya elektronegatifitas. Hal ini menunjukan meskipun tidak bisa mengikuti muatan formal atom-atom. .5 S 2.6 Na 1. Tabel 1. k n o a S f i i δ− t δ+ i 10 .0 Cl 3. Na+:ClPada ikatan -C-Cl kemungkinan besar terjadi penarikan electron agak kuat oleh suatu atom dari pada atom lainnya.pada etana adalahh simetris.

Unsur-unsur yang berada pada sebelah kanan table atom berkala seperti oksigen. sehingga dalam penggambarannya electron tertarik kearah atom elektronegatif ini dari pada atom karbon.2 Cl-3. Anda mungkin bisa membuat tali bergetar dengan panjang gelombang lebih pendek dari yang mendasar. semakin besar energi potensial elektron memiliki. Keadaan semakin tinggi energi. Awan-awan elektron yang berlapislapis satu di dalam yang lain ke dalam satuan yang disebut kerang (berpikir boneka Rusia bersarang). Sebagai contoh molekul H3C-Cl berikut : H2. maka terbetuklah ikatan terpolarisasi.2 H2. Anda bisa membayangkan bahwa gelombang di tali adalah frekuensi fundamentalnya. Electron orbitals Elektron orbit atom dalam awan bentuk berbeda dan ukuran. (Pekerjaan oleh Albert Einstein dan lain-lain mengungkapkan bahwa pada kenyataannya. Anda mereka mungkin melihat bahwa tali memiliki lebih dari satu tempat sepanjang panjangnya mana bergetar dari titik tertinggi ke tempat terendah. cahaya dan materi semua berperilaku dengan sifat ganda. dan klorin adalah lebih elektronegatif dibandingkan dengan karbon. Poin yang tinggi dan rendah jatuh tepat di tengah. dan tempat di mana tali tidak bergerak banyak (node) terjadi hanya pada dua ujung.) Salah satu hasil dari penelitian ini adalah bahwa elektron tidak hanya di orbit sederhana sekitar inti seperti yang kita bayangkan bulan untuk mengelilingi bumi.5 H2. Unsur-unsur yang berada sebelah kiri table atom berkala adalah unsure-unsur elektropositif dari ppada karbon dan kurang kuat menarik electron. Anda akan melihat bahwa ada satu atau lebih tempat (atau node) sepanjang panjangnya mana tali 11 . seperti sebuah batu di puncak bukit memiliki lebih energi potensial dari sebuah batu di dasar sebuah lembah. terkecil paling dalam memiliki keadaan energi terendah dan elektron di kulit. Selanjutnya. dengan elektron menduduki shell. Atom karbon akan menjadi bermuatan parsil positif yang + dilambangkan dengan (δ ) dan atom elektronegatif akan menjadi bermuatan parsil negative − yang dilambangkan dengan (δ ).2-C2. sehinga jika atom karbon berikatan dengan atom diatas akan menarik electron lebih kuat kearahnya dari pada atom karbon. Jika Anda melompat jumprope. Ekor dari panah adalah atom yang kekurangan muatan electron dan kepala dari panah adalah atom yang kelebihan muatan electron.1 Arah pada tanda panah digunakan untuk menunjukkan arah kepolaran.Dari table diatas terlihat bahwa antara atom karbon dan hydrogen mempunyai elektronegatifitas hamper sama maka iakatan –C-H adalah ikatan non polar. terbesar terluar memiliki keadaan energi tertinggi. dan hal ini sangat jelas diamati pada partikel terkecil. Konsep-konsep ini akan menjadi penting dalam memahami konsep-konsep kemudian seperti aktivitas optik senyawa kiral serta banyak hal menarik di luar bidang kimia organik (seperti bagaimana laser bekerja). melainkan menempati ruang seolah-olah mereka gelombang pada permukaan bola. menggunakan lebih banyak energi daripada Anda hanya akan lompat tali. Jika Anda menjabat tali cukup cepat dengan cara rythmic. Sehingga bila atom karbon berikatan dengan salah satu atom ini. Berdasarkan konvensi kimia electron bergerah menuju arah panah. florin. Wave nature of electrons Elektron berperilaku sebagai partikel tapi juga sebagai gelombang.

or modes the strings can vibrate. 12 . P orbital The next lowest-energy orbital is the p orbital. Electrons in this orbital are in their fundamental frequency. for that matter. Extending this now into three dimensions. and f. The algebraic expressions he developed. and pz. As one progresses up through the shells (represented by the principle quantum number n) more types of orbitals become possible. There are three p-orbitals each oriented along one of the 3-dimensional coordinates x. y or z. Electron shells Each different shell is subdivided into one or more orbitals. py. Many organic chemists need never actually work with these equations. p. S orbital The s orbital is the orbital lowest in energy and is spherical in shape. we can recognize that a drum makes sound by vibrations that occur across the 2-dimensional surface of the drumhead. the s orbital has the longest wavelength allowed for an electron orbiting a nucleus and this orbital is observed to have the lowest energy. which also have different energy levels. and the patterns or modes of vibration are referred to as spherical harmonics. The sound made by these instruments comes from the different ways. d. These three different p orbitals can be referred to as the px. Its shape is often described as like that of a dumbbell. we think of the electron as vibrating across a 3-dimensional sphere.Or consider stringed musical instruments. and are named by a letter. We can refer to these different patterns or modes of vibrations as linear harmonics. a drumhead). but it helps to understand where the pictures we use to think about the shapes of these orbitals come from. known as Legendre polynomials. Longer wavelengths have less energy. They are: s. Each shell in an orbital has a characteristic shape. The mathematical analysis of spherical harmonics were worked out by the French mathematician Legendre long before anyone started to think about the shapes of electron orbitals. describe the three dimension shapes of electron orbitals in much the same way that the expression x2+y2 = z describes a circle (or. although the energy difference between orbitals is less than the energy difference between shells. Going from there.

dxz. 3. Pengisian electron pada orbital bertingkat energi sama harus terisi satu- satu electron terlebih dahulu ( Aturan Hund). Orbital molekul 13 . Ada tiga prinsip yang harus dipenuhi dalam pengisian electron pada suatu orbital atom : 1. or z axes. Three of them are roughly X-shaped. Konfigurasi elektron dalam molekul Susunan tingkat energi dasar dalam suatu atom dapat dijelaskan dengan teori orbital atom dan tingkat energinya. these three d orbitals have a node at the origin of the coordinate system where the three axes all come together. Hanya maksimum dua electron menempati suatu orbital dengan spin yang berlawanan arah. for instance. although electrons in these orbitals rarely come into play in organometallic reactions involving these elements. F orbitals are filled in the elements of the lanthanide and actinide series. however. Like the p-orbitals. and dyz. these three d orbitals are not oriented along the x. and might be viewed as being shaped like a crossed pair of dumbbells .The s and p orbitals are important for understanding most of organic chemistry as these are the orbitals that are occupied by the type of atoms that are most common in organic compounds. lies in the xy plane. but we will not discuss their shapes here.( prinsip Aufbau) 2. but instead are oriented in between them. (prinsip ekslusi Pauli). F orbital and beyond There are 7 kinds of F orbitals. as shown here. D orbital There are 5 types of d orbitals. They are referred to as dxy. y. The dxy orbital. Electron mengisi orbital tingkat energi terendah terlebih dahulu. but the lobes of the orbital point out in between the x and y axes. Unlike the p orbitals.

Bentuk hibrid orbital tergantung kepada asal orbital electron pembentuk ikatan. Contoh 1. orbital molekul H2 1s H 1s H H2 Contoh 2. jika electron tidak berpasangan dari dua atom berasal dari orbital 2s dan 2p maka akan terbewntuk huibrid orbital sp2. jika dua electron tidak berpasangan dari dua atom berasal dari orbital s dan d maka akan terbewntuk huibrid orbital s-d jika dua electron tidak berpasangan dari dua atom berasal dari orbital s dan f maka akan terbewntuk huibrid orbital s-f. jika dua electron tidak berpasangan dari dua atom berasal dari orbital s dan p maka akan terbentuk hibrid orbital s-p. jika kedua electron tidak berpasangan dari dua atom berasal dari orbital s maka akan terbewntuk hibrid orbital s-s. jika electron tidak berpasangan dari dua atom berasal dari orbital 3s dan 3p maka akan terbewntuk huibrid orbital sp3.Bila dua atau lebih atom bergabung membentuk molekul unsur atau senyawa maka orbital electron molekul adalah merupakan gabungan dari orbital electron atom-atom penyusun molekul tersebut. jika dua electron tidak berpasangan dari dua atom berasal dari orbital p dan d maka akan terbewntuk huibrid orbital p-d. 14 . jika dua electron tidak berpasangan dari dua atom berasal dari orbital p dan f maka akan terbewntuk huibrid orbital p-f jika dua electron tidak berpasangan dari dua atom berasal dari orbital d dan f maka akan terbewntuk huibrid orbital d-f jika dua electron tidak berpasangan dari dua atom berasal dari orbital d dan d maka akan terbewntuk huibrid orbital d-d jika dua electron tidak berpasangan dari dua atom berasal dari orbital f dan f maka akan terbewntuk huibrid orbital f-f. Orbital molekul C2 2p 2p 2p 2p s s s s C s C s σ∗ σ σ∗ σ π∗ π s s C2 Hibrida molekul Bila dua electron dari dua atom bergabung membentuk ikatan maka akan terbentuk hibrida orbital.

Contohnya CH4. Suatu atom bisa berikatan dengan beberapa atom lain jika atom tersebut mempunyai banyak elekton terluar (valensi) tak berpasangan. 2p 2p + H 2s 1s C 1s CH2 2p 2p 2p H 2s 2s H 1s + 1s 1s 1s 15 2p 2s 2s 1s σ∗ σ σ∗ σ H 2p 2s 2s σ∗ σ π∗ π π∗ π .Teori tentang ikatan kimia Ikatan kimia antar atom-atom bisa terjadi apabila electron kulit terluar dari suatu atom ada yang tidak berpasangan. 2p 2p H s s C s CH4 H H H s 2p σ∗ s s σ σ∗ σ π π∗ Sebelum membentuk molekul CH4 pada mulanya jika ikatan terjadi antara atom karbon dalam keadaan dasar dengan atom hindrogen hanya akan terbentuk molekul CH2. namun karbon sendiri bisa mengalami eksitasi dari keadaan dasar.

1s C Ground state 1s C Exited state 4H 1s CH4 σ Jenis-jenis ikatan kimia Ikatan ion Ikatan ion terjadi dalam suatu molekul jika molekul tersebut mengalami polarisasi muatan elektrostatik. : H . dimana electron terkuar dari atom elektro positif beredar pada inti atom elektronegatif sehingga atom elektropoasitif akan kekurangan electron dan kelebihan proton keadaan seperti ini membentuk mnuatan positif.atom oksigen mempunyai 9 elektron sehingga bermuatan (-). sehingga dengan demikian akan terjadi polarisasi muatan elektrostatik. Kedua electron yang berpasangan dari dua atom berotasi mengitari inti dari masing-masing atom penyusunnya. + H. sebaliknya atom elektronegatif akan menarik satu electron at6om elektropositif yang beredar pada inti atom elektronegatif sehingga terbentuklah muatan negative akibat atom elektronegatif kelebihan electron seperti reaksi berikut : 11 Na8OH + H2O 10 Na(H2O)2+ + 9OH- Atom Natrium yang mempunyai 11 elektron dan 11 proton. 16 H C H H . Hal ini terjadi pada molekul yang terdiri dari atom-atom elektropositif dan atom elektronegatif membentuk molekul polar. C. Contohnya molekul CH4. Ikatan kovalen Ikatan kovalen adalah pemasangan electron tunggal dua atom atau lebih membentuk molekul tanpa terjadinya polarisasi electron. pada molekul Na(H2O)2+ Elektron atom Natrium hanya 10 elektron yang mengitari orbit inti atom Natrium sehingga atom natrium kekurangan 1 elektron sehingga menjadi bermuatan (+) sedangkan atom oksigen yang mempunyai 8 elektron pada molekul OH. Molekul polar apabila dilarutkan dalam pelarut polar maka jarak atom elektropositif dan elektronegatif menjadi lebih jauh. Senyawa organic kebannyakan tidak ada yang berikatan polar tetapi hanya berikatan semi polar.

. Kita bisa menggambarkan moment dipole dengan cara berikut. Ukuran besaran keseluruhan kepolaran dari masing ikatan dalam molekul ini disebut moment dipole. misalkan juga dalam molekul tersebut ada pusat grafitasi muatan negative. Pada cara ini nilai muatan formal dihitung berdasarkan jumlah electron kulit terluar dalam suatu atom dikurangi dengan jumlah electron kulit terluar dalam atom berikatan atau jumlah electron kulit terluar Jumlah electron Mf = kulit terluar dalam Atom bebas Jumlah electron Mf = kulit terluar dalam Atom bebas Momen dipole Bila masing-masing ikatan dalam suatu molekul polar memebentuk momen. Cara penentuan muatan elektrostatik secara teoritis dapat ditentukan dengan cara pendekatan muatan formal.8 x 10-10 esu d = jarak antar muatan listrik statis dalam sentimeter 17 . maka ikatan keseluruhan dalam molekul sering kali jadi polar. misalkan ada suatu pusat grafitasi ari seluruh muatan positif dalam suatu molekul. Kepolarann total ini bersal dari penjumlahan kepolaran semua ikatan dan kontribusi pasangan electron bebas dalam suatu molekul. Jika kedua pusat grafitasi muatan ini tak berimpitan maka molekul tersebut mempunyai muatan listrik yang tak simetris dan mempunyai muatan total. Moment dipole (µ ) didefinisikan sebagai besaran unit muatan listrik (e) dikali jarak (d) antar pusat muatan yang dinyatakan dalam satuan debye (D) – – jumlah electron kulit terluar dalam. atom berikatan ½ jumlah electron kulit terluar dalam atom berikatan jumlah elektron – kulit terluar bebas µ = ( e ) x ( d ) x ( 10 18 ) = Debye e = muatan listrik dalam satuan elektrostatik ( esu) = 4.Muatan Formal.

karena senyawa ini mempunyai muatan formal pada dua atomnya.50 3. Nilai moment dipole dari beberapa senyawa kimia senyawa Moment dipole NaCl CH3Cl H2O H3COH NH3 H4C CCl4 ( D) 9. sedangkan basa adalah suatu molekul menerima proton ( H+ ).8 x 10 -10 esu ) dipisahkan satu sama lainnya sejarak 1 Ao (10-8 cm) .00 0. sedangkan basa adalah suatu molekul yang mempunyai pasangan electron bebas yang bisa didonorkan orbital electron terluar yang kosong dari molekul lainnya.87 1. maka didapatkan nilai µ sebagai berikut : µ = ( 4.46 Dari table 1 diatas terlihat bahwa NaCl mempunyai nilai moment dipole yang luar biasa besarnnya karena senyawwa ini bersifat ion.00 0. 18 .sebagai contoh jika satu proton dan satu electron ( e = 4. Konsep dasar asam basa Pengertian asam secara kimia menurut konsep bronsted-Lowry adalah suatu molekul yang dapat melepaskan proton ( H+ ). Nitrometana H3CNO2 mempunyai nilai moment dipole cukup besar.70 1.00 Senyawa H3C-CH3 C6H6 BF3 H2C=N+ =NH3C-N+=O OMoment dipole (D) 0.8 D Secara percobaan akan relative lebih mudah mengukur moment dipole seperti nilainya tercantum dalam table berikut : Tabel 1.47 0.00 1. Keasaman adalah kemampuan suatu senyawa melepaskan proton dan kebasaan adalah kemampuan suatu senyawa untuk menerima proton. Menurut Lewis asam adalah senyawa yang mempunyai orbital electron terluar yang kosong untuk ditempati oleh pasangan electron bebas dari suatu molekul senyawa lain.00 1.8 x 10 -10 esu ) (10-8 cm ) (1018) = 4.85 1.00 0.

Gugus fungsi adalah merupakan bahagian dari molekul besar senyawa organic.MODUL III III.1-diol.2-diol. Ia tersusun dari atom atau gugus atom-atom yang menentukan karakteristik dari kereaktifan kimia senyawa. CH3CH(CH3)CH2NH(CH3) is N. Ada senyawa organic yang mempunyai mono gugus fungsi dan ada pula yang poli gugus fungsi. Jenis-jenis gugus fungsi senyawa organic yang telah diketahui Tabel 2. dll.). tri-. Awalan substituen dimulai berurutan seuai abjad. not fluorochloromethane. e. e. Pusat reaksi senyawa organic berada pada gugus fungsi tersebut.g.g. Priority Functional group Formula Prefix Suffix Gugus fungsi senyawa organic 1 Cations e. Jika suatu senyawa mempunyai banyak gugus fungsi disebut poli gugus fungsi. either prefixed or suffixed.2-dimethylpropanamine. If there are multiple functional groups of the same type. the position numbers are ordered numerically (thus ethane-1. not ethane-2. Ammonium –NH4+ -onioammonio- -onium -ammonium 2 Carboxylic acids Thiocarboxylic acids Selenocarboxylic acids Sulfonic acids Sulfinic acids Sulfenic acids –COOH –COSH –COSeH –SO3H –SO2H –SOH carboxythiocarboxyselenocarboxysulfosulfinosulfeno- -oic acid* -thioic acid* -selenoic acid* -sulfonic acid -sulfinic acid -sulfenic acid 3 Carboxylic acid derivatives Esters Acyl halides Amides Imides Amidines –COOR –COX –CONH2 –CON=C< –C(=NH)NH2 R-oxycarbonylhalidealcanoylcarbamoyl-imidoamidino- -R-oate -oyl halide* -amide* -imide* -amidine* 19 .) The N position indicator for amines and amides comes before "1". KONSEP DASAR SENYAWA ORGANIK Penggolongan senyawa organic didasarkan atas reaktifitas dari gugus yang terdapat dalam susunan molekul senyawa organic. (diluar jumlah substituen seperti di-.g. chlorofluoromethane. Jika suatu senyawa hanya mempunyai satu gugus fungsi maka senyawa itu disebut mono gugus fungsi.

are the most commonly used. Jenis-jenis gugus fungsi senyawa organic yang telah dikenal No Jenis senyawa 1 Alkana Gugus fungsi R-CH3 20 Contoh Akhiran nama senyawa -ana . in which the carbon atom is counted as part of the preceding chain. Tabel 3. See individual functional group articles for more details.4 Nitriles Isocyanides –CN –NC cyanoisocyano- -nitrile* isocyanide 5 Aldehydes Thioaldehydes –CHO –CHS formylthioformyl- -al* -thial* 6 Ketones Thioketones >CO >CS oxothiono- -one -thione 7 Alcohols Thiols Selenols Tellurols –OH –SH –SeH –TeH hydroxysulfanylselanyltellanyl- -ol -thiol -selenol -tellurol 8 Hydroperoxides –OOH hydroperoxy- -hydroperoxide 9 Amines Imines Hydrazines –NH2 =NH –NHNH2 aminoiminohydrazino- -amine -imine -hydrazine 10 Ethers Thioethers Selenoethers –O– –S– –Se– -oxy-thio-seleno- 11 Peroxides Disulfides –OO– –SS– -peroxy-disulfanyl- *Note: These suffixes.

2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 Alkena Alkuna Halide alkana Alkanol Alkoksi alkana Alkanal Alkanon Alkil alkanoat Alkanoat Alkanoil halide Alkanoil amida Alkil amina Alkil sianida Alkil nitrit Alkil sulfide Alkil Sulfoksi alkana Dialkil Sulfonat Alkil logam Alkanoailsulfat Alkanoail sianida Alkanoail halide Alkanoail amida Alkanoilsianida Alkil karbamat diAlkil disulfida Dialkil sulfida Dithiokarbonat Alkilsulfonat Alkil sulfinat Dialkilsulfat Alkil posfat Alkanoil posfit Alkanoail posfat C=C C C RX ROH ROR R-C=O H R-C=O R R-C=O OR R-C=O OH R-C=O X R-C=O NH2 RCH2NH2 RCH2-C N RCH2NO2 RCH2SH R-SO-R R-SO2-R RCH2M R-C=O OSO3H R-C=O OCN R-C=O OX R-C=O ONH2 R-C=O CN R-C=S SH R-S-S-R’ R-S-R RO-C=S SH O R-O-S-OH O R-O-S=O OH R-O-SO2-OR R-PO3H2 R-C=O OPO3H2 R-C=O 21 -ena -una -ol -oksi -ana -al -on -il -oat -oat -oil -ida -oil –amida -il -amina -il sianida -il nitrat -il sulfida -il sulfoksana -il -il logam -oail sulfat -oail sianida -oail halida -oail amida -oil sianidda -il karbamat -il disulfida -il sulfida -il thiokarbonat Il sulfonat -il sulfinat -il sulfat -il posfit -il posfat Posfo alakanoat .

Prop.35 Alkil posfat PO4H2 ROPO2H Table of Functional groups Alk is the prefix of the group (Meth. Eth.) IUPAC nomenclature for cyclic parent chains (if different from straight chains) Family Structur e IUPAC nomenclature Common nomenclature Alkyl groups R— Alkyl - Alkyl Halogens R— halogen Halo'alkane - Alkyl halide Alcohols R—OH Alkanol - Alkyl alcohol Amines R—NH2 Alkanamine - Alkyl amine Carboxylic acids (Alk + 1)anoic acid Cycloalkanecarboxylic acid - Aldehydes Alkanal Cycloalkanecarboxaldehyde - Ketones Alkanone - Alk(1)yl Alk(2)yl ketone Thiols R—SH Alkanethiol - - 22 . etc.

by comparing how other molecules containing the same types of parts are known to react. Functional groups are specific atoms. is an oxygen with a hydrogen attached. A functional group makes up part of a larger molecule. functional groups have characteristic chemistries. that allow us to predict how a compound we have never seen before may react. the writing will be in terms of functional groups. the hydroxy group that characterizes alcohols. Memorizing Functional Groups Don't deceive yourself and think that you can simply skim over the functional groups and move on. It will be assumed that the student is familiar with most of the ones in the tables below. An -OH group on one molecule will tend to react similarly. -OH. Organic reactions usually take place at the functional group. As you proceed through the text. so learning about the reactivities of functional groups will prepare you to understand many other things about organic chemistry. It's simply impossible 23 . It could be found on any number of different molecules.Amides (Alk + 1)anamide Cycloalkanecarboxamide - Ethers R1—O— R2 alkoxyalkane - Alk(1)yl Alk(2)yl ether Esters Alk(1)yl Alk(2)aneoate Alk(1)yl Cycloalk(2)anecarboxylate Alk(1)yl (Alk + 1)(2)anoate Alcohols Organic Chemistry/Overview of Functional Groups The number of known organic compounds is quite large. organic chemicals consist of a relatively few similar parts. Fortunately. about 7 million organic compounds in total. For example. to an -OH on another molecule. although perhaps not identically. combined in different ways. ions. Just as elements have distinctive properties. or groups of atoms having consistent properties. there are many times more organic compounds known than all the other (inorganic) compounds discovered so far. In fact. These parts of organic molecules are called functional groups. The identification of functional groups and the ability to predict reactivity based on functional group properties is one of the cornerstones of organic chemistry.

Aldehyde. Your initial set of cards should include. at the very least: Alkene. try going through your cards and looking at the names and then drawing their structure on a sheet of paper.to discuss chemistry without knowing the "lingo". Functional groups containing . But the above list will give you what you need to continue on. Alcohol. and Thiol. After you've learned all these. add a couple more cards and learn those. Again.. Carboxylic Acid. you're ready to move on. Ester. Amine. If you choose to move on without learning the "lingo". Get a pack of index cards and write the name of the functional group on one side.. Common functional groups include: Chemical class Graphical Formula Group Formula Prefix Suffix Example Acyl halide Haloformyl RCOX haloformyl- -oyl halide Acetyl chloride (Ethanoyl chloride) Alcohol Hydroxyl ROH hydroxy- -ol Methanol 24 . It's like trying to learn French without first learning the meaning of some of the words. And don't just memorize say. One of the easiest ways to learn functional groups is by making flash cards. Ketone. Once you have the minimal list above memorized backwards and forwards. Sulfide. But don't stop learning the groups. the names of the structures. For now. using the French analogy. it's like trying to ignore learning the vocabulary and then picking up a novel in French and expecting to be able to read it. a list of the most important ones you should know is provided here. and draw its chemical representation on the other. Alkyl halide (or Haloalkane). characterized by specific elemental composition and connectivity. Ether. then you're not going to understand the language of the chapters to come. Acyl Chloride (or Acid Chloride). that confer reactivity upon the molecule that contains them. To test yourself. Then add a few more and learn those. In organic chemistry functional groups are submolecular structural motifs. Then try going through and looking at the structures and naming them. Every functional group below is eventually discussed at one point or another in the book. Alkyne.

Aldehyde Aldehyde RCHO oxo- -al :Acetaldehyde (Ethanal) Alkane Alkyl RHn alkyl- -ane Methane Alkene Alkenyl R2C=CR2 alkenyl- -ene Ethylene (Ethene) Alkyne Alkynyl RC≡CR' alkynyl- -yne Acetylene (Ethyne) Amide Carboxami RCONR2 de carboxamid o- -amide Acetamide (Ethanamide) Amines Primary amine RNH2 amino-amine Methylamine (Methanamine) R2NH amino-amine Dimethylamine Secondary amine 25 .

Tertiary amine R3N amino- -amine Trimethylamine 4° ammonium ion R4N+ ammonio- -ammonium Choline Azo Azo compound (Diimide) RN2R' azo- -diazene Methyl orange Toluene derivative Benzyl RCH2C6H5 RBn benzyl- 1(substituent)tol uene Benzyl bromide (1-Bromotoluene) Carbonate Carbonate ROCOOR ester alkyl carbonate Carboxylate Carboxylat e RCOO− carboxy- -oate Sodium acetate (Sodium ethanoate) Carboxylic Carboxyl acid RCOOH carboxy- -oic acid Acetic acid (Ethanoic acid) Cyanate Cyanates Thiocyanat e Ether Ester ROCN RSCN ROR' RCOOR' cyanatothiocyanatoalkoxy- alkyl cyanate alkyl thiocyanate alkyl alkyl ether -oate Ethyl butyrate Diethyl ether (Ethoxyethane) Ether Ester 26 .

(Ethyl butanoate) Haloalkane Halo RX haloalkyl halide Chloroethane (Ethyl chloride) Hydroperox ide (see Hydropero organic xy peroxide) ROOH hydroperox alkyl yhydroperoxide Methyl ethyl ketone peroxide imino-imine Primary RC(=NH)R' ketimine Secondary RC(=NR)R' ketimine Imine Primary RC(=NH)H aldimine imino- -imine imino- -imine Secondary RC(=NR')H aldimine Isocyanide Isocyanide Isocyanate Isocyanates Isothiocyan ate RNC RNCO RNCS imino- -imine alkyl isocyanide alkyl isocyanate isocyanoisocyanato- isothiocyan alkyl atoisothiocyanate Allyl isothiocyanate keto-. oxo-one Ketone Ketone RCOR' Methyl ethyl ketone (Butanone) Nitrile Nitrile RCN cyano- alkanenitrile alkyl cyanide Benzonitrile (Phenyl cyanide) Nitro compound Nitroso compound Nitro Nitroso RNO2 RNO 27 nitroNitromethane nitroso- .

Nitrosobenzene Peroxide Peroxy ROOR peroxyalkyl peroxide Di-tert-butyl peroxide Benzene derivative Phenyl RC6H5 phenyl- -benzene Cumene (2-phenylpropane) Phosphine Phosphino R3P phosphino-phosphane Methylpropylphosp hane DNA Phosphodie Phosphate HOPO(OR)2 ster phosphoric di(substituent) acid hydrogenphosp di(substitue hate nt) ester phosphonosubstituent phosphonic acid Phosphonic Phosphono acid RP(=O) (OH)2 Benzylphosphonic acid Phosphate Phosphate ROP(=O) (OH)2 phospho4-pyridyl (pyridin-4yl) Glyceraldehyde 3phosphate Pyridine derivative Pyridyl RC5H4N 3-pyridyl (pyridin-3yl) 2-pyridyl (pyridin-2yl) -pyridine Nicotine Sulfide RSR' di(substituent) sulfide Dimethyl sulfide Sulfone Sulfonyl RSO2R' sulfonyl- di(substituent) sulfone Dimethyl sulfone (Methylsulfonylmet hane) 28 .

the group is referred to more properly as a polyatomic ion or complex ion. by a meaning of the term radical that predates the free radical.Sulfonic acid Sulfo RSO3H sulfo- substituent sulfonic acid Benzenesulfonic acid Sulfoxide Sulfinyl RSOR' sulfinyl- di(substituent) sulfoxide Diphenyl sulfoxide Thiol Sulfhydryl RSH mercapto-.org/wiki/Organic_Chemistry/Overview_of_Functional_Groups" MODUL IV IV. Combining the names of functional groups with the names of the parent alkanes generates a powerful systematic nomenclature for naming w:organic compounds. Reaksi addisi C = C + H2 b. And all of these are called radicals. Retrieved from "http://en. The non-hydrogen atoms of functional groups are always associated with each by covalent bonds. JENIS-JENIS REAKSI DALAM SENYAWA ORGANIK Jenis-jenis reaksi pada senyawa organic a. as well as with the rest of the molecule. Reaksi substitusi RX + OHROH + X29 CH – CH . When the group of atoms is associated with the rest of the molecule primarily by ionic forces. The first carbon after the carbon that attaches to the functional group is called the alpha carbon. sulfanyl- -thiol Ethanethiol (Ethyl mercaptan) Note: The table above is adapted from the Functional Groups table on Wikipedia.wikibooks.

Trivial : a. Nama dagang 30 JENIS-JENIS SENYAWA ORGANIK .c. Reaksi oksidasi RCH2OH + KMnO4 e. reaksi radikal. Reaksi penataan ulang (rearrangement) H3C-H2C-CH=CH-CH=CH2 H3C-H2C=CH-CH=CH-CH3 Pada dasarnya jenis-jenis reaksi pada senyawa organic ada 3 ienis yakni reaksi polar. Reaksi eliminasi RCHX-CH3 d. Alkana Rumus umum senyawa alkana adalah CnH2n+2 Pemberian nama senyawa organic dengan dua standar : 1. IUPAC 2. Reaksi reduksi RCN + LiAlH4 RCH2NH2 RC =O H RCH=CH2 + HX f. Kecepatan dan mekanisme reaksi senyawa organic Energi ikatan pada senyawa organic MODUL V V. dan reaksi perisiklik.

Nama sumber c. Nama local d Nama penemu Pemberian nama pada deret homolog senyawa alkana dengan dua cara yaitu : IUPAC ( International Union Pure and Applied Chemistry ) Rantai molekul lurus Tata nama senyawa homolog hidrokarbon pada senyawa organic rantai lurus menurut IUPAC adalah berdasarkan jumlah atom karbonnya sebagai berikut : Senyawa CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 C3000H6002 Nama Metana Etana Propane Butane Pentane Heksana Heptana Oktana Nonana Dekana Undekana Dodekana Tridekana Tetradekana Pentadekana Heksadekana Heptadekana Oktadekana Nonadekana Eikosana Heneikosana Dokosana Trikosana Tetrakosana Pentakosana Heksakosana Heptakosana Oktakosana Nonakosana Triakontana Hentriakontana Dotriakontana Tritriakontana Hektana Diktana Triktana kiliana Dilianatana Triliana Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 C41H58 C42H60 C43H62 C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C500H10002 C600H1202 Nama tetratriakontana pentatriakontana heksatriakontana heptatriakontana oktatriakontana nonatriakontana Tetrakontana hentetrakontana Dotetrakontana Tritetrakontana tetratetrakontana pentatetrakontana heksatetrakontana heptatetrakontana oktatetrakontana nonatetrakontana Pentakontana Henpentakontana dopentakontana tripentakontana tetrapentakontana pentapentakontana heksapentakontana heptapentakontana Oktapentakontana nonapentakontana Heksa kontana HenHeksa kontana doHeksa kontana triHeksa kontana tetraHeksa kontana pentaHeksa kontana heksaHeksa kontana Tetraktana Pentaktana Heksaktana Tetraliana Penliaana Heksaliana Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 C74H150 C75H152 C76H154 C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C700H14002 C800H16002 C900H18002 Nama heptaHeksa kontana oktaHeksa kontana nonaHeksa kontana Heptakontana henHeptakontana DoHeptakontana triHeptakontana tetraHeptakontana pentaHeptakontana heksaHeptakontana heptaHeptakontana oktaHeptakontana nonaHeptakontana Oktakontana henOktakontana doOktakontana triOktakontana tetraOktakontana pentaOktakontana heksaOktakontana heptaOktakontana oktaOktakontana nonaOktakontana Nonakontana henNonakontana doNonakontana triNonakontana tetraNonakontana pentaNonakontana heksaNonakontana HeptaNonakontana oktaNonakontana nonaNonakontana Heptaktana Oktaktana Nonaktana Heptaliana Oktaliana Nonaliana Rantai molekul bercabang 31 .b.

rantai dasar ditentukan berdasarkan rantai molekul terpanjang. Bila ada beberapa gugus yang sama tersubstitusi pada rantai utama maka dinamai dengan awalan di.CH-CH2-CH2-CH-CH-CH3 1 (CH2)5-CH3 CH2CH3 CH3 7 isobutil. Rantai molekul lurus bercabang lurus Untuk pemberian nama senyawa hidrokarbon berantai molekul lurus bercabang didasarkan pada aturan berikut : a. 9 trimetil undekana CH3 d. 10 etil. Contoh 11 10 9 8 7 6 5 4 3 2 1 H3C-CH2-CH-CH2-CH2-CH-CH2-CH2-CH2-CH-CH3 CH3 CH3 2. tri dan seterusnya. 9 propil.Untuk rantai molekul bercabang harus dipenuhi kaidah rantai lurus dan rantai lingkar.6. Penomoran atom karbon pada hidrokarbon dimulai pada gugus tersubstitusi yang paling dekat ke ujung rantai. 9 trimetil undekana Rantai molekul lurus bercabang lingkar H3C-CH2-CH-CH2-CH2-CH-CH2-CH2-CH2 CH3 32 . 11 metil. b. 14 15 16 17 18 19 20 CH3-CH2 7 CH3-(CH2)2 8 9 10 11 CH3 12 13 CH2-CH2-CH2-CH2-CH2-CH2-CH3 H3C-CH2-CH-CH2-CH . c. 13 isopropil eikosana Tulisan berwarna biru menunjukkan rantai utama sedangkan tulisan berwarna merah menunjukkan substituen.6. Urutan gugus tersubstitusi dimulai dari gugus berurutan dimulai berdasrkan abjad atau nomor urut gugus yang paling dekat ke awal rantai 11 10 9 8 7 6 5 4 3 2 1 H3C-CH2-CH-CH2-CH2-CH-CH2-CH2-CH2-CH-CH3 CH3 CH3 2.

Siklo butana e. the free encyclopedia Jump to: navigation. search 33 . Rantai lingkar a. Siklo heksana g. Siklo propana b. Siklo oktana IUPAC nomenclature of organic chemistry From Wikipedia. Siklo pentana f.Nonil sikloheksana rantai molekul lingkar bercabang lingkar Rantai molekul lingkar terkondensasi.

are not taken into consideration for grouping alphabetically. the number will be written twice. -al. For ordinary communication. often derived from the source of the compound (See Sec 14. If there are two side-chains with the same alpha carbon. Identify the side-chains and number them. etc.e. for example.) is written before the name of the functional group suffix (such as -ol. thereby reducing ambiguity. and every name corresponds to only one structure of molecules (i. it need not be numbered. etc. every organic compound should have a name from which an unambiguous structural formula can be drawn. If there is more than one of the same type of side-chain.).5-trimethylhexane (2 + 2 + 5 = 9) is preferred over 2. if any. Otherwise the common or trivial name may be used. (The prefixes di-. The main idea of IUPAC nomenclature is that every compound has one and only one name. tri-. The number (in Arabic numerals. Ideally.e.) before it. 2.. Identify the position of the functional group in the chain.. below) Basic principles In chemistry. but the sum of the numbers of the former is less. as they both start with '2'. 2.3-trimethyl. Different side-chains and functional groups will be grouped together in alphabetical order. use the one with highest precedence as shown here) 1. and name them by the name of their ions (Such as hydroxy for -OH. See also phanes nomenclature of highly complex cyclic molecules. In the event of the first numbers being the same for two methods of numbering.2.The IUPAC nomenclature of organic chemistry is a systematic method of naming organic chemical compounds as recommended[1] by the International Union of Pure and Applied Chemistry (IUPAC). or when the IUPAC name is simpler (viz. The numbers for that type of side chain will be grouped in ascending order and written before the name of the side-chain. ethanol against ethyl alcohol). Number the carbon atoms in the parent chain... -one. number in both directions. There is also an IUPAC nomenclature of inorganic chemistry. 1. 4. a number of prefixes. suffixes and infixes are used to describe the type and position of functional groups in the compound. i. oxyalkane for O-R. The steps to naming an organic compound are: 1. if any (If more than one. a one-one relationship). the sum of the numbers of the side chains should be made the least possible. Side chains are the carbon chains that are not in the parent chain. add the prefix (di-. tri-. For 34 . the official IUPAC naming recommendations are not always followed in practice except when it is necessary to give a concise definition to a compound.. NOTE: If there are no functional groups.2. etc. 3. 3. to spare a tedious description. Identify the remaining functional groups. The functional group should end up the least number possible (as there are two ways of numbering—right to left and left to right).5trimethylhexane (2 + 5 + 5 = 12). Identify the parent hydrocarbon chain (The longest continuous chain of carbon atoms) 2. 2. Example: 2. but are branched off from it.5. oxy for =O . Identify the functional group. find the numbers of the side-chains (the carbon chains that are not in the parent chain) in both directions. If the group is a group that can only exist at the end of any given chain (such as the carboxylic acid and aldehyde groups). etc. The end result should be such that the first number should be the least possible.).

5.have been used just to show their usage.after #.) Example: Here is a sample molecule with the parent carbons numbered: For simplicity. 6. here is an image of the same molecule. 5.) In the case of there being both side chains and secondary functional groups. tri. The "di" is not considered in both cases. Arrange everything like this: Group of side chains and secondary functional groups with numbers made in step 3 + prefix of parent hydrocarbon chain (eth. The finalized name should look like this: #. For example a double bond between carbon atoms 3 and 4 is numbered as 3-ene. tri-. Multiple bonds of one type (double/triple) are named with a prefix (di-. Number them with the number of the carbon atom at the head of the bond (i. Identify double/triple bonds. Successive words are merged into one word (trimethyl hexane becomes trimethylhexane) NOTE: IUPAC uses one-word names throughout.g.#. then use "ene" before "yne" e. meth) + double/triple bonds with numbers (or "ane") + primary functional group suffix with numbers. Add punctuation: 1.and tri. they should be written mixed together in one group rather than in two separate groups. If both types of bonds exist. you use the prefix(di-. Put a hyphen between a number and a letter (2 5 5 trimethylhexane becomes 2.5trimethylhexane) 3.e the carbon atom with the lesser number that it is attached to). Put commas between numbers (2 5 5 becomes 2. The group secondary functional groups and side chains may not look the same as shown here. as the side chains and secondary functional groups are arranged alphabetically.after #. (di. "6 13 diene 19 yne"If all bonds are single.5) 2.# . etc. This is why all parts are connected. use "ane">-#.example.#-di<side chain>-#-<secondary functional group><-#-<side chain>-#.#. Wherever it says "with numbers".).#-tri<secondary functional group><parent chain suffix><If all bonds are single bonds. The di.#. use "ane" without any numbers or prefixes. ethyl comes before dihydroxy or dimethyl. where the hydrogens in the parent chain are 35 . as the "e" in "ethyl" precedes the "h" in "hydroxy" and the "m" in "dimethyl" alphabetically.#-di<double bonds>-#-<triple bonds>-#-<primary functional group> NOTE: # is used for a number. tri-) 7. etc. it is understood that between the word and the numbers.5.

but it is a methoxy functional group There are two ethyl.at carbon 5. The parent hydrocarbon chain has 23 carbons. As there are two. an ethyl.) 2.8-diethyl.13-diene-19-yne-3.8-diethyl-5-hydroxy-15-methoxy 3. and a butyl.9-dione.8-diethyl-5hydroxy-15-methoxytricos-6. The side chains are: an ethyl. There is one triple bond between carbon atoms 19 & 20.at carbon 15. The first few are: Numb 1 2 3 4 5 6 7 8 9 10 11 36 12 13 14 15 20 30 . and the ketones are numbered 3 & 9.at carbon 12. The functional groups with the highest precedence are the two ketone groups.8-diethyl. when numbering from left to right. and a bromo. The sum of 3 & 9 (12) is less than the sum of 15 & 21 (36).at carbon 4. 4.removed and the carbons are shown by their numbers: Now. 3. o o Alkanes Main article: Alkanes Straight-chain alkanes take the suffix "-ane" and are prefixed depending on the number of carbon atoms in the chain.13diene-19-yne-3. The numbering of the molecule is based on the ketone groups. Grouped with the side chains. 1. It will be called 19-yne 4.9-dione The final name is 18-bromo-12-butyl-11-chloro-4. 2. we write 3. There are two double bonds: one between carbons 6 & 7. we get 18bromo-12-butyl-11-chloro-4.groups. Therefore. The side chains shall be grouped like this: 12-butyl-4. (But this is not the final grouping. 2. as functional groups may be added in between. the numbering is done left to right. following standard rules. It is called tricos-.at carbon 8. a methoxy.13-diene.at carbon 11. NOTE:The -O-CH3 at carbon atom 15 is not a side chain.at carbon 18. the ketone groups get numbered 3 and 9.9-dione. the ketone groups get numbered 15 and 21. we go by the steps: 1. and one between carbons 13 & 14. a chloro.when numbering from right to left. They will be called 6. The arrangement(with punctuation) is: 18-bromo-12-butyl-11-chloro-4. so they are combined to create.8-diethyl-5-hydroxy-15-methoxytricos-6. The secondary functional groups are: a hydroxy. The groups are on carbon atoms 3 & 9.

(CH3)2CHCH3. 37 . The names of the first four alkanes were derived from methanol. then numbering is chosen so that the smallest number is used. (CH3)2CHCH2CH3 (isopentane) is named 2-methylbutane. not 3-methylbutane. and the nine-carbon alkane CH3(CH2)7CH3 is named nonane. Cyclic alkanes are simply prefixed with "cyclo-". for example C4H8 is cyclobutane and C6H12 is cyclohexane. propionic acid and butyric acid. it is easier and more logical to call it simply methylpropane . depending on which end of the alkane chain is counted as "1". If there is ambiguity in the position of the substituent. ether. the simplest alkane is CH4 methane.the methyl group could not possible occur on any of the other cabon atoms (that would lengthen the chain and result in butane. The rest are named with a Greek numeric prefix. with the exceptions of nonane which has a Latin prefix. However. is treated as a propane chain with a methyl group bonded to the middle (2) carbon. commonly known as isobutane. and undecane and tridecane which have mixedlanguage prefixes. For example. not propane) and therefore the use of the number "2" is not necessary. and given the systematic name 2methylpropane. For example. counting from the end of the alkane chain. Branched alkanes are named as a straight-chain alkane with attached alkyl groups. although the name 2-methylpropane COULD be used. They are prefixed with a number indicating the carbon the group is attached to. respectively.er of carbo ns Prefix Met Pro Pen He Hep No De Unde Dode Tride Tetrade Pentade Eico Triaco Eth But Oct h p t x t n c c c c c c s nt For example.

and para.. in which case the position of substituents are numbered around the ring structure.3-dimethylbenzene.4-dimethylbenzene. the three isomers of xylene CH3C6H4CH3.g.g. the order of precedence determines which groups are named with prefix or suffix forms.If there are multiple side-branches of the same size alkyl group. and many common names such as phenol. The longest possible main alkane chain is used. 3-ethyl-2. tetra-. 38 . and 1. tri. their positions are separated by commas and the group prefixed with di-. C(CH3)4 2. even though these describe equivalent structures.etc. The highest precedence group takes the suffix. furan. in which case they take the prefix "cycloalkyl-" (e.forms. meta-. . "phenyl-". being accepted as base names for compounds derived from them. Order of precedence of groups When compounds contain more than one functional group. etc. commonly the ortho-. prefixes are ignored for the purpose of alphabetical ordering of side chains (e.2-dimethylpropane). The di-. ] Cyclic compounds Cycloalkanes and aromatic compounds can be treated as the main parent chain of the compound.2dimethylbenzene. The IUPAC nomenclature scheme becomes rapidly more elaborate for more complex cyclic structures. If there are different groups.4-dimethyl-3-ethylpentane). depending on the number of branches (e. tri-. etc. For example. therefore 3-ethyl-4-methylhexane instead of 2. with notation for compounds containing conjoined rings.3-diethylpentane. "cyclohexyl-") or for benzene. not 2. 1.4-dimethylpentane. indole. separated by commas or hyphens: 3-ethyl-4-methylhexane. The cyclic structures can also be treated as functional groups themselves. are 1. they are added in alphabetical order.g.

double and triple bonds only take suffix form (-en and -yn) and are used with other suffixes. The pattern can be seen below. However. Number of carbons Prefix as in new Common name for system alcohol Common name for aldehyde Common name for acid 1 Meth Methyl alcohol (wood alcohol) Formaldehyde Formic acid 2 Eth Ethyl alcohol (grain Acetaldehyde alcohol) Acetic acid 3 Prop Propyl alcohol Propionaldehyde Propionic acid 4 But Butyl alcohol Butyraldehyde Butyric acid 5 Pent Amyl alcohol Valeraldehyde Valeric acid 6 Hex - Caproaldehyde Caproic acid 7 Hept Enanthyl alcohol Enanthaldehyde Enanthoic acid 8 Oct Capryl alcohol Caprylaldehyde Caprylic acid 9 Non - Pelargonaldehyde Pelargonic acid 10 Dec Capric alcohol Capraldehyde Capric acid 12 Dodec Lauryl alcohol Lauraldehyde Lauric acid 14 Tetradec 39 Myristaldehyde Myristic acid . Instead of using the prefixes for the carbon skeleton above.trivial names Common nomenclature is an older system of naming organic compounds.with all others taking the prefix form. Common nomenclature . another system is used.

• • Formaldehyde Acetaldehyde Ions The IUPAC nomenclature also provides rules for naming ions. 40 . deuterons and tritons are all hydrons. Hydron Hydron is a generic term for hydrogen cation. protons.16 Hexadec Cetyl alcohol Palmitaldehyde Palmitic acid 17 Heptadec - - Margaric acid 18 Octadec Stearyl alcohol Stearaldehyde Stearic acid 20 Icos Arachidyl alcohol - Arachidic acid 22 Docos Behenyl alcohol - Behenic acid 24 Tetracos Lignoceryl alcohol - Lignoceric acid 26 Hexacos Cerotinyl alcohol - Cerotinic acid 28 Octacos Montanyl alcohol - Montanic acid 30 Triacont Melissyl alcohol - Melissic acid Aldehydes The common name for an aldehyde is derived from the common name of the corresponding carboxylic acid by dropping the word acid and changing the suffix from -ic or -oic to -aldehyde.

R-CH2X+ R’Na d. organic. Cations and substitution The above cations except for methanium are not. "tri-" as with halogenation. HO-O+H2 is dioxidanium (HO-OH is dioxidane). since they do not contain carbon. nama sumber Sintesa alkana H2O a. and H2F+ is fluoronium. chalcogen or nitrogen-family element then the suffix "-ium" is added to the name of the neutral hydride after dropping any final 'e'. which commonly refers to NO2+. C = C + H2 c. H5C+ is methanium. However. (CH3)3O+ is trimethyloxonium. nama dagang b.Parent hydride cations Simple cations formed by adding a hydron to a hydride of a halogen. then the number is indicated by prefixing with "di-". RX + Na b. and H2N-N+H3 is diazanium (H2NNH2 is diazane). strictly speaking. R-X + Mg e. many organic cations are obtained by substituting another element or some functional group for a hydrogen. The name of each substitution is prefixed to the hydride cation name. If many substitutions by the same functional group occur. nama lokal c. Ammonium was adopted instead of nitronium. If the cationic center of the hydride is not a halogen. RC CH + H2 R-R + NaX CH – CH RCH2-R’ + NaX RCH2-CH3 RMgX + H2O CH4 + H2O 41 RH + MgXOH e. Nama trivial ( nama lain ) Nama trivial adalah penamaan senyawa hidrokarbon tidak dengan sistematika seperti pada aturan pemberian nama menurut IUPAC. chalcogen or nitrogen-family element are named by adding the suffix "-onium" to the element's root: H4N+ is ammonium. CH3F3N+ is trifluoromethylammonium. H3O+ is oxonium. nama penemu d. tetapi dengan nama tertentu seperti : a. CO + 3H2 .

etc. senyawa Alkena alifatik mempunyai struktur molekul terbuka seperti berikut : R-CH = CH2 Tabel 5.Alkena Main articles: Alkenes and Alkynes Alkenes are named for their parent alkane chain with the suffix "-ene" and an infixed number indicating the position of the double-bonded carbon in the chain: CH2=CHCH2CH3 is but-1-ene. Contoh Senyawa CH4 C2H6 C3H8 C4H10 C5H12 Nama Metena Etena Propena Butena Pentena Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 Nama tetratriakontena pentatriakontena heksatriakontena heptatriakontena oktatriakontena Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 Nama heptaHeksa kontena oktaHeksa kontena nonaHeksa kontena Heptakontena henHeptakontena 42 . Alkynes are named using the same system. Simple cis and trans isomers are indicated with a prefixed cis.or trans-: cis-but-2-ene.3-diene. -triene. Nama alkena alifatik sesuai dengan deret homolog alkana. trans-but-2-ene. Pemberian nama a. akhiran nama ana diganti dengan ena.. with the suffix "-yne" indicating a triple bond: ethyne (acetylene). Alkena alifatik aa. propyne (methylacetylene). More complex geometric isomerisations are described using the Cahn Ingold Prelog priority rules. with the size prefix of the chain taking an extra "a": CH2=CHCH=CH2 is buta-1. Multiple double bonds take the form -diene.

alkapoliena Nama senyawa alkapoliena alifatik disesuaikan dengan nama homolog alkana.3. akhiran ana diganti menjadi poliena tergantung banyaknya gugus ena yang terdapat dalam senyawa tersebut contoh : 1 2 3 4 5 6 7 8 9 10 CH2=CH-CH=CH-CH2-CH=CH-CH2-CH = CH2 1.C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 C3000H6002 Heksena Heptena Oktena Nonena Dekena Undekena Dodekena Tridekena Tetradekena Pentadekena Heksadekena Heptadekena Oktadekena Nonadekena Eikosena Heneikosena Dokosena Trikosena Tetrakosena Pentakosena Heksakosena Heptakosena Oktakosena Nonakosena Triakontena Hentriakontena Dotriakontena Tritriakontena Hektena Diktena Triktena Kiliena Diliena Triliena C39H54 C40H56 C41H58 C42H60 C43H62 C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C5000H10002 C6000H1202 nonatriakontena Tetrakontena hentetrakontena Dotetrakontena Tritetrakontena tetratetrakontena pentatetrakontena heksatetrakontena heptatetrakontena Oktatetrakontena nonatetrakontena Pentakontena Henpentakontena dopentakontena tripentakontena tetrapentakontena pentapentakontena heksapentakontena heptapentakontena Oktapentakontena nonapentakontena Heksa kontena HenHeksa kontena doHeksa kontena triHeksa kontena tetraHeksa kontena pentaHeksa kontena heksaHeksa kontena Tetraktena Pentaktena Heksaktena Tetraliena Pentaliena Heksaliena C72H146 C73H148 C74H150 C75H152 C76H154 C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C7000H14002 C8000H16002 C9000H18002 DoHeptakontena triHeptakontena tetraHeptakontena pentaHeptakontena heksaHeptakontena heptaHeptakontena oktaHeptakontena nonaHeptakontena Oktakontena henOktakontena doOktakontena triOktakontena tetraOktakontena pentaOktakontena heksaOktakontena heptaOktakontena oktaOktakontena nonaOktakontena Nonakontena henNonakontena doNonakontena triNonakontena tetraNonakontena pentaNonakontena heksaNonakontena HeptaNonakontena oktaNonakontena nonaNonakontena Heptahektena Oktaktena Nonaktena Heptaliena Oktaliena Nonaliena CH3-CH2-CH2-CH = CH2 Pentena b.Alkena siklik 43 .9 dekatetraena Pada senyawa ini Karenna ada 4 gugus ena maka namanya mendapat akhiran tetraena c.6.

If the alkene contains only one double bond and that double bond is terminal (the double bond is at one end of the molecule or another) then it is not necessary to place any number in front of the name. The numbers should go from lowest to highest. butane: C4H10 (CH3CH2CH2CH3) butene: C4H8 (CH2=CHCH2CH3) If the double bond is not terminal (if it is on a carbon somewhere in the center of the chain) then the carbons should be numbered in such a way as to give the first of the two double-bonded carbons the lowest possible number.5-diene: CH2=CHCH2CH2CH=CHCH2CH2CH2CH3 Note that the numbering of "2-4" above yields a molecule with two double bonds separated by just one single bond. as shown below. but the "-ane" suffix is changed to "-ene". Alkenes can present a unique problem. correct: pent-2-ene (CH3CH=CHCH2CH3) incorrect: pent-3-ene (CH3CH2CH=CHCH3) The second one is incorrect because flipping the formula horizontally results in a lower number for the alkene. we discussed cis/trans notation where cis. it stays on that side. EZ Notation Earlier in stereochemistry. and be separated from one another by a comma. Naming Alkenes Alkenes are named as if they were alkanes. all of the bonds should be numbered in the name of the molecule . If there is more than one double bond in an alkene. 44 .Siklopropena siklobutadiena siklopentena Alkenes are aliphatic hydrocarbons containing carbon-carbon double bond and general formula CnH2n.4-diene: CH3CH=CHCH=CHCH2CH2CH3 deca-1. and they represent an enhanced stability of conformation.means same side and transmeans opposite side. octa-2. Double bonds in such a condition are called "conjugated". so they are energetically favored as reactants in many situations and combinations. The first thing to keep in mind is that alkenes are planar and there's no rotation of the bonds. as we'll discuss later. and that number should precede the "ene" suffix with a dash. however in that the cis/trans notation sometimes breaks down. So when a substituent is on one side of the double-bond.even terminal double bonds. The IUPAC numerical prefixes are used to indicate the number of double bonds.

The priority is based on the atomic number of the substituents. so we go out to the next bond. On the left. so the priorities are the same as in the Zusammen version. The system takes a little getting used to and it's usually easier to name an alkene than it is to write one out given its name. how would you use cis and trans? Which is the same side and which is the opposite side? Whenever an alkene has 3 or 4 differing substituents. these are Entgegen. we assign a substituent as being either a high priority or low priority substituent. So the top gets high priority and the bottom gets low priority. so we have trans-but-2ene. However. But with a little practice. same sides (zame zides) of double bond Let's begin with (Z)-3-methylpent-2-ene. one must use the what's called the EZ nomenclature. (Z)-3-methylpent-2-ene and (E)-3-methylpent-2-ene From the example above. we have carbon substituents on both the top and bottom. so it's cis-but-2-ene. So in this situation. Now let's look at (E)-3-methylpent-2-ene. but on the bottom. On to the top. or opposite. On the left. opposite sides of double bond Z: Zusammen.cis-but-2-ene and trans-but-2-ene The above example is pretty straight-forward. a hydrogen. the cis/trans notation works and. the substituents are reversed on the right side with the high priority substituent on the bottom and the low priority substituent on the top. And on the right. coming from the German words. you'll find that it's quite easy. On the right side. hydrogen is the lowest priority because its atomic number is 1 and carbon is higher because its atomic number is 6. these are the correct names. E: Entgegen. think 'Zame Zide'). So on the left side. we have two methyl groups on the same side. Because the high priorities from both sides are on the same side. We begin by dividing our alkene into left and right halves. in fact. we have the same substituents on the same sides. we have them on opposite sides. Because the High and Low priorities are opposite on the left and right. they are Zusammen (as a mnemonic. 45 . there's another carbon. Entgegen (opposite) and Zusammen (same). On each side.

e. The general formula for an aliphatic alkene is: CnH2n -. alkenes have very limited rotation around the double bonds between two atoms. at least one carbon-to-carbon double bond. For example. cis-trans should only be used if each double-bonded carbon atom has a hydrogen atom (i.g. This correspondence is exact only if the two carbon atoms are identically substituted. but-2-ene exists as two diastereomers: (Z)-but-2-ene (E)-But-2-ene 46 . That is.which would require about 60 or 70 kcal of energy.Comparison of E-Z with cis-trans (Z)-but-2-ene (E)-but-2-ene cis-but-2-ene trans-but-2-ene To a certain extent.e. share one pair of electrons in a pi (π) bond between them. R-CH=CH-R'). IUPAC Gold book on E-Z notation. where the carbon atoms.isomer and the E as the transisomers. For this reason alkenes have different chemical properties based on which side of the bond each atom is located. C2H4 or C3H6 Diastereomerism Restricted rotation Because of the characteristics of pi-bonds. to say. IUPAC Gold book on cis-trans notation. the Z configuration can be regarded as the cis. In order for the alkene structure to rotate the pi-bond would first have to be broken . in addition to an electron pair shared in a sigma (σ) bond. In general. Properties Alkenes are molecules with carbons bonded to hydrogens which contain at least two sp2 hybridized carbon atoms.

we'll only describe briefly in this chapter and instead. the more stable that alkene is. This illustrates that there are differences in the stabilities of the three species of butene isomers. In the middle of a chain. • In general. A trans double bond is more stable than a cis double bond. and is called primary (1°). due to the difference in how much energy can be released by reducing them.[1] Some of these methods. The most stable would be quaternary (4°). a double bond could be connected to two carbons. we can see that all of the products are butane. Primary carbons are the least stable. and (E)-2-butene. • Reactions Preparation There are several methods for creating alcohols. This is called secondary (2°). -28. the more and the bulkier the alkyl groups on a sp2-hybridized carbon in the alkene. The relative stability of alkenes may be estimated based on the following concepts: • An internal alkene (the double bond not on the terminal carbon) is more stable than a terminal alkene (the double bond is on a terminal carbon). cover them in more detail later in the book.6 kcal/mol for (Z)-2-butene and -27.cis-but-2-ene trans-but-2-ene Relative stability Observing the reaction of the addition of hydrogen to 1-butene.3 kcal/mol for 1-butene. the double bond is only connected to one carbon. (Z)-2-butene. Internal alkenes are more stable than terminal alkenes because they are connected to more carbons on the chain.6 kcal/mol for (E)-2-butene. Dehydrohalogenation of Haloalkanes 47 . Since a terminal alkene is located at the end of the chain. it's enough to know that they are ways of creating alkenes. such as the Wittig reaction. The difference between the reactions is that each reaction has a different energy: -30. For now.

creating a carbocation. or it can be performed using zinc dust in a solution of either heated ethanol or acetic acid. This reaction can also be performed with magnesium in ether. creating the alkene. Dehalogenation of Vicinal Dibromides Synthesis of alkene via debromination of vicinal dihalides using Sodium Iodide Synthesis of alkene via debromination of vicinal dihalides using Zinc The dehalogenation of vicinal dihalides (halides on two neighboring carbons. This create a hydronium ion which easily leaves the carbon. The acid. a hydrogen from an adjacent bond leaves. The reaction can take place using either sodium iodide in a solution of acetone.Synthesis of alkene by dehydrohalogenation Dehydrohalogenation is a very common method for creating alkenes. Dehydration of alcohols Synthesis of alkene by dehydration of an alcohol When an alcohol is treated with a strong acid. for example H2SO4. and the carbocation wanting to stabilize and get a bond. though the mechanism is different as this actually produces. The haloalkane must have a hydrogen and halide 180° from each other on neighboring carbons. If there is no hydrogen 180° from the halogen on a neighboring carbon. resulting in the alkene. the reaction will not take place. 48 . without its electron. The underlying mechanism is the E1 mechanism which is described below. it is converted into an alkene. as an intermediate. think "vicinity") is another method for synthesizing alkenes. and the adjacent carbons form a pi bond. The base used is generally a strong base such as KOH (potassium hydroxide) or NaOCH3 (sodium methoxide). It uses the E2 elimination mechanism that we'll discuss in detail at the end of this chapter. now deficient a proton. A lone pair from the alcohol's oxygen attacks a proton (H+) from the acid. The mechanism of this reaction is fairly straight-forward. a Grignard reagent that reacts with itself and and causes an elimination.

or partial positive charge in the case of a transition state. His rule states:"When an unsymmetrical alkene reacts with a hydrogen halide to give an alkyl halide. Usually hydrogen plays the role of the electrophile.Wittig Reaction Synthesis of alkene via Wittig reaction Markovnikov's Rule Before we continue discussing reactions. the Carbon with the most Hydrogens gets another Hydrogen and the one with the least Hydrogens gets the halogen) This means that the nucleophile of the electophile-nucleophile pair is bonded to the position most stable for a carbocation." Aka. Examples CH2 = CH − CH3 + H − Br − > CH3 − CHBr − CH3 Here the Br attaches to the middle carbon over the terminal carbon. hydrogen ends up on the more substituted carbon of the double bond. hydrogen can also act as an nucleophile in some reactions. is an example of this." This is a simple rule stated by the Russian Vladmir Markovnikov in 1869. however. as are reactions that are conducted in peroxides. we need to take a detour and discuss a subject that's very important in Alkene reactions. and this is called a Markovnikov product. Markovnikov product The product of a reaction that follows Markovnikov's rule is called a Markovnikov product. Anti-Markovnikov addition Certain reactions produce the opposite of the Markovnikov product. The original Markovnikov rule predicts that the hydrogen (an electrophile) being added across a double bond will end up on the carbon with more hydrogens. yielding what is called antiMarkovnikov product. as he was showing the orientation of addition of HBr to alkenes. because of Markovnikov's rule. in Markovnikov addition Markovnikov addition is an addition reaction which follows Markovnikov's rule. Generalizing to all electrophiles. and the halogen to the carbon of the alkene with the fewer number of hydrogen substituents" (This rule is often compared to the phrase: "The rich get richer and the poor get poorer. producing a Markovnikov product. the hydrogen adds to the carbon of the alkene that has the greater number of hydrogen substituents. That is. The hydroboration/oxidation reaction that we'll discuss shortly. it is really the electrophile which ends up on the carbon with the greatest number of hydrogens. The following expansion of Markovnikov's rule is more versitile: 49 . A modernized version of Markovnikov's rule often explains the "anti-Markovnikov" behavior. "Markovnikov's Rule.

The result is that the filled C-H σ orbital interacts with the unfilled C-C π orbital and stabilizes the molecule. the electrophile adds to the carbon with the greatest number of hydrogen substituents. HBr in Hydrogen Peroxide: Due to formation of free radicals."When an alkene undergoes electrophilic addition. 50 . unlike in the above example. For example. the more chances there are for hyperconjugation and thus the more stable the molecule is. Why it works Markovnikov's rule works because of the stability of carbocation intermediates. where it is most stable. This leads to a stabilizing effect called hyperconjugation. the alkyl free radical forms at the middle atom. 1. and the mechanism in which it reacts. Experiments tend to reveal that carbocations are planar molecules. Addition reactions Hydroboration Hydroboration is a very useful reaction in Alkenes. The nucleophile adds to the more highly substituated carbon. Exceptions to the Rule There are a few exceptions to the Markovnikov rule. Oxymercuration produces a Markovnikov product while Hydroboration produces an antiMarkovnikov product. This gives the organic chemist a choice in products without having to be stuck with a single product that might not be the most desired. and a hydrogen attaches itself here. not as an end product so much as an intermediate product for further reactions." Or more simply: "The species that adds first adds to the carbon with the greatest number of hydrogens. with a carbon that has three substituents at 120° to each other and a vacant p orbital that is perpendicular to it in the 3rd plane. Hyperconjugation is what happens when there is an unfilled (antibonding or vacant) C-C π orbital and a filled C-H σ bond orbital next to each other. Note here hydrogen addition is the second step. The p orbital extends above and below the trisubstituent plane. The more highly substituted the molecule. The primary one we'll discuss below is the Hydroboration/Oxidation reaction which is actually an a hydroboration reaction followed by a completely separate oxidation reaction. and these are of tremendous importance to organic synthesis. Another stabilizing effect is an inductive effect. in the reactions we discuss below. we'll show two different ways of creating alcohols from alkenes: Oxymercuration-Reduction and Hydroboration/Oxidation." The fact that some reactions reliably produce anti-Markovnikov products is actually a powerful tool in organic chemistry.

This description is fairly adequate. in reality. B2H6 complex BH3-THF complex Borane. until you end up with a complex of the boron atom attached to 3 alkyl groups. the boron. in this configuration has only 6 electrons and wants 8. Hydroboration/Oxidation [2] Hydroboration/Oxidation reaction 51 . however. BH3 is often used in a complex with tetrahydrofuran (THF) as shown in the image on the right. This trialkyl-boron complex is then used in other reactions to produce various products. In the final step. As you can see from the transition state in the center of the image. this produces a sort of box between the two alkene carbons and the boron and its hydrogen. instead of using B2H6 itself. or R3B. so in its natural state it actually creates the B2H6 complex shown on the left. Hydroboration happens in what's called syn-addition because the boron and one of its hydrogens attach to the same side of the alkene at the same time. Furthermore. along with its other two hydrogens. Boron.In either situation. the result of the reactions are the same.Hydroboration mechanism The addition of BH3 is a concerted reaction in that several bonds are broken and formed at the same time. is not stable as BH3. the reaction actually continues to happen and the -BH2 continue to react with other alkenes giving an R2BH and then again. remains attached to one carbon and the other hydrogen attaches to the adjacent carbon.

Oxymercuration/Reduction [2] Oxymercuration/Reduction of 1-propene Another useful method for creating alcohols from alkenes. As mentioned in the discussion of Markovnikov's rule. Like the Hydroboration/Reduction. Hydroboration produces an antimarkovnikov product in that the hydrogen attaches to the most substituted side of the alkene instead of the least substituted side. In the first step. The reaction is carried out under pressure in the presence of a metallic catalyst. this too is a two-step process. Catalytic addition of hydrogen Catalytic hydrogenation of alkenes produce the corresponding alkanes. The result is an alcohol. this reaction. The catalytic hydrogenation of ethylene to yield ethane proceeds thusly: CH2=CH2 + H2 + catalyst → CH3-CH3 52 . Raney's nickel (an alloy of nickel and aluminium) is often employed. is Oxymercuration/Reduction. but for laboratory syntheses. The hydrogen is added to the least substituted side and the hydroxyl group is added to the most substituted side. The first step is the above described hydroboration. Here. nickel or palladium. in an anti-Markovnikov product. the mercury is reduced by the addition of sodium borohydride. the trialkyl-boron complex is oxidized with hydrogen peroxide (H2O2) in a basic solution. Unlike Hydroboration/Oxidation. as can be seen in the image above. In the second step. the hydrogen ends up on the most substituted side and the hydroxyl group on the least substituted side. After this step. follows Markovnikov's rule. Common industrial catalysts are based on platinum. Hydroboration/Oxidation of 1-propene By way of comparison. the alkene is reacted with mercury acetate in water and THF.Hydroboration/Oxidation is a 2 part reaction. here's the same reaction using the Hydroboration/Oxidation reaction.

Catalytic oxidation with oxygen or the reaction with percarboxylic acids yields epoxides. yielding two aldehydes or ketones: R1-CH=CH-R2 + O3 → R1-CHO + R2-CHO + H2O This reaction can be used to determine the position of a double bond in an unknown alkene. alkenes burn with a bright flame to carbon dioxide and water. Halogenation Addition of elementary bromine or chlorine to alkenes yield vicinal dibromo. Hydrohalogenation Addition of hydrohalic acids like HCl or HBr to alkenes yield the corresponding haloalkanes. This makes the Br closest to the double bond slightly positive and therefore an electrophile. an example of this type of reaction: CH3CH=CH2 + HBr → CH3-CHBr-CH3 If the two carbon atoms at the double bond are linked to a different number of hydrogen atoms.and dichloroalkanes. Reaction with ozone in ozonolysis leads to the breaking of the double bond. Polymerization can either proceed via a free-radical or an ionic mechanism. The decoloration of a solution of bromine in water is an analytical test for the presence of alkenes: CH2=CH2 + Br2 → BrCH2-CH2Br The reaction works because the high electron density at the double bond causes a temporary shift of electrons in the Br-Br bond causing a temporary induced dipole. respectively.Electrophilic addition Most addition reactions to alkenes follow the mechanism of electrophilic addition. the halogen is found preferentially at the carbon with less hydrogen substituents (Markovnikov's rule). In the presence of oxygen. Addition of a carbene or carbenoid yields the corresponding cyclopropane Oxidation Alkenes are oxidized with a large number of oxidizing agents. An example is the Prins reaction. Alkena aromatik 53 . such as the plastics polyethylene and polypropylene. f. where the electrophile is a carbonyl group. Polymerization Polymerization of alkenes is an economically important reaction which yields polymers of high industrial value.

2. 5. 2. Teori aromatisitas didasarkan pada sifat benzene yang mengikuti postulat Huckel berikut : 1. dari pada reaksi addisi elektrofilik yang mengakibatkan putusnya konyugasi ikatan . 3. semua ikatan -C-C-C. Benzen adalah senyawa lingkar terkonyugasi dengan rumus C6H6. Kekule Siklo heksa triena (benzena) Benzen ( Fisher ) Benzen ( Dewar ) 54 Benzen (Ladenburg ) .39 Ao 4. 4. Benzen adalah molekul simetris. dan merupakan heksagonal. Benzen bisa mengalami reaksi substitusi yang mengikuti konyugasi lingkar. berupa bidang datar. dimana n adalah bilangan bulat dari 0. Benzen biasanya tidak stabil. dan panjang semua ikatan –C-C.adalah 1.1 . 5. Panas hidrogenasinya adalah 36 kcal/mole lebih kecil dari pada panas hidrogenasi triena normal. dst. Setiap ikatan ganda karbon C=C mempunyai dua electron π Siklo heksa triena (benzen) Pada senyawa sikloheksatriena ini ada 3 x 2 = 6 elektron π. Benzen memenuhi teori hibrida resonansi yang strukturnya merupakan peralihan antara dua bentuk struktur menurut Kekule. 3.Menurut kaidah Huckel senyawa alkena menjadi aromatic apabila mempunyai jumlah electron π = 4n+2 dengan struktur senyawa lingkar.adalah 120o.

6. Ikatan pada benzen dapat lagi dengan menggunakan teori orbital molekul. Enam orbital p bergabung membentuk enem orbital molekul benzene dengan resultante delokalisasi electron melelui sistim konyugasi. . After understanding the usefulness of unsaturated compound, or conjugated system, we hope to explore the unique structure of aromatic compounds, including why benzene should not be called 1,3,5-cyclohexatriene because it is more stable than a typical triene, and seemingly unreactive. Called "aromatic" initially because of its fragrance, aromaticity now refers to the stability of compounds that are considered aromatic, not only benzene. Any cyclic compound with 4n+2 pi electrons in the system is aromatic. The stability of aromatic compounds arises because all bonding orbitals are filled and low in energy.

History of Aromatics
Early in the 19th century, advances in equipment, technique and communications resulted in chemists discovering and experimenting with novel chemical compounds. In the course of their investigations they stumbled across a different kind of stable compound with the molecular formula of C6H6. Unable to visualize what such a compound might look like, the scientists invented all sorts of models for carbon-to-carbon bonding -- many of which were not entirely stable -- in order to fit what they had observed to what they expected the C6H6 compound to look like. Benzene (which is the name that was given to the aromatic compound C6H6) is probably the most common and industrially important aromatic compound in wide use today. It was discovered in 1825 by Michael Faraday, and its commercial production from coal tar (and, later on, other natural sources) began in earnest about twenty-five years later. The structure of benzene emerged during the 1860s, the result of contributions from several chemists, most famously that of Kekulé. Scientists of the time did not have the benefit of understanding that electrons are capable of delocalization, so that all carbon atoms could share the same π-bond electron configuration equally. Huckel was the first to apply the new theory of quantum mechanics to clearly separating σ and π electrons. He went on to develop a theory of π electron bonding for benzene, which was the first to explain the electronic origins of aromaticity.

Benzene Structure
Benzene is a hexagonal ring of six carbon atoms connected to each other through one p-orbital per carbon. Its chemical formula is C6H6, and its structure is a hexagonal ring of carbons sharing symmetrical bonds, with all six hydrogen atoms protruding outwards from the carbon ring, but in the same plane as the ring. The p-orbital system contains 6 electrons, and one way to distribute the electrons yields the following structure:

However, another resonance form of benzene is possible, where the single bonds of the first structure are replaced with double bonds, and the double bonds with single bonds. These two resonance forms are co-dominant in benzene. (Other forms, such as a structure with a π bond connecting opposite carbons, are possible but negligible.) Thus, each bond in benzene has been 55

experimentally shown to be of equal length and strength, and each is accounted as approximately a "1.5" bond instead of either a single or double bond alone. Electron density is shared between carbons, in effect yielding neither a single nor a double bond, but a sort of one-and-a-half bond between each of the six carbons. Benzene has a density of negative charge both above and below the plane formed by the ring structure. Although benzene is very stable and does not tend to react energetically with most substances, electrophilic compounds may be attracted to this localized electron density and such substances may form a bond with the aromatic benzene ring. An electron delocalisation ring can be used to show in a single picture both dominant resonance forms of benzene:

Benzene Properties
Benzene is a colorless, flammable liquid with a sweet aroma and carcinogenic effects. The aromatic properties of benzene make it far different from other alkenes in many ways.

Benzene Reactions
Main article: Aromatic reactions Unlike alkenes, aromatic compounds such as benzene undergo substitution reactions instead of addition reactions. The most common reaction for benzene to undergo is electrophilic aromatic substitution (EAS), although in a few special cases, it can undergo nucleophilic aromatic substitution.

Benzene Health Effects
In the body, benzene is metabolized, and benzene exposure may have quite serious health effects. Breathing in very high levels of benzene can result in death, while somewhat lower (but still high) levels can cause drowsiness, dizziness, rapid heart rate, headaches, tremors, confusion, and unconsciousness. Eating or drinking foods containing high levels of benzene can cause vomiting, irritation of the stomach, dizziness, sleepiness, convulsions, rapid heart rate, and even death. The major effect of benzene from chronic (long-term) exposure is to the blood. Benzene damages the bone marrow and can cause a decrease in red blood cells, leading to anemia. It can also cause excessive bleeding and depress the immune system, increasing the chance of infection. Some women who breathed high levels of benzene for many months had irregular menstrual periods and a decrease in the size of their ovaries. It is not known whether benzene exposure affects the developing fetus in pregnant women or fertility in men, however animal studies have shown low birth weights, delayed bone formation, and bone marrow damage when pregnant animals breathed benzene. The US Department of Health and Human Services (DHHS) also classifies benzene as a human carcinogen. Long-term exposure to high levels of benzene in the air can cause leukemia, a 56

potentially fatal cancer of the blood-forming organs. In particular, Acute Myeloid Leukemia (AML) may be caused by benzene.

Aromaticity
Aromaticity in organic chemistry does not refer to whether or not a molecule triggers a sensory response from olfactory organs (whether it "smells"), but rather refers to the arrangement of electron bonds in a cyclic molecule. Many molecules that have a strong odor (such as diatomic chlorine Cl2) are not aromatic in structure -- odor has little to do with chemical aromaticity. It was the case, however, that many of the earliest-known examples of aromatic compounds had distinctively pleasant smells. This property led to the term "aromatic" for this class of compounds, and hence the property of having enhanced stability due to delocalized electrons came to be called "aromaticity".

Definition
Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. It can also be considered a manifestation of cyclic delocalization and of resonance. This is usually considered to be because electrons are free to cycle around circular arrangements of atoms, which are alternately single- and double-bonded to one another. These bonds may be seen as a hybrid of a single bond and a double bond, each bond in the ring identical to every other. This commonly-seen model of aromatic rings was developed by Kekulé. The model for benzene consists of two resonance forms, which corresponds to the double and single bonds' switching positions. Benzene is a more stable molecule than would be expected of cyclohexatriene, which is a theoretical molecule.

Theory
By convention, the double-headed arrow indicates that two structures are simply hypothetical, since neither can be said to be an accurate representation of the actual compound. The actual molecule is best represented by a hybrid (average) of most likely structures, called resonance forms. A carboncarbon double bond is shorter in length than a carbon-carbon single bond, but aromatic compounds are perfectly geometrical (that is, not lop-sided) because all the carbon-carbon bonds have the same length. The actual distance between atoms inside an aromatic molecule is intermediate between that of a single and that of a double bond. A better representation than Lewis drawings of double and single bonds is that of the circular π bond (Armstrong's inner cycle), in which the electron density is evenly distributed through a π bond above and below the ring. This model more correctly represents the location of electron density within the aromatic molecule's overall structure. The single bonds are sigma (σ) bonds formed with electrons positioned "in line" between the carbon atoms' nuclei. Double bonds consist of one "in line" σ bond and another non-linearly arranged bond -- a π-bond. The π-bonds are formed from the 57

There are 6 π electrons. however. The cyclobutadienide (2−) ion. from 3 double bonds). Aromatic molecules typically display enhanced chemical stability. Planar monocyclic molecules containing 4n π electrons are called antiaromatic and are. and so on) 5. π orbitals can interact with each other freely. (This is known as Hückel's rule. but the "extra" electrons strengthen all of the bonds of the ring equally. The circulating (that is. and are therefore ignored for the 4n + 2 rule. Aromatic molecules are able to interact with each other in so-called π-π stacking: the π systems form two parallel rings overlap in a "face-to-face" orientation. 58 . each electron can be shared by all the carbon atoms in an aromatic ring. is aromatic (6 electrons). In furan. Aromatic molecules are also able to interact with each other in an "edge-to-face" orientation: the slight positive charge of the substituents on the ring atoms of one molecule are attracted to the slight negative charge of the aromatic system on another molecule. and thereby they become delocalized. Contributing atoms arranged in one or more rings 4. compared to similar nonaromatic molecules. Since they are out of the plane of the atoms. Special reactivity in organic reactions such as electrophilic aromatic substitution and nucleophilic aromatic substitution Whereas benzene is aromatic (6 electrons. instead of being tied to one particular atom of carbon. so furan is aromatic. A number of pi delocalized electrons that is even. thereby becoming merely nonaromatic. Coplanar structure. 14. with all the contributing atoms in the same plane 3. but not a multiple of 4. which is not satisfied by any n integer value. delocalized) π electrons in an aromatic molecule generate significant local magnetic fields that can be detected by NMR techniques. Thus. most commonly an arrangement of alternating single and double bonds 2. An atom in an aromatic system can have other electrons that are not part of the system. Molecules that could be anti-aromatic will tend to alter their electronic or conformational structure to avoid this situation. A delocalized conjugated pi system. This means that. destabilized. in general. NMR experiments show that protons on the aromatic ring are shifted substantially further down-field than those on aliphatic carbons. One lone pair is in the π system and the other in the plane of the ring (analogous to C-H bond on the other positions). since the number of π delocalized electrons is 4. the oxygen atom is sp2 hybridized. Permissible numbers of π electrons include 6.overlap of atomic p-orbitals simultaneously above and below the plane of the ring formed by the "in line" σ-bonds. 10. cyclobutadiene is not. Characteristics An aromatic compound contains a set of covalently-bound atoms with specific characteristics: 1. there are not enough electrons to form double bonds on all the carbon atoms.

-NHR. If. depending on the group or atom in question. Generally. and many exceptions exist. and if less. But since EAS is the most common reaction with aromatic rings. but when memorizing the groups below it is helpful to also memorize whether it is O (ortho). This concept will be further discussed in the next chapter. -OStrength Directing very strong ortho/para very strong ortho/para ortho/para -NHCOCH3. the ortho positions will be largely blocked by the tert-butyl group and thus nearly all the product would be para. Another factor that heavily influences direction.Monosubstituted Benzenes Benzene is a very important basic structure which is useful for analysis and synthesis in most aspects of organic chemistry. Effects of Different Substituents Depending on the type of substituent. Activating Substituents Activating substituents make benzene either slightly more reactive or very much more reactive. In EAS. is steric hindrance. but in Nucleophilic Aromatic Substitution. which substitutents and where they are placed on the ring can be considered the most critical aspect of benzene chemistry in general. for example. when discussing activation and deactivation. Aromatic rings can undergo other types of reactions. These are the most common forms of reactions with aromatic rings. An atom or group may encourage additional atoms or groups to add or not to add to certain other carbons in relation to the carbon connected to the directing group. In general. however. M (meta) or P (para)-directing. all groups and/or substituent atoms on a benzene ring are directing. despite the fact that it is ortho/para directing. so it is best to memorize the groups listed below instead of counting on a quick and dirty rule of thumb. it's normally done in terms of the EAS. then it is called deactivating. If the atom or group makes the ring more reactive. and in the case of Nucleophilic Aromatic Substitution. The benzene ring itself is not the most interesting or useful feature of the molecule. -NRR -OH. a hydroxyl group is strongly deactivating. In addition to activating or deactivating. the activating and deactivating nature of substituents on the rings is reversed. atoms or groups of atoms may serve to make the benzene ring either more reactive or less reactive. you have a tert-butyl substituent on the ring. Group -NH2. it is called activating. however. a hydroxyl groups is strongly activating. the terms activating and deactivating are in terms of the reactions that fall into the category of Electrophilic Aromatic Substitution (EAS). if one of the major heteroatoms (nitrogen or oxygen) is directly attached to the carbon ring then the result is probably activation. -NHCOR strong 59 . This is merely a rule of thumb.

Resonance effects 2. -COR -F -Cl -Br strong weak weak weak Activation vs. Deactivation and ortho/para vs. -OR -CH3. -C2H5. -R -C6H5 strong weak very weak ortho/para ortho/para ortho/para Deactivating Substituents A deactivating group is a functional group attached to a benzene molecule that removes electron density from the benzene ring. it seems pretty clear there's a relationship. making electrophilic aromatic substitution reactions slower and more difficult than they would be on benzene alone. Group -NO2 -NR3+ -CF3. so each deactivating group is listed below along with its directing characteristic. deactivating groups may also determine the positions (relative to themselves) on the benzene ring where substitutions take place. -CO2R strong -COH. There are primarily two effects that substituents impart on the ring that affect these features: 1. CCl3 -CN -SO3H Strength Directing very strong meta very strong meta very strong meta strong strong meta meta meta meta ortho/para ortho/para ortho/para -CO2H. meta directing So why are some substituents activating or deactivating? Why are some meta directing and others ortho/para directing? From the above tables.-OCH3. Inductive effects 60 . As discussed above for activating groups.

the electrophile is attacked by pi electrons in the ring. As we've seen before in some other reactions. Resonance effects are the ability or inability of a substituent to provide electrons to the ring and enhance its resonance stability. when a carbocation is created as an intermediate. We'll discuss EAS in more detail in the next section. we must first get a basic understanding of the mechanism of Electrophilic Aromatic Subsitution. But aromatic rings like to remain aromatic. stability of that carbocation is crucial to the reaction. but some basics are called for here.Resonance Effects Let's first look at resonance effects. This is the case in Electrophilic Aromatic Subsitution as well. abstracting it from the ring and allowing the pi-bond to re-form and returning the ring to its aromatic nature. This in turn creates a carbocation on the adjacent carbon. The nucleophile which was previously bonded to the electrophile now attacks the hydrogen. As you can see in the image above. The same carbon is now bonded to both the hydrogen that was bonded to it and the electrophile. So what is the effect of substituents on the ring? 61 . To see this. making the ring non-aromatic.

There are 3 possible places for the nitro group to attach: An ortho. In the para attack situation. The first resonance structure of the ortho attack results in a positive charge on the carbon with the hydroxyl group. a benzene ring with an -OH (hydroxyl) group attached. When we nitrate the ring with nitric acid in sulfuric acid (a reaction we'll discuss in the next section). we need to look at the resonance structures for a given attack and see what the results are. Hydrogen can do nothing to stabilize the charge and thus. The other two resonance forms leave a carbon with a hydrogen attached. So the electron pairs in the oxygen act to stabilize the ortho and para attacks. In this case we have Phenol. 62 . is a very small percentage of the product. This provides for stability just as it does in the case of an ortho attack and thus. To understand the stability of the carbocation. meta attack with a hydroxyl group attached. a nitro group is attached to the benzene ring. all of the resonance forms result in a positive charge on a carbon with only a hydrogen attached.Let's look at the situation above. or para position. the middle resonance form is very stable. This happens to be the most stable of the 3 resonance structures for an ortho attack because the two negative electron pairs in the oxygen act to stabilize the positive charge on the carbon. in the meta attack situation. meta. and thus. None of these is stable. notice that the second resonance form also puts a positive charge on the carbon with the hydroxyl group. Finally. to hold the positive charge. these are less stable forms.

strongly deactivating its pi-bond nature and putting a positive dipole on the carbon. making the resonance structures with ortho and para attacks relatively more stable than the meta attack resonance forms. are meta directing. Though nitrogen is more electronegative than carbon. Let's imagine that. but let's look more closely at the substituents and try to understand the details of what makes them activating vs. but the inductive effect of the doublebonded oxygen acts to make the nitrogen more electron withdrawing. meta is the preferred position. There's no negative charge or negative electron pair to stabilize this positive charge. Positive plus positive equals more positive and thus. But halides also have a bunch of electrons in their outer shell to share with the ring. but less so. instead of a hydroxyl group. Halides as the Exception Notice that in the list of activating vs. deactivating substituents. When a carbonyl is attached. -OH and -O. the doublebonded oxygen is withdrawing electrons and this inductive effect is felt on the ring. This means that. less stable. In the deactivating substituents. -OCH3 and -OR are also still strongly activating. -NH2.Inductive Effects Now let's look at the inductive effects of deactivating substituents. and -NRR are all very strongly activating. they are still ortho/para directing. Why are halides an exception? Halides are more electronegative than carbon and thus they put a positive dipole on the carbon they're attached to and thus deactivate the ring. this carbon. is double-bonded to an oxygen. in the case of ortho and para attacks. So in this case. but the ortho and para attacks result in much more unstable carbocation resonance forms. Thus their effect is only weakly felt. the ring is bonded to a carbon which in turn. Detailed Effects of Substituents We've discussed some generalities about the effects of substituents and even some specifics about certain ones. but not nearly as much as a pair of electrons.is similar in that it is even more electronegative than nitrogen. all but the halides. its ability to share a pair of electrons greatly outweighs its electron withdrawing effect. which already has some positive nature is now given the added resonance of a positive charge. but the overall reaction is less active than plain benzene. but it has two pairs of electrons to share. Looking at the resonance structures. not only is the entire ring less activated. -NHCOCH3 and -NHCOR are also strongly activating. which also greatly outweighs its electon withdrawing effect. For deactivating groups we have: 63 . -CH3 and -R in general provide some electron density sharing. the activating ones are all ortho/para directing. though halides do deactivate the ring to some extent. Hence. we instead have a carbonyl group attached to the ring in its place. -NHR. because the electron density is shared on both sides of the oxygen. so they're not quite as activating as the other -N subsituents above. deactivating.

In order for benzene to react in most situations. it gains or loses some functionality dependent on which functional groups are attached. all have a similar effect. making it harder for it to share its electrons. but with no electrons to share with the ring. more complicated molecules. allowing the ortho/para direction. -CF3 and -CCl3 both have an inductive electronegative effect of 3 halides. -SO3. meaning that between the electronegativity of the nitrogen and positively charged carbon in the resonance form. leaving them also very strongly deactivating. it destabilizes the carbocation and offer no electrons to the ring. -CN has a triple bond between the carbon and nitrogen with a resonance form of a double bond between the carbon and nitrogen and a positive charge on the carbon. Where each group attaches is most often a function of which order they were attached in. Although the simplest case is to work with benzene that has only one functional group. which is why the arene substitution patterns ortho.and O--N+=O. But to understand their effects better. The same applies to -NR3+. For example three isomers exist for the molecule cresol because the methyl group and the hydroxyl group can be placed either next to each other (ortho). -Br. due to the activating/deactivating and directing activities of previously attached groups. When there is more than one substituent present on a benzene ring the spatial relationship betwen groups becomes important. Florine is the most electronegative element and it's very small and thus very close to the hydrogen it's bonded to. They are electronegative and deactivate the ring. you need to look at them in terms of their placement on the periodic chart. Polysubstituted Benzenes Unsubstituted benzene is seldom encountered in nature or in the laboratory.-NO2. or nitro and -NR3+. -Cl.all of these have electronegative oxygens giving the carbon a positive partial charge and providing no electrons for stability on the ring. and you will find in your studies that most often benzene rings are found as parts of other. it is also essential to understand the interactions and competitions between multiple functional groups attached to the same benzene ring. And so on. to some degree. The nitro group is very strongly deactivating because of its resonance structure. one position removed from each other (meta) or two positions removed from each other (para). This gives its electromagnetic influence a stronger deactivating character. -F. meta and para were devised. but have electrons to share that. Chlorine is less electronegative. The nitro group has two resonance forms: O=N+-O. -COR. Both of these forms leave a full positive charge on the nitrogen making it completely unable to help stabilize the positive carbocation intermediate. 64 . but it's also larger and thus further away from the carbon. makes up for it. -CO2R .

The positions meta to the nitro are also ortho to the methyl. followed by a hyphen and the group's name. most of your product would tend to be ortho/para to the toluene and not meta to the nitro. RCHXCH2X + Zn H2O d.Competition Between Functional Groups When a ring has more than one functional group. the more activating group is the one that controls direction. despite the nitro having a stronger influence on overall activation. i. toluene (methylbenzene) is weakly activated. if you had m-nitrotoluene. That is. "2-methyl-5-nitrobenzaldehyde. But p-nitrotoluene has both a methyl group and a nitro group. so this works out and further substituents will be almost entirely in the positions ortho to the methyl group. The methyl group is ortho/para directing. Sintesa alkena H2O a. so the methyl will now want just ortho direction. The nitro group occupies the para position. which itself would take precedence over an alcohol or alkane group.. If two functional groups disagree on direction. so overall. This is done by listing the number of the carbon atom where the group is attached. effects are summed." . The methyl group is weakly activating and the nitro is pretty strongly deactivating. RCH2CH2X + KOH b. RCHOH-CH3 + H2SO4 c. i. The names of the groups should be listed in alphabetical order. the location of all of the groups not directly attached to carbon number one must be explicitly declared. Naming Conventions When a benzene ring has more than one substituent group attached. In terms of direction. In general. The carbon atoms of the benzene ring should be numbered in order of previously established precedence. R-CH = CH2 + Hg(OCOCH3)2 25 oC RCH=CH2+ KX + H2O RCH=CH2 + H2O RCH=CH2 + ZnX2 R-CH = CH3 OH R-CH = CH2 + NaBH4 OH HgOCOCH3 Alkuna Pemberian nama alkuna berdasarkan nama homolog alkana dimana akhiran ana diganti dengan una. the effects of the groups are combined and their total effect must be taken into account. however. the group is very deactivated.e. both substitutents agree on the direction. Contohnya HC CH etuna Alkuna alifatik 65 .e. For example. a bromine would take precedence over a nitro group. The nitro group is meta directing.

RC Senyawa CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 C3000H6002 Nama Metuna Etuna Propuna Butuna Pentana Heksuna Heptuna Oktuna Nonuna Dekuna Undekuna Dodekuna Tridekuna Tetradekuna Pentadekuna Heksadekuna Heptadekuna Oktadekuna Nonadekuna Eikosuna Heneikosuna Dokosuna Trikosuna Tetrakosuna Pentakosuna Heksakosuna Heptakosuna Oktakosuna Nonakosuna Triakontuna Hentriakontuna Dotriakontuna Tritriakontuna Hektuna Diktuna Triktuna kiliuna Diliuna Triliuna Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 C41H58 C42H60 C43H62 C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C4000H8002 C500H10002 C3000H6002 CH Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 C74H150 C75H152 C76H154 C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C7000H14002 C8000H16002 C9000H18002 Nama heptaHeksa kontuna oktaHeksa kontuna nonaHeksa kontuna Heptakontuna henHeptakontuna DoHeptakontuna triHeptakontana tetraHeptakontuna pentaHeptakontuna heksaHeptakontana heptaHeptakontuna oktaHeptakontuna nonaHeptakontuna Oktakontuna henOktakontuna doOktakontuna triOktakontuna tetraOktakontuna pentaOktakontuna heksaOktakontuna heptaOktakontuna oktaOktakontuna nonaOktakontuna Nonakontuna henNonakontuna doNonakontuna triNonakontuna tetraNonakontuna pentaNonakontuna heksaNonakontuna HeptaNonakontuna oktaNonakontuna nonaNonakontuna Heptaktuna Oktaktuna Nonaktuna Heptaliuna Oktaliuna Nonaliuna Nama tetratriakontuna pentatriakontuna heksatriakontuna heptatriakontuna oktatriakontuna nonatriakontuna Tetrakontuna hentetrakontuna Dotetrakontuna Tritetrakontuna tetratetrakontuna pentatetrakontuna heksatetrakontuna heptatetrakontuna oktatetrakontuna nonatetrakontuna Pentakontuna Henpentakontuna dopentakontuna tripentakontuna tetrapentakontuna pentapentakontuna heksapentakontuna heptapentakontuna Oktapentakontuna nonapentakontuna Heksa kontana HenHeksa kontuna doHeksa kontuna triHeksa kontuna tetraHeksa kontuna pentaHeksa kontuna heksaHeksa kontuna Tetraktuna Pentaktuna Heksaktuna Tetraliuna Pentaliuna Heksaliuna Alkapoliuna R(C CH)n Contohnya : HC CH-HC CH Butadiuna Sintesa Alkuna 66 .

54 and 1. sharing three electron pairs between carbons instead of just two. CH4 + 3H2 b. is a bond in which the carbon atoms share an s and two p orbitals to form just one σ and two π bonds between them. What this does is create the appearance of only being bound to three other atoms. carbon is generally found in a tetravalent state . then.a triple bond. Multiple Bonds Between Carbon Atoms As you know from studying alkenes.sintesa alkuna dalam Industri a. The simplest alkyne is ethyne (HCCH). but in actuality four bonds exist. the alkyne has at least one pair of carbon atoms who have a σ and two π bonds -. They exhibit neither geometric nor optical isomerism. but instead of forming a double bond with only one sigma (σ) and one pi (π) bond. The carbon-carbon triple bond. because carbon atoms can double-bond to one another. 67 . the case.20Ǎ. Alkynes take this sharing a step further than alkenes. commonly known as acetylene. Two π Bonds As you should know already. it would be logical to predict that the triple bond would be shorter still. which consists of one sigma (σ) and one pi (π) bond. RCHXCH2X + KNH2 e. all four bonds are not necessarily to different atoms. is shorter than that of ethane and ethene’s 1.it forms four covalent bonds with other atoms. respectively. Alkynes are also molecules consisting of carbon and hydrogen atoms. atoms do not always bond with only one pair of electrons. Since we know that double bonds are shorter than single covalent bonds. and this is. As you know from the section on alkenes. The triple bond’s length. as shown at right. thus allowing carbon bonds to become stronger. but the difference between the triple and double bonds is slightly less than the difference between the single and double bonds. CH4 + O2 c. 1. due to the nucleus central force which pulls in nearby atoms << Alkenes |Alkynes| Dienes >> Alkynes are hydrocarbons containing carbon-carbon triple bond. due to the absence of hydrogens. RCX2CH2X + Zn R-C CH R-C CH The triple carbon bonds is formed in alkenes.34 angstroms. In alkenes (as well in other organic and inorganic molecules) pairs of atoms can share between themselves more than just a single pair of electrons. This results in a linear molecule with a bond angle of about 180 ゚. in fact. Alkenes are molecules that consist of carbon and hydrogen atoms where one or more pairs of carbon atoms participate in a double bond. CaC2 + H2O HC CH HC CH HC CH + Ca(OH)2 Sintesa alkuna di laboratorium d.

Every π-bond in the molecule increases the index by one.The chemistry is very similar to alkenes in that both are formed by elimination reactions. Here is a list of possibilities: Per molecule One double bond 1 ring 1 double bond and 1 ring 2 double bonds 1 triple bond 1 triple bond + 1 double bond 3 double bonds 2 double bonds + 1 ring 2 triple bonds 4 double bonds Index of Hydrogen Deficiency 1 1 2 2 2 3 3 3 4 4 Just remember that double bonds have 1 π bond. Identify the Alkane molecular formula for six carbons. and the major chemical reactions that alkynes undergo are addition type reactions. and Alkyne families as well as the Cycloalkane and cycloalkene families we see the following relationship: Family Alkane Alkene Alkyne Molecular Formula CnH2n+2 CnH2n CnH2n-2 Cycloalkane CnH2n Cycloalkene CnH2n-2 We see that for a ring structure or a double bond there is a difference of two hydrogens compared to the alkane structure with the same number of carbons. triple bonds have 2 π bonds and each π bond is an index of 1. Index Of Hydrogen Deficiency If we compare the general molecular formulas for the Alkane. Any ring structure increases the index by one. For n = 6 we would have CnH2n+2. That would be C6H14. Alkene. We say that the Index of Hydrogen Deficiency is equal to the number of pairs of Hydrogens that must be taken away from the alkane to get the same molecular formula of the compound under investigation. For example. determine the molecular formula and speculate on what kind of Pi bonding and/or ring structure the molecules would have if the Index was given to be 3 and it is a 6 carbon hydrocarbon. If there is a ring + double bond (cycloalkene) or a triple bond (alkyne) then the difference is four hydrogens compared to the alkane with the same number of carbons. We can use the index and the molecular formula to identify possibilities as to the exact nature of the molecule. 68 .

In speculating as to what the bonding and structure could be with an index of 3 that could mean: • o o o Three double bonds in a non-cyclic structure like hexatriene Two double bonds in a ring structure like a cyclohexadiene One triple bond and one double bond in a non-cyclic structure Clearly the answer cannot be determined from the formula alone.-> 2Na 2Na + H20 -> 2NaOH + H2 69 . Cyclononyne is the smallest stable cycloalkyne. and will polymerize with itself quickly. This is called a double dehydrohalogenation. resulting in a carbon-carbon triple bond due to the loss of both halogens as well as two hydrogen atoms from the starting molecule. One such compound is maleic acid. Mechanism is similar to that of formation of ethane using kolbe's electrolysis. Adding sodium amide (NaNH2) removes the halogens with regiochemistry subject to Zaitsev's Rule. and are not stable in small rings due to angle strain. The starting compound is a salt already containing a carbon-carbon double bond. Benzyne is another cycloalkyne that has been proposed as an intermediate for elimination-addition reactions of benzene. but the formula will give important clues as to a molecule's structure. Preparation In order to synthesize alkynes. one generally starts with a vicinal or geminal dihalide (an alkane with two halogen atoms attached either next to one another or across from one another). but is very reactive. Cyclooctyne has been isolated.-> CH-COO* || -> -2CO2 CH-COO* (free radical formation) -> CH* || CH* -> CH ||| CH (sodium maleate) (maleic acid) At cathode: 2Na+ + 2e. then we would have C6H14-6 or C6H8. Cycloalkynes Cycloalkynes are seldom encountered.Since an index of 3 means that there are 3 pairs(2) of hydrogen atoms less in the compound compared with the alkane we determined in step 1. CH-COONa | CH-COONa At Anode: CH-COO|| CH-COO-2e.

One synthetically important property of terminal alkynes is the acidity of their protons. Instant hydrolysis occurs when water is added to calcium carbide. The acidity of alkynes allows them easily to be deprotonated by sufficiently strong bases. alkyne is obtained at anode. an extremely weak acid (though not as weak as ammonia). as a result of the electron density near the triple bond. while NaOH is formed at cathode and hydrogen gas is liberated. but there are a few exceptions. From Calcium carbide Calcium carbide is the compound CaC2. 70 . For this reason it is produced in an electrical arc furnace. yielding acetylene gas. PhCCH has a pKa around 23. Substitution of the alkyne can reduce the pKa of the alkyne even further. immiscible with water. terminal alkynes have pKa's of about 25. such as butyllithium BuLi or the amide ion NH2-. C22-. Alkynes with a low ratio of hydrogen atoms to carbon atoms are highly combustible. Vicinal dihalides may be converted into alkynes by using extreme conditions such as sodium amide NaNH2 typically at 150°C or molten/fused potassium hydroxide KOH typically at 200°C. From alkyl or aryl halides Properties Physical properties Most alkynes are less dense than water (they float on top of water). Alkynes are. Chemical properties Liquid alkynes are non-polar solvents. Triple bonds store large amounts of chemical energy and thus are highly exothermic when broken.In this manner. More acidic alkynes such as PhCCH can even be deprotonated by alkoxide bases under the right conditions. and Me3SiCCH has a pKa around 19. The heat released can cause rapid expansion. which consists of calcium ions (Ca2+) and acetylide ions. more polar than alkanes or alkenes. Carboncarbon triple bonds are highly reactive and easily broken or converted to double or single bonds. Calcium carbide may formally be considered a derivative of acetylene. It is synthesized from lime and coke in the following reaction: CaO + 3C → CaC2 + CO This reaction is very endothermic and requires a temperature of 2000o C. for example. The double deprotonation means that the carbide ion has very high energy. so care must be taken when working with alkynes such as acetylene. however. Whereas the protons in alkanes have pKa's around 60 and alkene protons have pKa's in the mid-40's.

Rh.2-dihaloalkene. Complete Hydrogenation of Alkynes As mentioned above. the alkyne hydrogenates to a Z enantiomer alkene. Hydrohalogenation of Alkynes Alkynes react very quickly and to completion with hydrogen halides. for example. such as Pt. yellow flame. If Lindlar's catalyst is used instead. if the halogen is added in excess. an E enantiomer alkene is the result. alkynes are reduced to alkanes in the presence of an active metal catalyst. Combustion Alkynes burn in air with a sooty.2. or. like alkanes. a 1. Halogenation of Alkynes Adding diatomic halogen molecules such as Br2 or Cl2 results in 1. such as palladium-carbon or platinum or nickel. 71 . Addition is anti.2-tetrahaloalkane. but adding HBr in the presence of peroxides results in the Anti-Markovnikov alkenyl bromide product. Alkenes also burn yellow. while alkanes burn with blue flames. and follows the Markovnikov Rule.1. and is used in oxyacetylene torches for welding metals together. or Ni in the presence of heat and pressure. Acetylene burns with large amounts of heat. whereas the anti-Markovnikov aldehyde product requires different reagents and is a multi-step process. Pd. in the superstructures of skyscrapers. 2 C2H2 + 5 O2 --> 4 CO2 + 2 H2O Reduction Alkynes can be hydrogenated by adding H2 with a metallic catalyst. which results in a both of the alkyne carbons becoming fully saturated. and if an alkali metal in an ammonia solution is used for hydrogenating the alkyne.Reactions Alkynes can be hydrated into either a ketone or an aldehyde form. RCCH + H-Br (1 equiv) --> RCBr=CH2 RCCH + H-Br (2 equivs) --> RCBr2CH3 Adding a halide acid such as HCl or HBr to an alkyne can create a geminal dihalide via a Markovnikov process. A (Markovnikov) ketone can be created from an alkyne using a solution of aqueous sulfuric acid (H2O/H2SO4) and HgSO4. Adding H2O along with the diatomic halide results in a halohydrin addition and an α-halo ketone.

72 .RCCR' + 2 H2 (Pt cat. palladium doped with CaSO4 or BaSO4. They react by nucleophilic substitution with alkyl halides. RCCR + H2 cis-RCH=CHR Anti-Hydrogenation of an Alkyne In regards to the syn-hydrogenation. and acetylene (ethyne) is produced in a science classroom reaction of calcium carbide with water. Isotopic identification allows chemists to determine when this syn-hydrogenation has occurred. As mentioned above. i. CaC2 + 2 H20 --> Ca(OH)2 + C2H2 Alkynyl anions are useful in lengthening carbon chains. R-Cl + R'CCNa --> RCCR' + NaCl The product of this reaction can be reduced to an alkane with hydrogen and a platinum or rhodium catalyst.)--> RCH2CH2R' Syn-Hydrogenation of an Alkyne There are two kinds of addition type reactions where a π-bond is broken and atoms are added to the molecule. or an alkene with Lindlar palladium. they are easily converted into alkynyl anions in high yield by strong bases. anti is hydrogenation when one hydrogen is added from the top of the pi bond and the other is added from the bottom. Hydrogen atoms can be added to an alkyne on a one mole to one mole ratio to get an alkene where the hydrogen atoms have been added on the same side of the molecule. If the added atoms are added on opposite sides of the molecule then the addition is said to be an "anti" addition. Anion formation Because of the acidity of the protons of terminal alkynes. Examples RCCH + NaNH2 -> RCCNa + NH3 C4H9Li + RCCH -> C4H10 +RCCLi Alkynes are stronger bases than water. If the atoms are added on the same side of the molecule then the addition is said to be a "syn" addition. alkynes can be reduced to cis-alkenes by hydrogen in the presence of Lindlar Pd.e.

4. For example. Pemberian nama alkyl halida Senyawa CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 Nama Metil halida Etil halida Propil halida Butil halida Pentil halida Heksil halida Heptil halide Oktil halide Nonil halide Dekil halide Undekil halide Dodekil halide Tridekil halide Tetradekil halide Pentadekil halide Heksadekil halide Heptadekil halide Oktadekil halide Nonadekil halide Eikosil halide Heneikosil halide Dokosil halide Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 C41H58 C42H60 C43H62 C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 Nama Tetratriakontil halida Pentatriakontil halida Heksatriakontil halide Heptatriakontil halide Oktatriakontil halida Nonatriakontil halida Tetrakontil halida Hentetrakontil halida Dotetrakontil halide Tritetrakontil halida Tetratetrakontil halida Pentatetrakontil halida Heksatetrakontil halida Heptatetrakontil halida Oktatetrakontil halida Nonatetrakontil halide Pentakontil halide Henpentakontil halide Dopentakontil halide Tripentakontil halide Tetrapentakontil halide Pentapentakontil Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 C74H150 C75H152 C76H154 C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 Nama heptaHeksa kontil halida oktaHeksa kontil halida nonaHeksa kontana Heptakontil halida henHeptakontil halide DoHeptakontil halide triHeptakontil halide tetraHeptakontil halide pentaHeptakontil halide heksaHeptakontil halide heptaHeptakontil halide oktaHeptakontil halide nonaHeptakontil halide Oktakontil halide henOktakontil halide doOktakontil halida triOktakontil halide tetraOktakontil halide pentaOktakontil halide heksaOktakontil halide heptaOktakontil halide oktaOktakontil halide 73 . iodo-.. Multiple groups are dichloro-. depending on the halogen.1trifluoroethane. chloro-. etc. and dissimilar groups are ordered alphabetically as before. bromo-.1.Alkil halide Halogens (Alkyl Halides) Main article: Halogens Halogen functional groups are prefixed with the bonding position and take the form fluoro-. CHCl3 (chloroform) is trichloromethane. 5. trichloro-. etc. The anesthetic Halothane (CF3CHBrCl) is 2-bromo-2-chloro-1.1.

4. R-CH2CH2OH + HX e.2. R-CH2CH2OH + PX3 g. R-CH2CH2OH + NaX + H2SO4 d.4.2. Sintesa alkil halida a. C6H5CH3 + X2 b. RHC=CH2 + HX 5. R-CH2CH2OH + SOX2 f. (CH3)3CCH3 + X2 C6H5CH2X + HX (CH3)3CCH2X + HX R-CH2CH2X + Na2SO4 + H2O c. Reaksi-reaksi alkil halide R-CH2CH2X + H2O R-CH2CH2X + H2SO4 R-CH2CH2X + H3PO4 R-CH2CH2X Alkanol 74 .C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 C3000H6002 Trikosil halide Tetrakosil halide Pentakosil halide Heksakosil halide Heptakosil halide Oktakosil halide Nonakosil halide Triakontil halide Hentriakontil halide Dotriakontil halide Tritriakontil halida Hektil halida Dohektil halide Trihektil halide Kiliil halide Diliil halide Triliil halida C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C500H10002 C600H1202 halida Heksapentakontil halida Heptapentakontil halida Oktapentakontil halida Nonapentakontil halida Heksa kontil halide HenHeksa kontil halide doHeksa kontil halide triHeksa kontil halide tetraHeksa kontil halide pentaHeksa kontil halide heksaHeksa kontil Tetrahektil halide Pentahektil halide Heksahektil halide Tetraliil halide Penliil halide Heksaliil halide C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C700H14002 C800H16002 C900H18002 nonaOktakontil halide Nonakontil halide henNonakontil halide doNonakontil halide triNonakontil halide tetraNonakontil halide pentaNonakontil halide heksaNonakontil halide HeptaNonakontil halide oktaNonakontil halide nonaNonakontil halide Heptahektil halide Oktahektil halide Nonahektil halide Heptaliil halide Oktaliil halide Nonaliil halide 5.

The suffixes -diol.2-diol. etc. Pemberian nama deret homolog alkanol Senyawa CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 Nama Metanol Etanol Propanol Butanol Pentanol Heksanol Heptanol Oktanol Nonanol Dekanol Undekanol Dodekanol Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 C41H58 C42H60 C43H62 C44H64 C45H66 Nama Tetratriakontanol Pentatriakontanol Heksatriakontanol Heptatriakontanol Oktatriakontanol Nonatriakontanol Tetrakontanol Hentetrakontanol Dotetrakontanol Tritetrakontanol Tetratetrakontanol Pentatetrakontanol Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 C74H150 C75H152 C76H154 C77H156 C78H158 Nama heptaHeksa kontanol oktaHeksa kontanol nonaHeksa kontanol Heptakontanol henHeptakontanol DoHeptakontanol triHeptakontanol tetraHeptakontanol pentaHeptakontanol heksaHeptakontanol heptaHeptakontanol oktaHeptakontanol 75 . etc.Alcohols (R-OH) take the suffix "-ol" with an infix numerical bonding position: CH3CH2CH2OH is propan-1-ol. below). are used for multiple -OH groups: Ethylene glycol CH2OHCH2OH is ethane-1.. If higher precedence functional groups are present (see order of precedence. Alcohols (R-OH) take the suffix "-ol" with an infix numerical bonding position: CH3CH2CH2OH is propan-1-ol. The suffixes -diol. the prefix "hydroxy" is used with the bonding position: CH3CHOHCOOH is 2-hydroxypropanoic acid. -triol.2-diol.. If higher precedence functional groups are present (see order of precedence. -tetraol. -tetraol. are used for multiple -OH groups: Ethylene glycol CH2OHCH2OH is ethane-1. the prefix "hydroxy" is used with the bonding position: CH3CHOHCOOH is 2hydroxypropanoic acid. -triol. below).

RMgX + R-C= O g. R-CH = CH2 + B2H6 (RCH2– CH2)3-B+ H2O2 OH H2O - RCH2– CH2OH d. R-CH = CH2 + Hg(OCOCH3)2 H e.C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 C3000H6002 Tridekanol Tetradekanol Pentadekanol Heksadekanol Heptadekanol Oktadekanol Nonadekanol Eikosanol Heneikosanol Dokosanol Trikosanol Tetrakosanol Pentakosanol Heksakosanol Heptakosanol Oktakosanol Nonakosanol Triakontanol Hentriakontanol Dotriakontanol Tritriakontanol Hektanol Dohektanol Trihektanol Kilianol Dilianatanol Trilianol C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C500H10002 C600H1202 Heksatetrakontanol Heptatetrakontanol Oktatetrakontanol Nonatetrakontanol Pentakontanol Henpentakontanol Dopentakontanol Tripentakontanol Tetrapentakontanol Pentapentakontanol Heksapentakontanol Heptapentakontanol Oktapentakontanol Nonapentakontanol Heksa kontanol HenHeksa kontanol doHeksa kontanol triHeksa kontanol tetraHeksa kontanol pentaHeksa kontanol heksaHeksa kontanol Tetrahektanol Pentahektanol Heksahektanol Tetralianol Pentaliaanol Heksalianol C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C700H14002 C800H16002 C900H18002 nonaHeptakontanol Oktakontanol henOktakontanol doOktakontanol triOktakontanol tetraOktakontanol pentaOktakontanol heksaOktakontanol heptaOktakontanol oktaOktakontanol nonaOktakontanol Nonakontanol henNonakontanol doNonakontanol triNonakontanol tetraNonakontanol pentaNonakontanol heksaNonakontanol HeptaNonakontanol oktaNonakontanol nonaNonakontanol Heptahektanol Oktahektanol Nonahektanol Heptalianol Oktalianol Nonalianol Sintesa alkanol a.CH2 + NaBH4 R-CH-CH3 25 oC OH HgOCOCH3 OH R R RCHOMgX + H2O RCHOH + MgXOH RCH2OH 76 . RX + OHb. LiAlH4 + RCHO Reaksi-reaksi alkanol Alkoksi alkana Main article: Ethers R-CH . C = C + H2O ROH + XCH – COH c.

The shorter of the two chains becomes the first part of the name with the -ane suffix changed to -oxy. Thus CH3OCH3 is methoxymethane. and the longer alkane chain become the suffix of the name of the ether. Thus CH3OCH(CH3)2 is 2-methoxypropane. then the whole shorter alkyl-plus-ether group is treated as a side-chain and prefixed with its bonding position on the main chain. Senyawa CH3OC2H5OC3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 Nama Metoksi Etoksi Propoksi Butoksi Pentoksi Heksoksi Heptoksi Oktoksi Nonoksi Dekoksi Undekoksi Dodekoksi Tridekoksi Tetradekoksi Pentadekoksi Heksadekoksi Heptadekoksi Oktadekoksi Nonadekoksi Eikosoksi Heneikosoksi Dokosoksi Trikosoksi Tetrakosoksi Pentakosoksi Heksakosoksi Heptakosoksi Oktakosoksi Nonakosoksi Triakontoksi Hentriakontoksi Dotriakontoksi Tritriakontoksi Hektoksi Dohektoksi Trihektoksi Kilioksi Dilioksi Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 C41H58 C42H60 C43H62 C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C500H10002 Nama tetratriakontoksi pentatriakontoksi heksatriakontoksi heptatriakontoksi oktatriakontoksi nonatriakontoksi Tetrakontoksi hentetrakontoksi Dotetrakontoksi Tritetrakontoksi tetratetrakontoksi pentatetrakontoksi heksatetrakontoksi heptatetrakontoksi oktatetrakontoksi nonatetrakontoksi Pentakontoksi Henpentakontoksi Dopentakontoksi Tripentakontoksi Tetrapentakontoksi Pentapentakontoksi Heksapentakontoksi Heptapentakontoksi Oktapentakontoksi Nonapentakontoksi Heksa kontoksi HenHeksa kontoksi doHeksa kontoksi triHeksa kontoksi tetraHeksa kontoksi pentaHeksa kontoksi heksaHeksa kontoksi Tetrahektosi Pentahektoksi Heksahektosi Tetralioksi Penlioksi Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 C74H150 C75H152 C76H154 C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C700H14002 C800H16002 Nama heptaHeksa kontoksi oktaHeksa kontoksi nonaHeksa kontoksi Heptakontoksi henHeptakontoksi DoHeptakontoksi triHeptakontoksi tetraHeptakontoksi pentaHeptakontoksi heksaHeptakontoksi heptaHeptakontoksi oktaHeptakontoksi nonaHeptakontoksi Oktakontoksi henOktakontoksi doOktakontoksi triOktakontoksi tetraOktakontoksi pentaOktakontoksi heksaOktakontoksi heptaOktakontosi oktaOktakontoksi nonaOktakontoksi Nonakontoksi henNonakontoksi doNonakontoksi triNonakontoksi tetraNonakontoksi pentaNonakontoksi heksaNonakontoksi HeptaNonakontoksi oktaNonakontoksi nonaNonakontoksi Heptahektoksi Oktahektoksi Nonahektoksi Heptaliokai Oktalioksi 77 .Ethers (R-O-R) consist of an oxygen atom between the two attached carbon chains. and CH3OCH2CH3 is methoxyethane (not ethoxymethane). If the oxygen is not attached to the end of the main alkane chain.

CH2 + NaBH4 OR HgOCOCF3 R-O-R’ + NaCl H3C-CH2-O-H2C-CH3 . C7H13OH + CH2N2 e. H3C-CH2OH + H2SO4 b. Contoh H3C-CH2-CH2-O-CH2-CH3 Etoksi propana Sintesa alkoksi alkana a. (H3C)2-CH-O-CH-(H3C)2 Alkanal Main article: Aldehydes 78 . C6H5OH + CH2N2 f. R-O-Na + R’Cl BF3 d. (H3C)2-CHCl + Ag2O c.C3000H6002 Trilioksi C600H1202 Heksalioksi C900H18002 Nonalioksi Pemberian nama Nama senyawa alkoksi alkana adalah nama homolog alkana. dimana nama alkana sebelum atom oksigen akhiran nama alkana diganti dengan akhiran oksi dan nama homolog alkana sesudah atom oksigen sesuai dengan homolog alkananya. R-CH = CH2 + Hg(OCOCF3)2 + R’OH C7H13OCH3 + N2 C6H5OCH3 + N2 R-CH .

If a prefix form is required.1. If a aldehyde is attached to a benzene and is the main functional group. the prefix "formyl-" or the suffix "-carbaldehyde" is used: C6H11CHO is cyclohexanecarbaldehyde. the suffix becomes benzaldehyde. Pemberian nama alkanal Nama alkanal berasal dari homolog alkana dengan mengganti akhiran a dengan al Senyawa CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 Nama Metanal Etanal Propanal Butanal Pentanal Heksanal Heptanal Oktanal Nonanal Dekanal Undekanal Dodekanal Tridekanal Tetradekanal Pentadekanal Heksadekanal Heptadekanal Oktadekanal Nonadekanal Eikosanal Heneikosanal Dokosanal Trikosanal Tetrakosanal Pentakosanal Heksakosanal Heptakosanal Oktakosanal Nonakosanal Triakontanal Hentriakontanal Dotriakontanal Tritriakontanal Hektanal Dohektanal Trihektanal Kilianal Dilianatanal Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 C41H58 C42H60 C43H62 C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C500H10002 Nama Tetratriakontanal Pentatriakontanal Heksatriakontanal Heptatriakontanal Oktatriakontanal Nonatriakontanal Tetrakontanal Hentetrakontanal Dotetrakontanal Tritetrakontanal Tetratetrakontanal Pentatetrakontanal Heksatetrakontanal Heptatetrakontanal Oktatetrakontanal Nonatetrakontanal Pentakontanal Henpentakontanal Dopentakontanal Tripentakontanal Tetrapentakontanal pentapentakontanal Heksapentakontanal Heptapentakontanal Oktapentakontanal Nonapentakontanal Heksa kontanal HenHeksa kontanal doHeksa kontanal triHeksa kontanal tetraHeksa kontanal pentaHeksa kontana heksaHeksa kontanal Tetrahektanal Pentahektanal Heksahektanal Tetralianal Penliaanal Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 C74H150 C75H152 C76H154 C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C700H14002 C800H16002 Nama heptaHeksa kontanal oktaHeksa kontanal nonaHeksa kontanal Heptakontanal henHeptakontanal DoHeptakontanal triHeptakontanal tetraHeptakontanal pentaHeptakontanal heksaHeptakontanal heptaHeptakontanal oktaHeptakontanal nonaHeptakontanal Oktakontanal henOktakontanal doOktakontanal triOktakontanal tetraOktakontanal pentaOktakontanal heksaOktakontanal heptaOktakontanal oktaOktakontanal nonaOktakontanal Nonakontanal henNonakontanal doNonakontanal triNonakontanal tetraNonakontanal pentaNonakontanal heksaNonakontanal HeptaNonakontanal oktaNonakontanal nonaNonakontanal Heptahektanal Oktahektanal Nonahektanal Heptalianal Oktalianal 79 .If other functional groups are present. 5. with the position number indicating the end of a chain: CHOCH2COOH is 3-oxopropanoic acid. the chain is numbered such that the aldehyde carbon is in the "1" position.Aldehydes (R-CHO) take the suffix "-al". "oxo-" is used (as for ketones). If the carbon in the carbonyl group cannot be included in the attached chain (for instance in the case of cyclic aldehydes).7.

3.(CH2)5 C =O + H3C-S-CH3 H + H2O ArCHO R-CHO + LiCl + p-(CH3)2CHC6H4CHO CuCl 5. H3C-(CH2)6I + CH3 . RCH2OH + KMnO4 O b. AlCl3 e. Propanon Butanon Pentanon Heksanon Heptanon Oktanon Nonanon Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 C41H58 C42H60 Nama Tetratriakontanon Pentatriakontanon heksatriakontanon Heptatriakontanon Oktatriakontanon Nonatriakontanon Tetrakontanon Hentetrakontanon Dotetrakontanon Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 C74H150 C75H152 Nama heptaHeksa kontanon oktaHeksa kontanon nonaHeksa kontanon Heptakontanon henHeptakontanon DoHeptakontanon triHeptakontanon tetraHeptakontanon pentaHeptakontanon 80 .C3000H6002 Trilianal C600H1202 Heksalianal C900H18002 Nonalianal 5.7.2. RCOCl + LiAl{(CH3)3CO}3)2H HCl..7. Reaksi-reaksi alkanal Alkanon Main article: Ketones Al{(CH3)3CO}3)2 d. the prefix "oxo-" is used: CH3CH2CH2COCH2CHO is 3-oxohexanal. Ar-CH3 + Cl2 Ar-CH-Cl2 RC =O H H3C. if a higher precedence suffix is in use. Pemberian nama alkanon Nama alkanon berasal dari homolog alkana dengan mengganti akhiran a dengan on Senyawa CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 Nama Metan……. Sintesa alkanal a. not won) with an infix position number: CH3CH2CH2COCH3 is pentan-2-one.CH3 c. C6H5(CH3)2 + CO In general ketones (R-CO-R) take the suffix "-one" (pronounced own. Etan…….S .

R-CClCH = O + H2C=CHR R O (R-C-CH2– CHCl) + RCCH=CHR 81 . R2CHOH + KMnO4 + 8 H+ R2C=O + Mn+2 + 4H2O + K+ AlCl3 b ArH + RCOCl ArCOR + HCl O c.C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 C3000H6002 Dekanon Undekanon Dodekanon Tridekanon Tetradekanon Pentadekanon Heksadekanon Heptadekanon Oktadekanon Nonadekanon Eikosanon Heneikosanon Dokosanon Trikosanon Tetrakosanon Pentakosanon Heksakosanon Heptakosanon Oktakosanon Nonakosanon Triakontanon Hentriakontanon Dotriakontanon Tritriakontanon Hektanon Dohektanon Trihektanon Kilianon Dilianatanon Trilianon C43H62 C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C500H10002 C600H1202 Tritetrakontanon Tetratetrakontanon Pentatetrakontanon Heksatetrakontanon Heptatetrakontanon Oktatetrakontanon Nonatetrakontanon Pentakontanon Henpentakontanon Dopentakontanon Tripentakontanon Tetrapentakontanon Pentapentakontanon heksapentakontanon Heptapentakontanon Oktapentakontanon Nonapentakontanon Heksa kontanon HenHeksa kontanon doHeksa kontanon triHeksa kontanon tetraHeksa kontanon pentaHeksa kontanon heksaHeksa kontanon Tetrahektanon Pentahektanon Heksahektanon Tetralianon Penliaanon Heksalianon C76H154 C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C700H14002 C800H16002 C900H18002 heksaHeptakontanon heptaHeptakontanon oktaHeptakontanon nonaHeptakontanon Oktakontanon henOktakontanon doOktakontanon triOktakontanon tetraOktakontanon pentaOktakontanon heksaOktakontanon heptaOktakontanon oktaOktakontanon nonaOktakontanon Nonakontanon henNonakontanon doNonakontanon triNonakontanon tetraNonakontanon pentaNonakontanon heksaNonakontanon HeptaNonakontanon oktaNonakontanon nonaNonakontanon Heptahektanon Oktahektanon Nonahektanon Heptalianon Oktalianon Nonalianon Sintesa alkanon a.

it is named 2-hydroxypropane1. the carbon in the carboxyl group does not count as being part of the main alkane chain. If there are multiple carboxyl groups on the same parent chain. -tricarboxylic acid.). The same is true for the prefix form. Reaksi-reaksi alkanon Alkanoat Main article: Carboxylic acids In general carboxylic acids are named with the suffix -oic acid (etymologically a back-formation from benzoic acid).3. R-ClC = O + R2Cd e. but do not have their position number indicated. For example. CrO3 + B2H6 H3O+ 3 R-C-R + CdCl2 (CH2)n C=O + BaCO3 + H2O CH3 CH3 O B 5. "carboxyl-". HOOC(CH2)nCOOH + BaO CH3 f.3-tricarboxylic acid.8. Citric acid is one example. although "systematic" names such as ethanoic acid are also acceptable. 2-hydroxypentanedioic acid. Senyawa CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 Nama Metanoat Etanoat Propanoat Butanoat Pentanoat Heksanoat Heptanoat Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 Nama tetratriakontanoat pentatriakontanoat heksatriakontanoat heptatriakontanoat oktatriakontanoat nonatriakontanoat Tetrakontanoat Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 Nama heptaHeksa kontanoat oktaHeksa kontanoat nonaHeksa kontanoat Heptakontanoat henHeptakontanoat DoHeptakontanoat triHeptakontanoat 82 .O d. As for aldehydes. CH3CH2CH2CH2COOH (valeric acid) is named pentanoic acid. rather than 2-carboxy. For common carboxylic acids some traditional names such as acetic acid are in such widespread use they are considered retained IUPAC names.2. etc. the suffix "-carboxylic acid" can be used (as -dicarboxylic acid. these are named as benzoic acid or its derivatives. In these cases. For carboxylic acids attached to a benzene ring such as PhCOOH. they take the "1" position on the parent chain.

RCH2CN + H2O f. RCH2COOX + H2O i. RCH2CH2OH + (O) b. RCH2COOR + H2O h. (RCH2CO2)2 + H2O RCH2COOH + NH3 RCH2COOH RCH2COOH + ROH RCH2COOH + HX 2 RCH2COOH 83 RCH2COOH R –CH2-COOH R –CH2-COOH RCH2COOH . RCH2CONH2 + H2O g. R-CH-CO-CH3 + NaOX d. R-CH2 MgX + CO2 + H+ H3O+ e.C8H18 C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 C3000H6002 Oktanoat Nonanoat Dekanoat Undekanoat Dodekanoat Tridekanoat Tetradekanoat Pentadekanoat Heksadekanoat Heptadekanoat Oktadekanoat Nonadekanoat Eikosanoat Heneikosanoat Dokosanoat Trikosanoat Tetrakosanoat Pentakosanoat Heksakosanoat Heptakosanoat Oktakosanaoat Nonakosanoat Triakontanoat Hentriakontanoat Dotriakontanoat Tritriakontanoat Hektanoat Dohektanoat Trihektanoat Kilianoat Dilianatanoat Trilianoat C41H58 C42H60 C43H62 C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C500H10002 C600H1202 Hentetrakontanoat5 Dotetrakontanoat Tritetrakontanoat tetratetrakontanoat Pentatetrakontanoat heksatetrakontanoat heptatetrakontanoat oktatetrakontanoat nonatetrakontanoat Pentakontanoat Henpentakontanoat dopentakontanoat tripentakontanoat tetrapentakontanoat pentapentakontanoat heksapentakontanoat heptapentakontanoat Oktapentakontanoat nonapentakontanoat Heksa kontanoat HenHeksa kontanoat doHeksa kontanoat triHeksa kontanoat tetraHeksa kontanoat pentaHeksa kontanoat heksaHeksa kontanoat Tetrahektanoat Pentahektanoat Heksahektanoat Tetralianoat Penliaanoat Heksalianoat C74H150 C75H152 C76H154 C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C700H14002 C800H16002 C900H18002 tetraHeptakontanoat pentaHeptakontanoat heksaHeptakontanoat heptaHeptakontanoat oktaHeptakontanoat nonaHeptakontanoat Oktakontanoat henOktakontanoat doOktakontanoat triOktakontanoat tetraOktakontanoat pentaOktakontanoat heksaOktakontanoat heptaOktakontanoat oktaOktakontanoat nonaOktakontanoat Nonakontanoat henNonakontanoat doNonakontanoat triNonakontanoat tetraNonakontanoat pentaNonakontanoat heksaNonakontanoat HeptaNonakontanoat oktaNonakontanoat nonaNonakontanoat Heptahektanoat Oktahektanoat Nonahektanoat Heptalianoat Oktalianoat Nonalianoat Sintesa alkanoat a. RCH2CH=O + Ag(NH3)2+ c.

g. and no location number is required since they always terminate a carbon chain. e. the longest carbon chain attached to the nitrogen atom becomes the primary name of the amine. the bonding position is infixed: CH3CH2CH2NH2 propan-1-amine. Senyawa amina adalah merupakan turunan hidrokarbon yang mempunyai gugus amina pada salah satu atau beberapa atom karbonnya dalam rantai molekul hidrokarbon. For secondary amines (of the form R-NH-R). CH3NH2 methanamine). Secondary and tertiary amides are treated similarly to the case of amines: alkane chains bonded to the nitrogen atom are treated as substituents with the location prefix N: HCON(CH3)2 is N.N-dimethylmethanamide. If necessary. The prefix form is "amino-". Amina digolongkan menjadi amina primer RNH2.Alkil amina Amines and Amides Main articles: Amine and Amide Amines (R-NH2) are named for the attached alkane chain with the suffix "-amine" (e. Again. dan amina tersier R3N yang ditentukan oleh derajad substuitusi atom nitrogennya Pemberina nama IUPAC dari senyawa amino didasrkan pada nama homolog induk alkil alkananya kemudian ditambah dengan amina dibelakangnya Amina alifatik 84 . amina sekunder R2NH. There is no prefix form. the substituent groups are ordered alphabetically. Tertiary amines (R-NR-R) are treated similarly: CH3CH2N(CH3)CH2CH2CH3 is N-ethyl-N-methylpropanamine. the other chain is prefixed as an alkyl group with location prefix given as an italic N: CH3NHCH2CH3 is N-methylethanamine. CH3CHNH2CH3 propan-2-amine. Amides (R-CO-NH2) take the suffix "-amide".g. CH3CONH2 (acetamide) is named ethanamide.

+ NaOH RRNH2X + NaOH RRRNHX + NaOH 85 R NH2 + NaX + H2O RRNH + NaX + H2O RRRN + NaX .Senyawa CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 C3000H6002 Nama Metil amiana Etetil amina Propil amina Butil amina Pentil amina Heksil amina Heptil amina Oktil amina Nonil amina Dekil amina Undekil amina Dodekil amina Tridekil amina Tetradekil amina Pentadekilamina Heksadekil amina Heptadekil amina Oktadekil amina Nonadekil amina Eikosil amina Heneikosil amina Dokosil amina Trikosil amina Tetrakosana Pentakosana Heksakosana Heptakosana Oktakosana Nonakosana Triakontana Hentriakontana Dotriakontana Tritriakontana Hektana Dohektana Trihektana kiliana Dilianatana Triliana Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 C41H58 C42H60 C43H62 C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C500H10002 C600H1202 Nama Tetratriakontil amina Pentatriakonil amina Heksatriakontil amina Heptatriakontil amina Oktatriakontil amina Nonatriakontil amina Tetrakontil amina Hentetrakontil amina Dotetrakontil amina Tritetrakontil amina Tetratetrakontil amina Pentatetrakontil amina Heksatetrakontil amina Heptatetrakontil amina Oktatetrakontil amina Nonatetrakontil amina Pentakontil amina Henpentakontana dopentakontana tripentakontana tetrapentakontana pentapentakontana heksapentakontana heptapentakontana Oktapentakontana nonapentakontana Heksa kontana HenHeksa kontana doHeksa kontana triHeksa kontana tetraHeksa kontana pentaHeksa kontana heksaHeksa kontana Tetrahektana Pentahektana Heksahektana Tetraliana Penliaana Heksaliana Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 C74H150 C75H152 C76H154 C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C700H14002 C800H16002 C900H18002 Nama heptaHeksakontil amina oktaHeksakontilamina nonaHeksakontil amina Heptakontil amina henHeptakontil amina DoHeptakontil amina triHeptakontana tetraHeptakontana pentaHeptakontana heksaHeptakontana heptaHeptakontana oktaHeptakontana nonaHeptakontana Oktakontana henOktakontana doOktakontana triOktakontana tetraOktakontana pentaOktakontana heksaOktakontana heptaOktakontana oktaOktakontana nonaOktakontana Nonakontana henNonakontana doNonakontana triNonakontana tetraNonakontana pentaNonakontana heksaNonakontana HeptaNonakontana oktaNonakontana nonaNonakontana Heptahektana Oktahektana Nonahektana Heptaliana Oktaliana Nonaliana Amina alisiklik Sikloamina Sintesa amina a. RX + RNH2 c. RX + NH3 b. RX + RRNH RNH3 X.

RX + NaCN h. RX + RRRN RRRNX + NaOH RN3 + LiAlH4 RCN + LiAlH4 C6H5NH2 RCH2NH2 RCH2NHR2 H2O ether H2O ether RRRRN + NaOH + H2O RNH2 RNH2 e. RX + NaN3 f. C6H5NO2 + Zn + HCl i.d. CH3COH + NH3 m. RCONH2 + Br2 + 4 KOH Alkil sulfide Senyawa CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 Nama Metil sulfida Etil sulfida Propil sulfida Butil sulfida Pentil sulfida Heksil sulfida Heptil sulfida Oktil sulfida Nonil sulfida Dekil sulfida Undekana Dodekana Tridekana Tetradekana Pentadekana Heksadekana Heptadekana Oktadekana Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 C41H58 C42H60 C43H62 C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 NOH NH2 C2H5OH Na sikloheksilhidroksiamin sikloheksilamin CH3CH2NH2 RNH2 + K2CO3 + 2 KBr + 2 H2O Nama Tetratriakontil sulfida Pentatriakontil sulfida Heksatriakontil sulfida heptatriakontana oktatriakontana nonatriakontana Tetrakontana hentetrakontana Dotetrakontana Tritetrakontana tetratetrakontana pentatetrakontana heksatetrakontana heptatetrakontana oktatetrakontana nonatetrakontana Pentakontana Henpentakontana Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 C74H150 C75H152 C76H154 C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 Nama heptaHeksa kontana oktaHeksa kontana nonaHeksa kontana Heptakontana henHeptakontana DoHeptakontana triHeptakontana tetraHeptakontana pentaHeptakontana heksaHeptakontana heptaHeptakontana oktaHeptakontana nonaHeptakontana Oktakontana henOktakontana doOktakontana triOktakontana tetraOktakontana 86 . RCONR2 + LiAlH4 O k. + H2NOH Sikloheksanon H2/Ni l. RCN + LiAlH4 j.

C = C + H2O c.C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 C3000H6002 Nonadekana Eikosana Heneikosana Dokosana Trikosana Tetrakosana Pentakosana Heksakosana Heptakosana Oktakosana Nonakosana Triakontana Hentriakontana Dotriakontana Tritriakontana Hektana Dohektana Trihektana kiliana Dilianatana Triliana C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C500H10002 C600H1202 dopentakontana tripentakontana tetrapentakontana pentapentakontana heksapentakontana heptapentakontana Oktapentakontana nonapentakontana Heksa kontana HenHeksa kontana doHeksa kontana triHeksa kontana tetraHeksa kontana pentaHeksa kontana heksaHeksa kontana Tetrahektana Pentahektana Heksahektana Tetraliana Penliaana Heksaliana C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C700H14002 C800H16002 C900H18002 pentaOktakontana heksaOktakontana heptaOktakontana oktaOktakontana nonaOktakontana Nonakontana henNonakontana doNonakontana triNonakontana tetraNonakontana pentaNonakontana heksaNonakontana HeptaNonakontana oktaNonakontana nonaNonakontana Heptahektana Oktahektana Nonahektana Heptaliana Oktaliana Nonaliana H2O a. RX + H2S b. R-CH = CH2 + B2H6 RSH + HX -CH – CHOH (RCH2– CH2)3-B+ H2O2 OH H2O - RCH2– CH2OH R-CH = CH3 OH d. R-CH = CH2 + Hg(OCOCH3)2 25 oC R-CH = CH2 + NaBH4 OH HgOCOCH3 Alkil fosfat adalah senyawa organic yang mengandung gugus posfat dengan rumus umum sebagai berikut : R-PO3H2 Senyawa CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 Nama Metil posfat Etil posfat Propil posfat Butane Pentane Heksana Heptana Oktana Nonana Dekana Senyawa C34H44 C35H46 C36H48 C37H50 C38H52 C39H54 C40H56 C41H58 C42H60 C43H62 Nama tetratriakontana pentatriakontana heksatriakontana heptatriakontana oktatriakontana nonatriakontana Tetrakontana hentetrakontana Dotetrakontana Tritetrakontana Senyawa C67H136 C68H138 C69H140 C70H142 C71H144 C72H146 C73H148 C74H150 C75H152 C76H154 Nama heptaHeksa kontana oktaHeksa kontana nonaHeksa kontana Heptakontana henHeptakontana DoHeptakontana triHeptakontana tetraHeptakontana pentaHeptakontana heksaHeptakontana 87 .

2005) s . p blocks 88 . Organometallics is the branch of chemical science studying the chemistry of molecules that have direct carbon-metal bonds.C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42 C21H44 C22H46 C23H48 C24H50 C25H52 C26H54 C27H56 C28H58 C29H60 C30H62 C31H64 C32H66 C33H68 C100H202 C200H402 C300H6002 C1000H2002 C2000H4002 C3000H6002 Undekana Dodekana Tridekana Tetradekana Pentadekana Heksadekana Heptadekana Oktadekana Nonadekana Eikosana Heneikosana Dokosana Trikosana Tetrakosana Pentakosana Heksakosana Heptakosana Oktakosana Nonakosana Triakontana Hentriakontana Dotriakontana Tritriakontana Hektana Dohektana Trihektana kiliana Dilianatana Triliana C44H64 C45H66 C46H68 C47H70 C48H72 C49H74 C50H102 C51H104 C52H106 C53H108 C54H110 C55H112 C56H114 C57H116 C58H118 C59H120 C60H122 C61H124 C62H126 C63H128 C64H130 C65H132 C66H134 C400H802 C500H1002 C600H12002 C400H8002 C500H10002 C600H1202 tetratetrakontana pentatetrakontana heksatetrakontana heptatetrakontana oktatetrakontana nonatetrakontana Pentakontana Henpentakontana dopentakontana tripentakontana tetrapentakontana pentapentakontana heksapentakontana heptapentakontana Oktapentakontana nonapentakontana Heksa kontana HenHeksa kontana doHeksa kontana triHeksa kontana tetraHeksa kontana pentaHeksa kontana heksaHeksa kontana Tetrahektana Pentahektana Heksahektana Tetraliana Penliaana Heksaliana C77H156 C78H158 C79H160 C80H162 C81H164 C82H166 C83H168 C84H170 C85H172 C86H174 C87H176 C88H178 C89H180 C90H182 C91H184 C92H186 C93H188 C94H190 C95H192 C96H194 C97H196 C98H198 C99H200 C700H1402 C800H1602 C900H1802 C700H14002 C800H16002 C900H18002 heptaHeptakontana oktaHeptakontana nonaHeptakontana Oktakontana henOktakontana doOktakontana triOktakontana tetraOktakontana pentaOktakontana heksaOktakontana heptaOktakontana oktaOktakontana nonaOktakontana Nonakontana henNonakontana doNonakontana triNonakontana tetraNonakontana pentaNonakontana heksaNonakontana HeptaNonakontana oktaNonakontana nonaNonakontana Heptahektana Oktahektana Nonahektana Heptaliana Oktaliana Nonaliana Biasanya senyawa alkyl posfat terdapat dalam molekul DNA dan RNA.d. (Dec 30.

M-alkyl β-elimination π-acceptor bonding alkene complexes CO complexes 89 . Crystal field theory Single σ-bonding 1. Na. K organyls Be organyls Mg organyls Aluminium group Silicon group • • Si organyls Ga organyls Pb. Hg Transition-metal organometallic chemistry The organometallic chemistry of the transition elements is quite different from the main-group ones due to the availability for bonding of the n d orbitals with consequent ability for the central atom to change geometry and expand the octet.Main group organometallic chemistry Alkali and akaline earths organometallic • • • Li. Sb. Sn.

The partial filling of the π* orbital leads to a weakened C-O triple bond. σ *→dσ 2. Free CO V(CO)6 Ni(CO)4 Cr(CO)6 2143 1976 2057 2000 Arene complexes Carbenes and carbynes compounds Fischer carbenes By treatment of a CO complex with a strong nucleophile Schrock carbenes Catalysis by organometallic compounds Metathesis Richard Schrock(MIT. USA) and Robert Grubbs (CalTech. In fact. Metathesis is the exchange of the termination between two alkenes [1] It occurs via the carbene species nowaday known as Schrock's carbenes 90 . as showed from the stretching frequencies (in cm-1) of CO free and in M/CO complexes. the second interaction. USA) received 2005 Nobel prize for their work on the subject. as known as pi backbonding increases the available electron density on the CO.1. dπ→π * These interactions are synergicin increading the M-CO bond strength.

Olefin metathesis.1. ^ Grubbs. Tetrahedron Ziegler-Natta polymerisation Ziegler-Natta catalyst Ziegler in the 40's worked on the oligomerisation of ethylene by aluminium alkyls via the reaction HAl-R + CH2=CH2 -> HAl-CH2CH2-R Enantioselective hydrogenation Wilkinson's 91 .

HCO(CO)5 Fischer-Tropsch synthesis Fischer-Tropsch synthesis is the heterogeneously-catalysed formation of hydrocarbons (alkanes and alkenes) from CO and hydrogen (synthesis gas). TEORI TENTANG STEREO KIMIA Reaksi inversi Walden Pada tahun 1896 seorang ahli kimia Jerman yang bernama Paul Walden menemukan peralihan bentuk isomer dari bentuk enasiomer asam malat (+) menjadi bentuk asam malat (-). Organometallics in living systems The only example of a biological molecule containing direct carbon-metal bonds is cobalamin. 92 . Bila bentuk isomer asam malat (-) direaksikan dengan PCl 5 maka akan terbentuk isomer asam klorosuksinat (+). It is the heart of the gas-to-liquids processes developed commercially by big petrochemical firms in the 90's.Hydroformylation Hydroformylation Hydroformylation is the process that transforms an alkene into an aldehyde by reaction with CO. Bila asam khloro suksinat (+) direaksikan dengan Ag2O. perubahan bentuk enansiomer ini terjadi melalui sederet siklus reaksi substitusi sederhana. VI. It can be seen as the inverse of synthesis gas preparation (although this is usually from methane and lighter hydrocarbons). as known as vitamin B12 MODUL VI. The catalyst is a hydridocarbonyl complex.

3 Stereokimia dan reaksi substitusi nukleofilik Sekalipun pada reaksi inverse Walden di atas terjadi perubahan konfigurasi yang berlangsung dalam suatu siklus reaksi.2. Bila asam malat (+) direaksikan dengan PCl 5 dalam eter akan terbentuk isomer asam klorosuksinat (-). menemukan bahwa adanya gugus asam karboksilat pada perlakuan Walden membuat masalah jadi rumit. namun tahap-tahap detil dari reaksi tersebut belum bisa diketahui.maka akan terbentuk asam malat (+). oleh karena itu dia melakukan reaksi yang lebih sederhana. Akan tetapi pada tahun 1920an Joseph Kenyon dan Henry Philips melalui sederet pengujian yang dirancang untuk menentukan stereokimia dari reaksi substitusi. Diantara sekian banyak pengujiannya dia meneliti peralihan dua isomer 1fenil2propanol dengan reaksi sebagai berikut : 93 . OH HO2C-CH2-CH-CO2H PCl5 Asam malat (-) [ a]D = .3 Ag2O H2O Cl HO2C-CH2-CH-CO2H PCl5 asam klorosuksinat (-) Cl HO2C-CH2-CH-CO2H asam klorosuksinat (+) Ag2O H2O OH HO2C-CH2-CH-CO2H Asam malat (+) [ α]D = 2. Selanjutnya bila asam kloro suksinat (-) direaksikan dengan Ag2O dalam air akan terbentuk asam malat (-).

2o .0o 94 [a]D = 33.OH -CH-CH-CH3 fenil-2propanol [a]D = 33o O-Tos -CH-CH-CH3 [a]D = 31.C-CH3 -CH-CH-CH3 O-C-CH3 CH3 O -CH-CH-O-C-CH3 [a]D = 7o [a]D = -7o CH3 -CH2CH-O-Tos -CH2-CH-OH CH3 [a]D = 31.1o O HOH2O O O.

dan reaksi kadang-kadang bersaing satu sama lain Sangat penting untuk memahami bahwa substitusi dan eliminasi reaksi tidak berhubungan dengan senyawa tertentu atau campuran begitu banyak karena mereka representasi dari bagaimana reaksi tertentu terjadi. dibahas kemudian di bagian ini. Penentuan kecepatan rreaksi dan ketergantungan kecepatan reaksi terhadap konsentrasi reagen merupakan cara yang bisa digunakan untuk menentukan mekanisme reaksi. dan umumnya ide yang baik untuk mempelajari reaksi bersama-sama. Kadang-kadang. Kinetika reaksi substitusi elekrofilik MEKANISME REAKSI SUBSTITUSI (SN) DAN ELIMINASI (E) Reaksi Substitusi Nukleofilik Reaksi substitusi nukleofilik (SN1 dan SN2) sangat erat kaitannya dengan E1 dan reaksi eliminasi E2.+ CH3Br ------------. karena ada kesejajaran dalam mekanisme reaksi. substrat yang disukai. Kecepatan pada saat bahan baku bereaksi memebntuk produk disebut kecepatan reaksi.HO-CH3 + BrKecepatan reaksi = kecepatan hilangnya konsentrasi bahan baku = k x [RX] x [HO-] Dimana k = konstanta kecepatan reaksi [RX] = konsentrasi CH3Br [HO-] = konsentrasi HOReaksi SN1 Reaksi SN1 berati reaksi ini adalah reaksi substusi nukleofilik Orde satu. Reaksi SN2 Reaksi SN2 erati reaksi ini adalah reaksi substusi nukleofilik Orde dua. Dari reaksi substitusi nukleofilik berikut : H. kombinasi dari mekanisme ini dapat terjadi bersama dalam reaksi yang sama atau mungkin bersaing satu sama lain. yang besarnanya dapat diukur. dengan pengaruh seperti pilihan pelarut atau nukleofil menjadi faktor penentu untuk yang reaksi akan mendominasi.Kinetika Reaksi substitusi nukleofilik Para ahli kimia telah sepakat bahwa secara kualitatif suatu reaksi ditentukan oleh reaksi yang lambat. 95 .

Kedua mekanisme yang berbeda menjelaskan perbedaan dalam laju reaksi antara SN1 dan SN2 reaksi. 96 . Dengan demikian laju reaksi adalah reaksi orde kedua: Tingkat = k [Nu:] [RX] (di mana Nu: adalah nukleofil menyerang) Reaksi SN2 Ada terutama 3 hal yang mempengaruhi apakah reaksi SN2 akan berlangsung atau tidak. atau tersier. Reactivity Due to Structure of SN2 CH3X > RCH2X > R2CHX >> R3CX Struktur alkil halida memiliki efek yang besar pada mekanisme. Reaksi SN2. langkah tunggal nukleofil yang datang bersama-sama dengan reaktan dari sisi berlawanan dari kelompok pergi. laju reaksi adalah reaksi orde pertama yang tingkat tergantung hanya pada langkah itu. CH3X & RCH2X adalah struktur yang lebih disukai untuk SN2. dalam reaksi SN2. sebuah elektrofil dengan sekelompok meninggalkan Sekelompok meninggalkan adalah bagian bermuatan atau netral (kelompok) yang memecah gratis. primer. Kedua hal ini terjadi dalam satu langkah. karena afinitas tinggi untuk dan ikatan kuat dengan karbon. diprakarsai oleh disosiasi dari kelompok pergi. memaksa kelompok meninggalkan pergi. Ini adalah tingkat membatasi langkah dan dengan demikian. karbon sekunder. terlibat dalam reaksi SN2. adalah nucleophilicity dari nukleofil dan pelarut yang digunakan dalam reaksi. Substitusi nukleofilik memerlukan 1. di sisi lain. jika pernah. angka ini tergantung pada kedua konsentrasi nukleofil serta konsentrasi reaktan. adalah kunci untuk menilai nya. dan R3CX jarang. nukleofil menyerang molekul dan mengambil tempat lain nukleofil. adalah reaksi 1-langkah di mana nukleofil menyerang. Karena itu. semakin sering tabrakan. nukleofil (seperti basa Lewis) 2. SN1 vs SN2 Salah satu perbedaan utama antara SN1 dan SN2 adalah bahwa reaksi SN1 adalah reaksi 2-langkah. Para nukleofil yang meninggalkan disebut kelompok pergi. R2CHX dapat menjalani SN2 di bawah kondisi yang tepat (lihat bawah). Dua lainnya komponen yang menentukan apakah reaksi SN2 akan berlangsung atau tidak. yang kemudian meninggalkan. Yang ini lebih tinggi dua konsentrasi. Itu adalah apakah alkil halida adalah pada metil. Rate = k[RX] Atau. SN1 reaksi tergantung pada kelompok meninggalkan tidak dikaitkan dengan karbon. Yang paling penting adalah struktur. S adalah singkatan dari substitusi (sesuatu mengambil tempat sesuatu yang lain) N: singkatan nukleofilik (a menggantikan nukleofil nukleofil lain) 1: singkatan unimolecular (konsentrasi hanya satu jenis molekul menentukan laju reaksi) 2: singkatan Bimolekular (konsentrasi dua jenis molekul menentukan laju reaksi) Dalam substitusi nukleofilik.mencatat Dalam notasi SN1 dan SN2.

lebih terpolarisasi. nukleofil. Ion bromida adalah kelompok pergi. Tidak ada nomor tertentu atau satuan ukuran yang digunakan. karbon tersier (R3CX) begitu sterik terhalang untuk mencegah mechanim SN2 dari mengambil tempat sama sekali. contoh: OH-+ CH3-Cl → HO-CH3 + ClOH-adalah nukleofil tersebut. nucleophilicity adalah kuat. menyerang molekul metil bromida. meninggalkan ion iodida bebas untuk menyerang CH-Br molekul. karena meningkatnya jumlah R kelompok. Semua hal lain dianggap sama. Perhatikan bahwa 3 lainnya Obligasi ini semua menunjuk jauh dari brom dan terhadap nukleofil menyerang. Umumnya.Reaksi berlangsung oleh nukleofil menyerang dari sisi berlawanan dari atom brom. ini berbeda dengan hasil reaksi SN1. Semua nukleofil adalah basa Lewis. SN2 reaksi lebih disukai untuk metil halida dan halida primer. 97 . Na + I-+ CH3-Br → CH3 I-Na + + BrReaksi di atas. sehingga lebih sulit bagi nukleofil untuk mendapatkan cukup dekat dengan karbon α-. untuk mengusir atom brom. yang nukleofil disukai adalah nukleofil kuat yang merupakan basa lemah. Hal penting lain yang perlu diingat. seperti daun brom dan obligasi nukleofil pada karbon-α. obligasi lainnya melipat kembali menjauh dari nukleofil tersebut. dan ini dapat dilihat dengan jelas dalam contoh di atas. pelarut dan iodida memisahkan hampir sepenuhnya dalam aseton. Hubungan ini generalisasi sebagai hal-hal seperti pelarut dan substrat dapat mempengaruhi harga relatif. I-. Sebagai contoh. Contoh dari ini adalah N3-. ada hinderance sterik sangat sedikit dari nukleofil yang mendekat. Cl adalah elektrofil. obligasi ini menjadi planar dengan karbon dan. nukleofil umumnya dibandingkan satu sama lain dalam hal reaktivitas relatif. Ion iodida bermuatan negatif. di mana konfigurasi R akan dikonversi menjadi konfigurasi S dan sebaliknya. Nucleophilicity Nucleophilicity adalah tingkat di mana nukleofil memindahkan kelompok berangkat reaksi. Saat ini 3 obligasi adalah obligasi hidrogen. Bahkan. Seperti yang akan Anda lihat di bawah. Hal ini sangat penting dalam molekul kiral atau pro-kiral. molekul mengalami inversi sebuah. memaksa dari ion bromida bermuatan negatif dan mengambil tempat. selama reaksi SN2. yang berlangsung di aseton sebagai natrium. nukleofil yang lebih besar. dan Cl-adalah kelompok pergi. RS-. Dalam kasus contoh ini. sekunder α-karbon. dan / atau kurang stabil. dan CN-. masih banyak hinderance sterik dan dan apakah mekanisme SN2 akan terjadi akan tergantung sepenuhnya pada apa yang nukleofil dan pelarut. Br-. tapi mereka umumnya pedoman baik untuk spesies yang membuat nukleofil terbaik. demikian juga hinderance sterik. Namun. HOCH3 adalah produk. sebuah nukleofil kuat tertentu mungkin memiliki reaktivitas relatif dari 10. Selama keadaan transisi.000 yang dari nukleofil lemah tertentu. Obligasi melekat pada karbon-α yang menjauh sebagai pendekatan nukleofil. atau. Dalam reaksi SN2.

The SN2 mechanism is preferred when the solvent is an aprotic. a solvent that is polar. 98 . forms a 'cage' of hydrogen-bonded solvent around the nucleophile. List of descending nucleophilicities I.>> F. Solvent can also have a great effect on reaction rate of SN2 reactions. A polar solvent is preferred because it better allows the dissociation of the halide from the alkyl group. protic solvents would include water. pelarut Pelarut dapat memainkan peran penting dalam reaksi SN2.> Br.> Br. but without a polar hydrogen. termasuk RO-dan OH-. ini adalah ion halida yang meninggalkan atom karbon ketika serangan nukleofil. polar solvents are HMPA. Good aprotic. and DMF. Dalam hal suatu alkil halida. khususnya di SN2 melibatkan substrat sekunder alkil halida. and generally. however.> Cl.Atau. A protic solvent with a polar hydrogen. dimana dapat menjadi faktor penentu dalam mekanisme. Kecenderungan nukleofil untuk meninggalkan adalah Relative Reactivity of Leaving Groups I. Polar. where it can be the determining factor in mechanism. seperti yang disebutkan sebelumnya dalam teks. DMSO. Namun.> Cl.> -SeH > -OH > H2O meninggalkan Grup Membiarkan kelompok adalah kelompok pada substrat yang meninggalkan. kadang-kadang mekanisme reaksi bersaing dan dalam kasus sebuah nukleofil kuat itu dasar yang kuat. Pelarut juga dapat memiliki efek besar pada laju reaksi SN2 reaksi.>> FFluoride ions are very poor leaving groups because they bond very strongly and are very rarely used in alkyl halide substitution reactions. CH3CN. polar solvent. mekanisme SN2 akan bersaing dengan mekanisme E2. particularly in SN2 involving secondary alkyl halide substrates. Reactivity of a leaving group is related to its basicity with stronger bases being poorer leaving groups. Contoh nukleofil kuat yang juga basa kuat. That is. sebuah nukleofil kuat yang juga merupakan dasar yang kuat juga dapat bekerja. Solvent The solvent can play an important role in SN2 reactions. hindering its approach to the substrate. alcohols. solvents with polar NH or OH bonds.

Baik aprotik. bagaimanapun. tetapi tanpa hidrogen kutub. 99 . depending on the solvent. aprotik pelarut polar. alkohol. dan DMF. its exactly the opposite and. is quite different and because of this. let's take a look at how the SN1 mechanism works. The role of structure in the SN1 mechanism. pelarut protik akan mencakup air. membentuk sebuah 'kandang' hidrogen ikatan pelarut sekitar nukleofil itu. dan umumnya. in some cases. menghambat pendekatannya terhadap substrat. pelarut polar adalah HMPA. DMSO.Mekanisme SN2 lebih disukai bila pelarut adalah. The SN1 mechanism does not operate on primary alkyl halides or methyl halides. CH3CN. suatu pelarut yang polar. Reactivity Due to Structure of SN1 CH3X < RCH2X << R2CHX < R3CX The SN1 mechanism is preferred for tertiary alkyl halides and. Sebuah pelarut polar lebih disukai karena lebih baik memungkinkan pemisahan halida dari kelompok alkil. To understand why this is so. Artinya. however. the reactivity of structures is more or less reversed. Like the SN2 mechanism. structure plays an important role in the SN1 mechanism. Relative Reactivity of Solvents HMPA > CH3CN > DMF > DMSO >> H2O SN1 Reactions The SN1 mechanism is very different from the SN2 mechanism. Polar. the results of the reaction can be significantly different. may be preferred in secondary alkyl halides. Sebuah pelarut protik dengan hidrogen kutub. In some of its preferences. pelarut polar dengan NH atau obligasi OH.

Primary and methyl carbocations however. the first step is the spontaneous dissociation of the halide from the alkyl halide. In the SN1 mechanism. there is an inversion caused by the nucleophile attacking from the opposite side while the halide is still bonded to the carbon. In theSN2 reactions. where the attacking nucleophile causes the halide to leave. Since we know tertiary carbocations are the most stable. In the SN1 mechanism. the water acts as a nucleophile to bond to the carbocation. And with appropriate conditions. As with structure. a racemic mixture. In the final step. the reasons differ. At the top of the diagram. the SN1 mechanism depends on the ability of the halide to leave on its own. secondary carbocations will also operate by the SN1 mechanism. Once the halide has dissociated. The polarity of the solvent is associated with the dielectric constant of the solvent and solutions with high dielectric constants are 100 . leaving an alcohol.SN1 nucleophilic substitution of a generic halide with a water molecule to produce an alcohol. In particular. the stability of the carbocation is crucial to the ability of the halide to leave. This results in. This requires certain conditions. and the bonds off of the α-carbon have become planar. Solvent Like the SN2 mechanism. protic solvent is used. however. Unlike the SN2 mechanism. a polar. the SN1 is affected by solvent as well. since the halide has left. Note: Racemic mixtures imply entirely equal amounts of mixture. primarily. they are the best candidates for the SN1 mechanism. are not stable enough to allow this mechanism to happen. one of the hydrogens of the bonded water molecule is attacked by another water molecule. This is the result some steric hinderence from the leaving halide which is sometimes close enough to the leaving side to block the nucleophile's approach from that side. There is a slight tendency towards attack from the opposite side of the halide. the water molecule is free to attack from either side. however this is rarely the case in SN1.

better able to support separated ions in solution. In SN2 reactions, we were concerned about polar hydrogen atoms "caging" our nucleophile. This still happens with a polar protic solvent in SN1 reactions, so why don't we worry about it? You have to keep in mind the mechanism of the reaction. The first step, and more importantly, the rate-limiting step, of the SN1 reaction, is the ability to create a stable carbocation by getting the halide anion to leave. With a polar protic solvent, just as with a polar aprotic solvent,we're creating a stable cation, however it's the polar hydrogens that stabilize the halide anion and make it better able to leave. Improving the rate-limiting step is always the goal. The "caging" of the nucleophile is unrelated to the rate-limiting step and even in its "caged" state, the second step, the attack of the nucleophile, is so much faster than the first step, that the "caging" can simply be ignored.

Summary
SN1, SN2, E1, and E2, are all reaction mechanisms, not reactions themselves. They are mechanisms used by a number of different reactions. Usually in organic chemistry, the goal is to synthesize a product. In cases where you have possibly competing mechanisms, and this is particular the case where an SN1 and an E1 reaction are competing, the dominating mechanism is going to decide what your product is, so knowing the mechanisms and which conditions favor one over the other, will determine your product. In other cases, knowing the mechanism allows you to set up an environment favorable to that mechanism. This can mean the difference between having your product in a few minutes, or sometime around the next ice age. So when you're designing a synthesis for a product, you need to consider, I want to get product Y, so what are my options to get to Y? Once you know your options and you've decided on a reaction, then you need to consider the mechanism of the reaction and ask yourself, how do I create conditions that are going to make this happen correctly and happen quickly? Reaksi eliminasi Reaksi substitusi nukleofilik dan reaksi Penghapusan berbagi banyak karakteristik umum, di atas yang, E1 dan SN1 serta E2 dan SN2 reaksi kadang-kadang dapat bersaing dan, karena produk mereka berbeda, penting untuk memahami keduanya. Tanpa memahami kedua jenis mekanisme, akan sulit untuk mendapatkan produk yang anda inginkan dari reaksi. Selain itu, SN1 dan SN2 reaksi akan dirujuk cukup sedikit dengan cara perbandingan dan kontras, jadi mungkin lebih baik untuk membaca bagian yang pertama dan kemudian lanjutkan di sini. Reaksi eliminasi adalah mekanisme untuk menciptakan produk alkena dari reaktan haloalkana. E1 dan E2 eliminasi, tidak seperti SN1 dan SN2 substitusi, mekanisme tidak terjadi dengan metil halida karena reaksi menciptakan ikatan ganda antara dua atom karbon dan methylhalides hanya memiliki satu karbon.

mencatat Dalam notasi E1 dan E2, E adalah singkatan dari eliminasi 1: singkatan unimolecular (konsentrasi hanya satu jenis molekul menentukan laju reaksi) 2: singkatan Bimolekular (konsentrasi dua jenis molekul menentukan laju reaksi) 101

E1 vs E2 reaksi harga E1 dan E2 adalah dua jalur yang berbeda untuk menciptakan alkena dari haloalkanes. Seperti SN1 dan SN2 reaksi, salah satu perbedaan utama adalah dalam laju reaksi, karena menyediakan wawasan besar ke dalam mekanisme. Reaksi E1, seperti SN1 reaksi adalah 2-langkah reaksi. Juga seperti reaksi SN1, tingkat membatasi langkah adalah disosiasi dari halida dari alkana nya, sehingga reaksi orde pertama, tergantung pada konsentrasi haloalkana, dengan laju reaksi dari: Tingkat = k [RX] Di sisi lain, reaksi E2, seperti reaksi SN2 1-langkah reaksi. Dan lagi, seperti dengan reaksi SN2, tingkat membatasi langkah adalah kemampuan nukleofil untuk melampirkan alkana dan menggantikan halida. Jadi itu adalah reaksi orde kedua yang tergantung pada konsentrasi dari kedua nukleofil dan haloalkana, dengan tingkat reaksi: Tingkat = k [Nu:] [RX] (di mana Nu: adalah nukleofil menyerang) Zaitsev di Peraturan Aturan Zaitsev itu (kadang-kadang dieja "Saytzeff") menyatakan bahwa dalam reaksi eliminasi, ketika beberapa produk yang mungkin, alkena paling stabil adalah produk utama. Artinya, yang paling sangat alkena tersubstitusi (dalam alkena dengan hidrogen sebagian besar non-substituen), adalah produk utama. Kedua E1 dan E2 reaksi menghasilkan campuran produk, bila mungkin, tetapi umumnya mengikuti aturan Zaitsev itu. Kita akan lihat di bawah mengapa reaksi E1 mengikuti aturan Zaitsev yang lebih andal dan cenderung menghasilkan produk yang lebih murni.

102

Dehidrohalogenasi reaksi (S)-2-bromo-3-metilbutana Gambar di atas merupakan dua jalur yang mungkin untuk dehidrohalogenasi dari (S)-2-bromo-3metilbutana. Kedua produk potensial adalah 2-methylbut-2-ena dan 3-methylbut-1-ene. Gambar di kanan disederhanakan gambar dari produk molekul ditunjukkan pada gambar di tengah. Seperti yang Anda lihat di sebelah kiri, bromin adalah pada karbon kedua dan dalam reaksi E1 atau E2, hidrogen bisa dihapus baik dari 1 atau karbon 3. Aturan Zaitsev mengatakan bahwa hidrogen akan dihapus terutama dari karbon ke-3. Pada kenyataannya, akan ada campuran, tetapi sebagian besar produk akan 2-methylbut-2-ena oleh mekanisme E1. Dengan reaksi E2, seperti yang akan kita lihat nanti, ini mungkin tidak selalu menjadi kasus.

E2 Reactivity Due to Structure of E2
RCH2X > R2CHX >> R3CX Mekanisme E2 adalah terpadu dan higly stereospesifik, karena dapat terjadi hanya jika H dan X kelompok meninggalkan berada dalam posisi anti-coplanar. Artinya, dalam proyeksi Newman, H dan X harus 180 °, atau anti-konfigurasi. Perilaku ini berakar dari tumpang tindih terbaik dari orbital 2p dari karbon yang berdekatan ketika ikatan pi harus terbentuk. Jika H dan meninggalkan kelompok tidak dapat dibawa ke dalam posisi ini karena struktur molekul, mekanisme E2 tidak akan terjadi.

Mechanism of E2 elimination. Note the anti-coplanarity of the X-C-C-H atoms Karena itu, hanya memiliki molekul diakses HX anti-coplanar konformasi dapat bereaksi melalui rute ini. Selanjutnya, mekanisme E2 akan beroperasi bertentangan dengan aturan Zaitsev kalau hidrogen anti-coplanar hanya dari hasil kelompok meninggalkan dalam alkena paling stabil. Sebuah contoh yang baik tentang bagaimana ini bisa terjadi adalah dengan melihat bagaimana sikloheksana dan turunannya sikloheksena mungkin beroperasi dalam kondisi E2

103

to understand the geometry of the molecule. Coplanar implies precisely 180 degree separation and "peri-". angled a little down from the plane and towards the viewer.(ethanolate). 104 .E2 with preferential elimination Let's look at the example above. the chlorine atom is actually slightly less than 180 degrees from both the hydrogen and the isopropyl group. from Greek for "near". periplanar might be a more correct term. As you can see from the Newman projection. The images below shows the molecule after a ring flip. In this conformation. so it's the only one eligible for the E2 mechanism. There are 3 hydrogens off of the carbons adjacent to our chlorinated carbon. so in this case. So it's important. the product is going to be only 3-isopropylcylcohex-1-ene. no product is possible. implies near 180 degrees. Because of this. the mechanism that dominates is E2. because of molecular forces. Note: Often the word periplanar is used instead of coplanar. In the case of the 1-chloro-3-isopropylcyclohexane example. The red hydrogen is the only hydrogen that's 180° from the chlorine atom. the products. By his rule. The third would be hard to show but is attached to the same carbon as the red hydrogen. Periplanar may actually be more accurate. The red and the green ones are two of them. there are no hydrogens 180° from the chlorine atom. The reactant we're using is 1-chloro-2-isopropylcyclohexane. Notice how this is contrary to Zaitsev's rule which says the most substituted alkene is preferred. when considering the E2 mechanism. However it simply can't be produced because of the steric hindrance. for example CH3CH2O. Sometimes the geometry can be used to your advantage to preferentially get a single product. Other times it will prevent you from getting the product you want. as that would leave the most substituted alkene. 1-isopropylcyclohexene should be our primary product. The drawing at the top left is one conformation and the drawing below is after a ring flip. and you'll need to consider a different mechanism to get your product. If we assume we're treating the 1-chloro-2-isopropylcyclohexane with a strong base. In the center are Newman projections of both conformations and the drawings on the right.

Consider the first atom of each part of the molecule. This is the same way the SN1 reaction begins. producing a carbocation on the alkyl group and a leaving anion. In SN1 reactions. More specifically. I > Cl > C > H) 105 . In E1 reactions. The rules have evolved to cover many situations. the action of the nucleophile. What makes the difference between whether the reaction takes the SN1 or E1 pathway then. PUSAT CHIRAL Campuran rasemat Senyawa stereo isomer Proyeksi struktur molekul organic Stereoisomers are properly named using the Cahn-Ingold-Prelog (CIP) priority rules to decide which parts of the molecule to consider first.g. help initiate the step in E1 reactions. Senyawa optis aktif Beberapa model enansiomer MODUL VII VIII. An atom with higher atomic number has higher priority. The nucleophile/base then extracts the hydrogen causing the bonding electrons to fall in and produce a pi bond with the carbocation. (e. a polar protic solvent is preferred because the polar aspect stabilizes the carbocation and the protic aspect stabilizes the anion. must depend on the second step. The choice of solvent is the same as SN1 as well. a strong nucleophile that's a weak base is preferred. causes the nucleophile to attack the hydrogen at the β-carbon instead of the αcarbocation.E1 E1 elimination of an alkyl halide by a base The E1 mechanism begins with the dissociation of the leaving group from an alkyl. The nucleophile will then attack and bond to the carbocation. a strong nucleophile is still preferred. secondary and tertiary carbocations are preferred because they're more stable than primary carbocations. so the same thing that helps initiate that step in SN1 reactions. The difference is that a strong nucleophile that's also a strong base. but the basic rules are: 1. VII.

2. Sebuah searah jarum jam adalah R (latin: rektus) konfigurasi. -C(CH3)3 > -CH(CH3)2 > -CH2CH3 > -CH3). menunjukkan atom prioritas terendah menjauh dari Anda. Realize that when you do this it will mean that sometimes groups with higher total weights will have lower priority because of a lower weight of the atom that connects them. jumlah atom karbon sama dengan jumlah molekul air dimana nilai n adalah bilangan bulat lebih Klassifikasi karbohidrat 106 .org/wiki/Organic_Chemistry/Chirality/R-S_notational_system" Subject: Organic Chemistry MODUL VIII IX.wikibooks. KARBOHIDRAT (saccharida ) Karbohidrat adalah suatu molekul senyawa organic dengan rumus umum Cn(H2O)n.saat ini sedang disukai. Dasarnya. Sebuah arah berlawanan adalah S (latin: jahat) konfigurasi. consider the next atoms until there is a difference. consider the second atom(s) in the same way as the first.g. adalah lagi aturan prioritas CIP. Prioritas ini didasarkan pada nomor atom. Kedua. If the first atom of two groups is the same. (e. See main discussion: E-Z notation Retrieved from "http://en. [edit] R & S Notation R-dan S-notasi menggunakan aturan prioritas CIP untuk tugas dari konfigurasi mutlak sekitar stereocenter. If this does not assign priority.hanya berlaku untuk konfigurasi absolut dari pusat memiliki ikatan tunggal saja. cis / trans nomenklatur sistem tradisional tidak cukup akurat dan E-/Z. Ikuti arah 3 prioritas yang tersisa dari terendah hingga tertinggi. menetapkan prioritas untuk setiap atom yang mengelilingi stereocenter. Direction of the travel 1-2-3 dictates configuration [edit] E-Z notation Notasi R-/S. Dalam hal ikatan ganda. Pertama.

aldotriosa O H OH CH2OH D-Gliseraldehid 9.1. Aldosa 9.1. Monosaccharida Struktur yang paling sederhana dari aldosa adalah gliseral dehid dengan 1 atom C optis aktif (puat Chiral).1.1. konfigurasi karbohidrat 9. Konfigurasi karbohidrat ada 2 macam : 9. Gliseral dehid mempunyai dua bentuk enasiomer yakni D-Gliseral dehid dan L-gliseraldehid.1. Ketosa 9. aldotetrosa Aldotetroasa adalah bentuk dari aldosa dengan 4 atom karbon yang mempunyai 4 bentuk isomes optis aktif sebagai berikut : HO O H H CH2OH L-Gliseraldehid C H C C H H O H OH OH HO HO C O H H H OH H C O H H C H O H OH H CH2OH L erithrosa OH HO CH2OH D triosa CH2OH L triosa CH2OH D erithrosa 9.3. Karbohidrat yang paling sederhana adalah 2.1.4.1. Aldosa yaitu karbohdrat yang mempunyai gugus alkanal. sedangkan ketosa adalah aldehid yang mempunyai gugus alkanon. 9.besar dari tiga. Struktur dari Aldopentosa adalah sebagai berikut : 107 .3 dihidroksi propanal (gliseral dehid).2.1. Secara garis besarnya kelompok karbohidrat adalah aldosa dan ketosa.1.

5.1.Aldopentoasa adalah bentuk dari aldosa dengan 5 atom karbon yang mempunyai 8 bentuk isomes optis aktif sebagai berikut : O C OH OH OH H H H CH2OH H H H H C O H OH OH OH CH2OH C H OH H O H OH H C OH H H OH O H OH OH H CH2OH CH2OH L Xylose O C H H H OH HO C O H OH H L ribose O C OH OH H H H OH CH2OH H D Ribose O C H H HO H OH OH H CH2OH D Xylose HO H H OH HO H CH2OH CH2OH L Arabinose D Lyxose L Lyxose D Arabinose 9. Struktur dari Aldoheksosa yang mempunyai 6 atom C dan 16 isomer optis aktif sebagai berikut : O O O O C H C H C H C H H H H H OH OH OH OH CH2OH HO HO HO HO H H H H CH2OH 108 HO HO HO H H H H H H H OH OH OH H CH2OH OH HO CH2OH .

D Allosa C H H HO H O H OH OH H OH CH2OH D Gulosa HO HO H HO L Allosa C O H H H OH H CH2OH L Gulosa HO HO H H D Talosa O C H H H H H L Talosa O C H OH OH H H CH2OH L Mannosa OH HO OH HO CH2OH D Mannosa C HO H HO HO O H H OH H H H HO H H C O H OH H OH OH HO H HO H O C H H H O C H OH H OH H CH2OH L Idosa OH HO H H OH HO CH2OH D Idosa CH2OH L Glukosa CH2OH D Glukosa C H HO HO O H OH H H HO H H C O H H OH OH 109 HO H H C O H H OH H HO C O H OH H H OH HO .

H OH CH2OH D Galaktosa HO H CH2OH L Galaktosa H OH HO CH2OH D Altrosa H CH2OH L Altrosa 9.2.2. Struktur dari Ketoheksosa yang mempunyai 6 atom C dengan 8 isomer optis aktif sebagai berikut CH2OH O H H H OH OH OH CH2OH HO HO HO CH2OH O H H H CH2OH 110 HO HO H CH2OH O H H H H CH2OH O OH OH H CH2OH OH HO CH2OH . Struktur dari Ketotetrosa yang mempunyai 4 atom C dengan 2 isomer sebagai berikut : CH2OH O H OH CH2OH D erithrulose berikut : HO CH2OH O H CH2OH L erithrulose 9.2.3.2. Struktur dari Ketopentosa yang mempunyai 5 atom C dengan 4 isomer optis aktif sebagai CH2OH O H H OH OH CH2OH D ribulose HO HO CH2OH O H H CH2OH L ribulose H HO CH2OH O OH HO H CH2OH D xylulose H CH2OH O H OH CH2OH L Xylulose 9.1.

Three common examples are sucrose.5.[2] and maltose. such as water. lactose. search A disaccharide or biose[1] is the carbohydrate formed when two monosaccharides undergo a condensation reaction which involves the elimination of a small molecule. 111 . Disaccharide From Wikipedia. 'Disaccharide' is one of the four chemical groupings of carbohydrates (monosaccharide.D psychose CH2OH O H HO H OH H OH HO H HO L psychose CH2OH O H OH H CH2OH L sorbose L tagatose CH2OH O HO H H H H D tagatose CH2OH O OH H H CH2OH L fructose OH HO OH HO CH2OH D fructose CH2OH D sorbose 9. disaccharides form an aqueous solution when dissolved in water.3. Like monosaccharides. disaccharide. from the functional groups only. oligosaccharide. Bentuk lingkar senyawa saccharida Bentuk lingkar pada senyawa saccharida terjadi bila atom C1 bergabung dengan gugus hidroksil pada atom C4 atau C5 sehingga terjadi bentuk senyawa lingkar furannosida atau pirannosida seperti berikut : CH2OH OH H H H OH H H OH H OH OH CH2OH CH2OH 9. the free encyclopedia Jump to: navigation. and polysaccharide).

Sucrose and trehalose are examples of non-reducing disaccharides. sometimes water-soluble. For example. cane sugar.[5] The two monosaccharides are bonded via a dehydration reaction (also called a condensation reaction or dehydration synthesis) that leads to the loss of a molecule of water and formation of a glycosidic bond. is made up of two glucose molecules. So. or saccharose) Lactulose Lactose (milk sugar) Maltose Trehalose Cellobiose Unit 1 glucose galactose galactose glucose glucose glucose Unit 2 fructose fructose glucose glucose glucose glucose Bond α(1→2)β β(1→4) β(1→4) α(1→4) α(1→1)α β(1→4) Maltose and cellobiose are hydrolysis products of the polysaccharides. still has a free hemiacetal unit. and sometimes sweet-tasting and sticky-feeling. even if both component sugars are the same (e.Classification There are two different types of disaccharides: reducing disaccharides. starch and cellulose. Cellobiose and maltose are examples of reducing disaccharides.or beta-) result in disaccharides that are diastereoisomers with different chemical and physical properties. respectively. Depending on the monosaccharide constituents. disaccharides are sometimes crystalline. milk sugar (lactose) is made from glucose and galactose whereas the sugar from sugar cane and sugar beets (sucrose) is made from glucose and fructose.. beet sugar. the reducing sugar. in which one monosaccharide. a process known as condensation. and non-reducing disaccharides.[citation needed] Properties The glycosidic bond can be formed between any hydroxyl group on the component monosaccharide. Common disaccharides Disaccharide Sucrose (table sugar. different bond combinations (regiochemistry) and stereochemistry (alpha.g. in which the components bond through an acetal linkage between their anomeric centers and neither monosaccharide has a free hemiacetal unit. Less common disaccharides include:[6] Disaccharide Kojibiose Nigerose Isomaltose Units two glucose monomers two glucose monomers two glucose monomers 112 Bond α(1→2) [7] α(1→3) α(1→6) . [3] [4] Formation Disaccharides are formed when two monosaccharides are joined together and a molecule of water is removed. glucose). Maltose. another notable disaccharide.

1. amylosa 9.6. Depending on the structure. Polysaccharides are often quite heterogeneous. α(1→4). α(1→3). ] two glucose monomers two glucose monomers two glucose monomers two glucose monomers two glucose monomers a glucose monomer and a fructose monomer a glucose monomer and a fructose monomer a glucose monomer and a fructose monomer a glucose monomer and a fructose monomer two mannose monomers β(1→1)β α(1→1)β[8] β(1→2) β(1→3) β(1→6) α(1→3) α(1→4) α(1→6) β(1→6) either α(1→2). the free encyclopedia Jump to: navigation.β-Trehalose Sophorose Laminaribiose Gentiobiose Turanose Maltulose Palatinose Gentiobiulose Mannobiose[disambiguation needed Melibiose Melibiulose Rutinose Rutinulose Xylobiose 9.7. 9. oligo saccharida. Polysaccharides are long carbohydrate molecules of repeated monomer units joined together by glycosidic bonds.[1][2] 113 . They may be amorphous or even insoluble in water.6. containing slight modifications of the repeating unit. a beta-glucan polysaccharide.β-Trehalose α.2. They range in structure from linear to highly branched. amilopektin 9. these macromolecules can have distinct properties from their monosaccharide building blocks. or α(1→6) a galactose monomer and a glucose α(1→6) monomer a galactose monomer and a fructose α(1→6) monomer a rhamnose monomer and a glucose α(1→6) monomer a rhamnose monomer and a fructose β(1→6) monomer two xylopyranose monomers β(1→4) From Wikipedia. search 3D structure of cellulose.6.β. poli saccharida.

the general formula can also be represented as (C6H10O5)n where 40≤n≤3000. being found in the form of both amylose and the branched amylopectin. In animals. Polysaccharides are composed of long chains of monosaccharide units bound together by glycosidic bonds. • Structure Natural saccharides are generally built of simple carbohydrates called monosaccharides with general formula (CH2O)n where n is three or more. Polysaccharides is an important class of biological polymers. an aldehyde or ketone with many hydroxyl groups added.or storage-related. and nitrocellulose.[6] It has many uses such as a significant role in the paper and textile industries.[3][4] Examples include storage polysaccharides such as starch and glycogen. increasing 114 . and is claimed to be the most abundant organic molecule on earth. Examples of monosaccharides are glucose.When all the monosaccharides in a polysaccharide are the same type. but when more than one type of monosaccharide is present they are called heteropolysaccharides or heteroglycans. Starch (a polymer of glucose) is used as a storage polysaccharide in plants. cellulose acetate. Polysaccharides have a general formula of Cx(H2O)y where x is usually a large number between 200 and 2500. and glyceraldehyde[5] Amylose is a linear polymer of glucose mainly linked with α(1→4) bonds. but has nitrogen-containing side branches. Considering that the repeating units in the polymer backbone are often six-carbon monosaccharides. celluloid. Glycogen's properties allow it to be metabolized more quickly. It is one of the two components of starch. Cellulose is used in the cell walls of plants and other organisms. Definitions of how large a carbohydrate must be to fall into the categories polysaccharides or oligosaccharides vary according to personal opinion. which suits the active lives of moving animals. that is. It can be made of several thousands of glucose units. fructose. and structural polysaccharides such as cellulose and chitin. Their function in living organisms is usually either structure. the polysaccharide is called a homopolysaccharide or homoglycan. Chitin has a similar structure. sometimes called 'animal starch'. and is used as a feedstock for the production of rayon (via the viscose process). Polysaccharides contain more than ten monosaccharide units. A typical monosaccharide has the structure H(CHOH)x(C=O)-(CHOH)y-H. the structurally similar glucose polymer is the more densely branched glycogen. the other being amylopectin. usually one on each carbon atom that is not part of the aldehyde or ketone functional group. Cellulose and chitin are examples of structural polysaccharides.

They can be digested by hydrolysis. rice. mannan. however. catalyzed by enzymes called amylases. and to change how other nutrients and chemicals are absorbed. Starches are insoluble in water. These carbohydrates types can be metabolized by some bacteria and protists. Potato. these carbohydrates enhance digestion among other benefits. once fermented in the colon. Even though these complex carbohydrates are not very digestible. fucoidan and galactomannan. The formations of starches are the ways that plants store glucose.its strength. the mechanism by which this occurs is unknown. Called dietary fiber. Many organisms can easily break down starches into glucose. arabinoxylan. The main action of dietary fiber is to change the nature of the contents of the gastrointestinal tract. wheat. Ruminants and termites. with regulatory authorities in many developed countries recommending increases in fiber intake. It also has multiple uses. It is found in arthropod exoskeletons and in the cell walls of some fungi. most organisms cannot metabolize cellulose or other polysaccharides like chitin and arabinoxylans. Polysaccharides also include callose or laminarin. and maize are major sources of starch in the human diet. they may comprise important dietary elements for humans. chrysolaminarin. Humans and other animals have amylases. Amylose consists of a linear chain of several hundred glucose molecules and Amylopectin is a branched molecule made of several thousand glucose units (every chain of 24–30 glucose units is one unit of Amylopectin).[10] Not yet formally proposed as an essential macronutrient.[9] Soluble fiber also attenuates the absorption of sugar. use microorganisms to process cellulose. It is made up of a mixture of amylose (15–20%) and amylopectin (80–85%). dietary fiber is nevertheless regarded as important for the diet. Function Nutrition Polysaccharides are common sources of energy. Although insoluble fiber is associated with reduced diabetes risk. making them less likely to enter the body. which can break the alpha-linkages (glycosidic bonds). so they can digest starches.[7][8] Soluble fiber binds to bile acids in the small intestine. 115 . for example. normalizes blood lipid levels and. including surgical threads. this in turn lowers cholesterol levels in the blood. reduces sugar response after eating.[7][8][11][12] Storage polysaccharides Starches Starches are glucose polymers in which glucopyranose units are bonded by alpha-linkages. produces short-chain fatty acids as byproducts with wide-ranging physiological activities (discussion below). xylan.

but one that is less compact than the energy reserves of triglycerides (lipids). The entire globular granule may contain approximately 30.[13] A view of the atomic structure of a single branched strand of glucose units in a glycogen molecule. Glycogen forms an energy reserve that can be quickly mobilized to meet a sudden need for glucose. Glycogen serves as the secondary long-term energy storage in animal and fungal cells. but can also be made by glycogenesis within the brain and stomach. having a similar structure to amylopectin but more extensively branched and compact than starch. A core protein of glycogenin is surrounded by branches of glucose units. with the primary energy stores being held in adipose tissue.000 glucose units. Glycogen is a polymer of α(1→4) glycosidic bonds linked. 116 . and is sometimes referred to as animal starch. and plays an important role in the glucose cycle.[14] Glycogen is the analogue of starch. a glucose polymer in plants. Glycogen is found in the form of granules in the cytosol/cytoplasm in many cell types. with α(1→6)linked branches.Glycogen Schematic 2-D cross-sectional view of glycogen. Glycogen is made primarily by the liver and the muscles.

It is stored in liver and muscles. and red blood cells[16][17][18]—mostly depends on physical training. Wood is largely cellulose and lignin. However. such as exoskeletons. • • • • It is an energy reserve for animals. On hydrolysis. It also yields glucose on hydrolysis.[15] Only the glycogen stored in the liver can be made accessible to other organs. glycogen is found in a low concentration (one to two percent of the muscle mass). The uterus also stores glycogen during pregnancy to nourish the embryo.In the liver hepatocytes. Chemically. chitin is closely related to chitosan (a more water-soluble derivative of chitin). so they do not digest cellulose. basal metabolic rate. Certain animals such as termites can digest cellulose. It is also closely related to cellulose in that it is a long unbranched chain of glucose derivatives.4-linked α-D-galactosyluronic acid residues. They are present in most primary cell walls and in the non-woody parts of terrestrial plants. It turns red when mixed with iodine. glycogen can compose up to eight percent of the fresh weight (100–120 g in an adult) soon after a meal. and produced by some plants. It is the most abundant carbohydrate in nature. it yields glucose. 117 . because bacteria possessing the enzyme are present in their gut. Cellulose is a polymer made with repeated glucose units bonded together by beta-linkages. and eating habits such as intermittent fasting. Cellulose The structural component of plants are formed primarily from cellulose. Some of these microorganisms have receptors to simple sugars from the decomposition of chitin. the amount of glycogen stored in the body—especially within the muscles. Both materials contribute structure and strength. It does not change color when mixed with iodine. secreted by microorganisms such as bacteria and fungi. It is insoluble in water. Small amounts of glycogen are found in the kidneys. It forms a structural component of many animals. It is the chief form of carbohydrate stored in animal body. If chitin is detected. protecting the organism. and even smaller amounts in certain glial cells in the brain and white blood cells. Chitin Chitin is one of many naturally occurring polymers. while paper and cotton are nearly pure cellulose. Structural polysaccharides Arabinoxylans Arabinoxylans are found in both the primary and secondary cell walls of plants and are the copolymers of two pentose sugars: arabinose and xylose. liver. Its breakdown may be catalyzed by enzymes called chitinases. In the muscles. Humans and many other animals lack an enzyme to break the beta-linkages. Over time it is bio-degradable in the natural environment. they then produce enzymes to digest it by cleaving the glycosidic bonds in order to convert it to simple sugars and ammonia. Pectins Pectins are a family of complex polysaccharides that contain 1.[15] Glycogen is composed of a branched chain of glucose residues. Cellulose is insoluble in water.

There is enormous structural diversity.[19] Polysaccharide biosynthesis is a tightly regulated. Poly-Nacetylglucosamine in S. including fungi and algae. capsules and exopolysaccharides. and have molecular weights on the order of 100-1000 kDa.. This "capsule" cloaks antigenic proteins on the bacterial surface that would otherwise provoke an immune response and thereby lead to the destruction of the bacteria. such as when wiped.g. They are linear and consist of regularly repeating subunits of one to six monosaccharides. polymer modification and synthesis. and the external ecological functions is a huge area of research. peptidoglycan). Capsular polysaccharides are water soluble.[20][21] Bacterial capsular polysaccharides Pathogenic bacteria commonly produce a thick. coli alone.. welan gum. cleaners and paints. layer of polysaccharide. poured or brushed. commonly acidic. new antibiotics and vaccines) and the commercial exploitation to develop novel applications. and important virulence factors (e. gellan gum. Pseudomonas aeruginosa in the human lung). mucous-like.g. either conjugated or native are used as vaccines. Mixtures of capsular polysaccharides. to permitting the bacterium to survive in harsh environments (e. aureus). often secrete polysaccharides as an evolutionary adaptation to help them adhere to surfaces and to prevent them from drying out. Humans have developed some of these polysaccharides into useful products. phosphate groups and/or sulfuric ester groups.. lipopolysaccharides. but fluidity when the slightest shear is applied.g. The potential benefits are enormous and should enable for example the development of novel antibacterial strategies (e. dextran. This property is referred to as pseudoplasticity.3 0. like lotions. a viscous appearance when stationary. Bacterial polysaccharides Bacterial polysaccharides represent a diverse range of macromolecules that include peptidoglycan. diutan gum and pullulan.5 23330 16000 118 . Bacteria and many other microbes. nearly two hundred different polysaccharides are produced by E. Most of these polysaccharides exhibit interesting and very useful visco-elastic properties when dissolved in water at very low levels. for example. or shear thinning. Viscosity of Welan gum Shear Rate (rpm) Viscosity (cP) 0. energy-intensive process and understanding the subtle interplay between the regulation and energy conservation..Acidic polysaccharides Acidic polysaccharides are polysaccharides that contain carboxyl groups. compounds whose functions range from structural cell-wall components (e.g. including xanthan gum.[22] This gives many foods and various liquid consumer products.

1 2 4 5 10 20 50 100 11000 5500 3250 2900 1700 900 520 310 Aqueous solutions of the polysaccharide alone have a curious behavior when stirred. returning to their relaxed state. is a recent focus of research by several groups and it has been shown to be important for adhesion and invasion during bacterial infection. the swirl continues due to momentum.[23] The exopolysaccharide alginate is a linear copolymer of β-1. as it plays a key structural role in outer membrane integrity. particularly of pilin and flagellin. and then reverses direction briefly. These polysaccharides are synthesized from nucleotide-activated precursors (called nucleotide sugars) and. The pel and psl loci are two recently discovered gene clusters that also encode exopolysaccharides found to be important for biofilm formation. and is responsible for the mucoid phenotype of late-stage cystic fibrosis disease. all the enzymes necessary for biosynthesis. Cell-surface polysaccharides play diverse roles in bacterial ecology and physiology. mediate host-pathogen interactions. Rhamnolipid is a biosurfactant whose production is tightly regulated at the transcriptional level. as well as being an important mediator of host-pathogen interactions. The enzymes that make the A-band (homopolymeric) and B-band (heteropolymeric) O-antigens have been identified and the metabolic pathways defined. This recoil demonstrates the elastic effect of the polysaccharide chains previously streched in solution. but the precise role that it plays in disease is not well understood at present. [24] 119 . They serve as a barrier between the cell wall and the environment.4-linked D-mannuronic acid and L-guluronic acid residues. and form structural components of biofilms. Protein glycosylation. in most cases. then stops. assembly and transport of the completed polymer are encoded by genes organized in dedicated clusters within the genome of the organism. After stopping. Lipopolysaccharide is one of the most important cellsurface polysaccharides.

hemiselulosa 9.8. konformasi heksosa ada dua yaitu : a.7.9.1. selulosa 9. konformasi kursi H O CH2OH H OH H b.2. Konformasi sampan H O CH2OH O H H n OH O OH H OH O H n Beberapa reaksi karbohidrat dengan perekasi kimia adalah sebagai berikut : C (H O H + H3CI/Ag2O --------------OH)n H3COCH ( HCOCH3)n-1 CH2OCH3 O CH2OH O 120 .7.

C (H H + Ac2O --------------OH)n Ac-OCH ( HCOAc)n-1 CH2OAc O CH2OH C (H O H + ROH/H OH)n + --------------- ROCH ( HCOH)n-1 CH2OH O CH2OH C (H O H + NaBH4 OH)n --------------(H CH2OH OH)n CH2OH CH2OH C (H O H + Br2/H2O --------------OH)n COOH ( HCOH)n CH2OH CH2OH O H + HNO3 (H OH)n CH2OH -------------- C COOH ( HCOH)n COOH C (H O H + HCN/H2O + Na(Hg) -----OH)n O C-H ( H OH) (HCOH)n CH2OCH3 CH2OH 121 .

1.0 Isoleusin Ile (I) 131 6.4 Asparagin Asn (N) Cysteine Cys (C) 121 5. ASAM AMINO DAN PROTEIN 10.0 5.1. Klassifikasi asam amino 10. Asam amino netral Nama Alanin Ringkasan Ala (A) BM 89 132 Struktur H3C-CH-COOH NH2 H3N.0 Leusin Leu (L) 131 6.0 .C-CH2-CH2CH-COOH O NH2 CH2-COOH NH2 H3C-CH2-CH(CH3)-CH-COOH NH2 (H3C)2CH-CH2-CH-COOH 122 Titik isoelektrik 6.1.C-CH2-CH-COOH O NH2 HS-CH2-CH-COOH NH2 H3C.0 Glutamine Gln (Q) 146 5.C (H O H + H2NOH/Ac2O/NaOCH3 --OH)n ( O C-H (HCOH)n-1 CH2OH CH2OH MODUL X X.7 Glycine Gly (G) 75 6.

0 .NH2 Methionine Met(M) 149 H3C-S-CH2-CH2-CH-COOH NH2 C6H5-H2C-CH-COOH NH2 5.7 Valine Val (V) 117 6.3.1.5 5.7 Threonine Thr (T) 119 6. Asam amino basa Arginine Arg (R 174 H2N.0 10.0 Glutamic Glu (E)147 HOOC-CH2 -H2C-CH-COOH NH2 10.3 Serine Ser (S) 105 5.9 Tyrosine Tyr (Y) 181 5.7 Phenylalanine Phe (F) 165 Proline Pro (P) 115 H2C-CH-COOH NH HO-H2C-CH-COOH NH2 H3C-CHOHCH-COOH NH2 6.1.C-NH-(H2C)3-CH-COOH NH NH2 123 6.0 Trypthophan Trp (W) 204 N CH2-CH-COOH NH2 p-OH-C6H4H2C-CH-COOH NH2 (H3C)2CH-CH-COOH NH2 5. Asam amino asam Aspartic Asp (D) 133 HOOC-CH2-CH-COOH NH2 3.2 3.2.

2.RCHNH2-COOH 10.0 Lysine Lys (K) 146 6.2.0 10.2.Histidine his (H) 155 N N H2C-CH-COOH NH2 H2N. sintesa asam amino dengan alkanonoat RCOCOOH + NH3 + NaBH4 ------------------.H2NRCHCOOH 10.1.2. sintesa asam amino dengan dietil asetamidomalonat H3CCONHCH(CO2C2H5)2 + RX + H3O+ + NaOC2H5 ---------------.RCHBr-COOH + NH3 -----.4.(H2C)4-CH-COOH NH2 6.RCHNH2-COOH + HBr 10. sintesa asam amino dengan pereaksi posfohalida R-CHOH-COOH + PBr3 ---------------.3.RCHNH2COOH 10.R-CHNH2-CO-NH-COOH + H-O-H CH R’ Blocking Gugus -NH2 Pada asam amino dari reaksi sintesa protein {(H3C)3COCO}2O Ditert-butil dikarbonat 124 . Ikatan peptide ikatan peptide adalah ikatan yang terjadi akibat reaksi dehidrolisa gugus -NH2 dan -COOH dari beberapa asam amino membentuk molekul protein sebagai berikut : R-CHNH2-COOH + R’CHNHH-COOH ----------.2.3. sintesa asam amino 10. sintesa asam amino dengan asam sianida dalam suasana asam RCHO + HCN + H3O+ + NH4Cl---------------------.

ester gliserida. tanduk jaringan penghubung elastis sumber H3COH PhCH2OH Klassifikasi protein konyugasi ( protein yang mengandung senyawa selain asam amino seperti karbohidrat. kulit. Struktur protein struktur protein tersusun dari ikatan peptida primer. urat rambut.4. asam nukleat. sekunder. kolesterol 125 80 karbohidrat karbohidrat karbohidrat 10 17 20 non asam amino Σ−nonasam amino (%) . kuku. dan kuartener membentuk rantai α helik seperti jalinan talitemali contoh protein angiotensin II yang terdapat dalam plasma darah H2N-D-R-V-Y-I-H-P-F-COOH Klassifikasi protein berdasarkan konformasinya Protein Fibrous protein Kolagen αkeratin Elastin Potein globuler Insulin Lysozyme Ribonuklease Albumin Immunoglobulin Myoglobulin hormone kontrol metabolisme glukosa enzim hidrolitik enzim control sintesa RNA protein menggumpal oleh panas immune respon oksigen transport jaringan penghubung. Protein Glycoprotein γ-Globulin Karboksipeptidase Interferon Lipoprotein Plasma β-lipoprotein lemak. tertier.Blocking Gugus -COOH Pada asam amino dari reaksi sintesa protein 10.

3 ester posfat 4 RNA RNA 60 5 . ESTER TRIGLISERIDA(lipid) Ester gliserida adalah senyawa molekul organic yang didapatkan dialam dipisahkan dari sel dan jaringan biota dengan cara ekstraksi dengan pelarut organic non polar. Lipid lebih ditentukan oleh sifat fisikanya dari pada sifat kelarutannya sebagaimana halnya dengan karbohidrat dan protein. Struktur ester gliserida adalah sebagai berikut : CH2-O-CO-R CH-O-CO-R CH2-O-CO-R Berdasarkan konfigurasi ikatan asam lemak pada gliserol ada 4 konfigurasi yaitu : CH2-O-CO-R CH-O-CO-R 126 FeO Fe 23 0. Ester gliserida tersusun dari gliserol atau alkanol berberat molekul besar dengan asam lemak.Nucleoprotein Ribosomal protein Virus tembakau Posfoprotein Casein Metallo protein Ferritin Hemoglobin Struktur insulin 21 asama amino rantai I H2N-G-I-V-E-Q-C-C-T-S-I-C-S-L-Y-Q-L-E-N-Y-C-N-OH 30 asam amino rantai II H2N-F-V-N-E-H-L-C-G-S-H-L-V-E-A-L-Y-L-V-C-G-E-R-G-F-F-Y-Y-P-L-Y-OH MODUL X. Lipid biasanya terdiri dari atom karbon yang banyak dalam strukturnya yang larut dalam pelarut organic non polar dan tak larut dalam air. dan lipid sederhana yang tidak dapat dihidrolisa seperti kolesterol dan steroid lainnya. XI. Ester gliserida dapat digolongkan menjadi 2 golongan besar yakni lipid kompleks seperti lemak dan lilin yang mengandung ikatan ester dan dapat dihidrolisa menjadi molekul kecil.

CH2-O-CO-R Lurus CH2-O-CO-R RO-CO-C-H CH2-O-CO-R Garpu R-OC-O-CH2 CH-O-CO-R CH2-O-CO-R Kursi CH2-O-CO-R CH-O-CO-R R-OC-O-CH2 topi Jika lipid dihidrolisa akan terurai menjadi gliserol dan asam-asam lemak CH2-O-CO-R CH-O-CO-R’ CH2-O-CO-R” Ester gliserida 11. Klassifikasi ester gliserida CH2OH + 3H3O+ -----------------. lemak adalah asam lemak jenuh dengan gliserol membentuk ester CH2-O-CO-R CH-O-CO-R 127 .CH-OH CH2OH gliserol RCOOH + R’COOH R”COOH asam lemak a. minyak adalah asam lemak tak jenuh dan jenuh berikatan dengan gliserol membentuk ester CH2-O-CO-R CH-O-CO-R CH2-O-CO-(HC=CH)nR b. 1.

cephlin (otak) CH2-O-CO-R R-COO-C-H CH2-O-PO3-CH2-CH2-N+H3 . posfolipid adalah asam lemak dan senyawa basa posfolipid membentuk ester .L Lecitin (kuning telor) CH2-O-CO-R R-COO-C-H CH2-O-PO3-CH2-CH2-N+(CH3)3 .CH2-O-CO-R c.sphingomyelin CH2-OPO3-CH2-CH2-N+(CH3)3 CH-NH-CO-(CH2)16-24-CH3 CH-OH CH=CH(CH2)12CH3 d. malam adalah asam lemak berberat molekul besar dengan alkanol berberat molekul besar CH3(CH2)20-24-COO-(CH2)27CH3 Lilin lebah Jenis-jenis asam lemak Nama Asam lamak jenuh 128 struktur BP (oC) .sphingosin CH2-OH CH-NH2 CH-OH CH=CH(CH2)12CH3 .

cis) H3C-(CH2)4-(CH2-HC=CH)4-(CH2)2-COOH (cis4x) 32 44 58 63 70 75 4 -5 -11 -50 Komposis (%) asam lemak pada berbagai sumber bahan alami Asam lemak jenuh Sumber Hewan Lemak babi Butter Lemak manusia Lemak ikan paus Tumbuhan Kelapa Jagung Zaitun Kacang tanah Biji bunga matahari Biji jarak 50 18 1 1 8 10 5 7 5 2 4 5 5 3 1 6 35 80 60 20 8 85 1 45 7 20 20 4 50 2 1 1 10 3 8 25 25 25 12 15 10 8 3 50 25 46 35 6 5 10 10 1 L M P S asam lamak tak jenuh O R Li Lin Reaksi sintesa ester gliserida a.Laurat Mirisitat Palmitat Stearat Arachidat Asam lemak tak jenuh Palmitoleat Oleat Ricinileat Linoleat Linolenat Arachidonat H3C-(CH2)10-COOH H3C-(CH2)12-COOH H3C-(CH2)14-COOH H3C-(CH2)16-COOH H3C-(CH2)10-COOH H3C-(CH2)5HC=CH-(CH2)7-COOH H3C-(CH2)7HC=CH-(CH2)7-COOH H3C-(CH2)5CHOH-CH2-HC=CH-(CH2)7-COOH (cis) 5 H3C-(CH2)3-(CH2-HC=CH)2-(CH2)7-COOH (cis.cis.cis) H3C-(CH2-HC=CH-)3-(CH2)7-COOH (cis. RCOOH + OHCH2-CHOH-CH2OH 129 ROOCH2-CHCOOR-CH2COOR .

H+ H3C-HOH-CH2-CO-SACP Enoyl ACP dehidrase H3C-CH=CH-CO-SACP NADPH 130 + CO2 + HSCoA . HSACP HOOC-CH2-CO-SACP H3C-CO-CH2-CO-SACP NADPH.H3CO-S-synthetase + HOOC-CH2CO-S-ACP H3C-CO H-C-CO-S-ACP COOH H3C-CO-CH2-CO-S-ACP + CO2 Asetoasetil ACP (acyl carrier protein) Biosintesa lipid H3C-CO-SCoA Asetil CoA ACP transferase HS-ACP H3C-CO-SACP β KetoACP transferase H3C-CO-SSynthetase β Keto ACP synthetase Asetil CoAcarboksilase CO2 HOOC-CH2-CO-SCoA Malonil CoA ACP transferase.

a Purine alkaloid 131 . tumbuhan. Contohnya adalah anestesi lokal dan kokain stimulan. seperti narkoba. dengan pH alkali dan tindakan fisiologis yang ditandai pada fisiologi hewan [kutipan diperlukan]. kafein stimulan. ada pengecualian untuk masing-masing kriteria. atau kina obat antimalaria. nikotin. termasuk bakteri. Mereka sering memiliki efek farmakologis dan digunakan sebagai obat. Caffeine. Banyak alkaloid dapat dimurnikan dari ekstrak mentah oleh ekstraksi asam-basa. Banyak alkaloid yang beracun bagi organisme lain. atau dalam ritual entheogenic. Alkaloid dihasilkan oleh berbagai macam organisme. Alkaloid yang paling memiliki rasa pahit. Namun. morfin analgesik. dan hewan dan merupakan bagian dari kelompok produk alami (juga disebut metabolit sekunder).H3C-CH2-CH2-CO-SACP berulang MODUL XI ALKALOID Struktur kimia dari efedrin. jamur. sebuah alkaloid phenethylamine Alkaloid adalah senyawa alami kimia yang mengandung atom nitrogen dasar [1] Nama ini berasal dari kata basa dan digunakan untuk menggambarkan setiap basa nitrogen yang mengandung dan senyawa organik dengan satu atau lebih dari fitur berikut:. Senyawa heterosiklik yang mengandung nitrogen.

dopamine Indole group: o Tryptamines: serotonin. hydrastine. dihydroquinidine. guvacine. dapat dikelompokkan berdasarkan kemiripan struktur dengan senyawa yang diketahui. cocaine. serta asal biogenetis mana dikenal [2] [3]. ergotamine. nicotine. theophylline Terpenoid group: o Aconitum alkaloids: aconitine o Steroid alkaloids (containing a steroid skeleton in a nitrogen containing structure):  Solanum (e. anabasine. dihydroquinine. bufotenine. voacangine. pelletierine. asal biologisnya. coniine. brucine. DMT. narceine). di mana jalur biosintesis alkaloid yang tidak diketahui. quinidine. lobeline. 7-hydroxymitragynine o Tabernanthe iboga alkaloids: ibogaine. trigonelline. [3] • • • • • • • • • • • Pyridine group: piperine. ecgonine. tetrahydroharmine o Yohimbans: reserpine. sebuah alkaloid Chemotheraputic terisolasi dari Madagaskar periwinkle • Alkaloid classifications Klasifikasi dari alkaloid adalah kompleks dan dapat dipandu oleh seperangkat aturan yang mempertimbangkan struktur dan fitur kimia lainnya dari molekul alkaloid. Sebagai contoh. theobromine. swainsonine Quinoline group: quinine. nicotine Tropane group: atropine. 5-MeO-DMT. brucine Purine group: o Xanthines: caffeine. Pyrrolidine group: hygrine. yohimbine o Vinca alkaloids: vinblastine. ephedrine. sparteine. solanine. coronaridine o Strychnos nux-vomica alkaloids: strychnine. berbamine. emetine. vincristine o Kratom (Mitragyna speciosa) alkaloids: mitragynine. sanguinarine. cevadine Isoquinoline group: opium alkaloids (papaverine. arecaidine. oripavine) Phenethylamine group: mescaline.Struktur kimia Vinblastine. codeine. thebaine. scopolamine. strychnine. atau dengan organisme (s) dari yang alkaloid yang diisolasi. lysergic acid o Beta-carbolines: harmine. psilocybin o Ergolines (the ergot alkaloids): ergine. cytisine. potato and tomato) alkaloids (solanidine. catuabine Indolizine group: senecionine. cuscohygrine. oxyacanthine Phenanthrene alkaloids: opium alkaloids (morphine. chaconine) 132 . arecoline. veratrine. harmaline. termasuk non-nitrogen senyawa. berberine. pancratistatin. narcotine.g.

phytolaccotoxin  MODUL XII XII. monoterpen adalah gabaungan 2 molekul isoprena konfigurasi isoprena pada monoterpen ada 4 kombinasi : Isoprena Belakang belakang - Belakang depan - Depan belakang 133 . jervine. choline.• • Veratrum alkaloids (veratramine. neurine Miscellaneous: capsaicin. cynarin. muldamine)[4]  Fire Salamander alkaloids (samandarin)  Others: conessine Quaternary ammonium compounds: muscarine. cyclopamine. cycloposine. TERPENOID Terpenoid adalah senyawa organic yang terdiri dari rantai isoprene mulai dari 10 dengan kelipatan 5 atom karbon Klassifikasi terpenoid a. phytolaccine.

-

Depan depan

b. sesquiterpen c. diterpen d. sesterterpen e. triterpen f. tetraterpen Reaksi sintesa terpenoid

3 molekul isoprene 4 molekul isoprene 5 molekul isoprene 6 molekul isoprene 8 molekul isoprene

jumlah atom C = 15 jumlah atom C = 20 jumlah atom C = 25 jumlah atom C = 30 jumlah atom C = 40

OPP + IPP DAPP

OPP

OPP

CH2OH Geraniol GPP

CH2OPP

CH2OPP

CH2OPP + GeraniolPP nerolPP 134 limonen

CH2OPP + GPP

CH2OPP

CH2OPP + -:OPP

CH2OPP Farnesol piroposfat

CH2OH Farnesol

CH2OPP Farnesol piroposfat + 135

o Farnesol piroposfat

CH2OPP

squalena

MODUL XIII XIII. STEROID

Steroid
From Wikipedia, the free encyclopedia

Jump to: navigation, search This article is about the chemical family of lipids. For the performance-enhancing substance, see Anabolic steroid.

IUPAC recommended ring lettering (left) and atom numbering (right) of the steroid skeleton.[1][2] The four rings A-D form a sterane core.

136

lanosterol dan cycloartenol. Dalam bahasa populer. berasal dari siklisasi dari squalene triterpene. Ratusan steroid yang berbeda ditemukan pada tumbuhan. Inti adalah struktur karbon dari empat cincin leburan: tiga cincin sikloheksana dan satu cincin cyclopentane. ♣ Kortikosteroid meliputi glukokortikoid dan mineralokortikoid. [3] Sterol adalah bentuk khusus dari steroid. dengan kelompok hidroksil pada atom C-3 dan kerangka berasal dari kolestan [2] Kolesterol adalah salah satu sterol yang paling dikenal. hewan. yang memodulasi fluiditas membran sel dan merupakan konstituen utama dari 137 . Ada steroid anabolik alami dan sintetis. The total number of carbons (30) reflects its triterpenoid origin. Kebanyakan medis 'steroid' obat kortikosteroid. ♣ Kolesterol. Sebuah steroid merupakan lipid terpenoid dicirikan oleh inti sterane dan kelompok fungsional tambahan. Glukokortikoid mengatur banyak aspek metabolisme dan fungsi kekebalan tubuh. sedangkan mineralokortikoid membantu mempertahankan volume darah dan mengontrol ekskresi ginjal elektrolit. estrogen. Kedua. dan jamur. . dan progestagens. ♣ Anabolic steroids adalah kelas steroid yang berinteraksi dengan reseptor androgen untuk meningkatkan otot dan sintesis tulang. Steroid bervariasi oleh kelompok-kelompok fungsional yang melekat pada cincin ini dan keadaan oksidasi dari cincin.Stick model of the steroid lanosterol. Mereka termasuk androgen. • • Klasifikasi Taksonomi / Fungsional Beberapa kategori umum dari steroid: • Hewan steroid o steroid Serangga ♣ Ecdysteroids seperti ecdysterone o Vertebrata steroid ♣ steroid hormon ♣ steroid Seks adalah subset dari hormon seks yang menghasilkan perbedaan seks atau reproduksi dukungan.. kata "steroid" biasanya mengacu pada steroid anabolik. Semua steroid yang dibuat dalam sel baik dari lanosterol sterol (hewan dan jamur) atau cycloartenol (tanaman).

dan testosteron di testis. Contoh dari klasifikasi ini meliputi: Class Cholstanes Cholanes Examples cholesterol cholic acid Number of carbon atoms 27 24 21 19 18 Pregnanes progesterone Androstanes testosterone Estranes estradiol Gonane (or steroid nucleus) is the hypothetic parent (17-carbon tetracyclic) hydrocarbon molecule without any alkyl sidechains. dan testosteron. baik de novo atau dari sumber perifer yang diturunkan. Estrogen dan progesteron yang dibuat terutama di ovarium dan plasenta selama kehamilan. Neuron tertentu dan glia pada sistem saraf pusat (SSP) mengekspresikan enzim yang diperlukan untuk sintesis lokal neurosteroids pregnane. progesteron. Tingkat membatasi langkah sintesis steroid adalah konversi kolesterol menjadi pregnenolon. yang terjadi di dalam mitokondria New! Click the words above to edit and view alternate tra 138 . Testosteron juga diubah menjadi estrogen untuk mengatur pasokan masing-masing. Salah satu contoh betapa MESH melakukan klasifikasi ini tersedia di katalog MESH Wikipedia. kortisol. • Tanaman steroid o Phytosterols o Brassinosteroids • Jamur steroid o ergosterol Structural struktural Hal ini juga memungkinkan untuk mengklasifikasikan steroid berdasarkan komposisi kimianya. dalam tubuh baik wanita dan pria.plak terlibat dalam aterosklerosis.[4] Metabolism Steroid meliputi estrogen.

steroid pertama dalam jalur. squalene dan. membuat jalur target umum untuk antibiotik dan obat anti infeksi. Selain itu. Jalur metabolik meliputi: • steroid sintesis . steroid pertama.yang interkonversi dari berbagai jenis steroid • steroid degradasi. Jalur ini dilakukan dengan cara yang berbeda pada hewan daripada di banyak organisme lain. Steroid biosynthesis Biosintesis steroid merupakan jalur metabolisme yang menghasilkan steroid anabolik dari prekursor sederhana. Dimulai di jalur mevalonate pada manusia. memodifikasi dan mengkonsumsi steroid.pembuatan steroid dari prekursor sederhana • steroidogenesis . dimana isopentenil intermediet pirofosfat (IPP) dan pirofosfat dimethylallyl (DMAPP) bentuk geranyl pirofosfat (GPP). DMAPP dan IPP bentuk lanosterol. dengan Asetil-KoA sebagai blok bangunan yang membentuk DMAPP dan IPP [6]. Modifikasi lebih lanjut milik steroidogenesis berhasil Mevalonate pathway 139 . akhirnya. Metabolisme steroid adalah set lengkap reaksi kimia dalam organisme yang memproduksi. metabolisme steroid pada manusia merupakan target dari obat penurun kolesterol seperti statin.• Sederhana versi dari bagian akhir jalur sintesis steroid. Beberapa intermediet dihilangkan untuk kejelasan. lanosterol. Dalam langkah-langkah berikut.

Sensor intraseluler mendeteksi kadar kolesterol rendah dan merangsang produksi endogen oleh jalur HMG-CoA. degradasi reduktase dan fosforilasi Farmakologi Sejumlah obat menargetkan jalur mevalonate: • Statin (digunakan untuk kadar kolesterol tinggi) • Bifosfonat (digunakan dalam pengobatan berbagai penyakit degeneratif tulang) Tanaman dan bakteri Pada tumbuhan dan bakteri. yang dirakit dan dimodifikasi untuk terpene bentuk dan isoprenoidnya [8].Mevalonate pathway Main article: Mevalonate pathway The mevalonate pathway or HMG-CoA reductase pathway starts with and ends with dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). dan membentuk kelas terbesar produk tanaman alami. serta meningkatkan penyerapan lipoprotein dengan up-mengatur reseptor LDL. yang adalah kelas besar lipid yang mencakup karotenoid. Peraturan jalur ini juga dicapai dengan mengendalikan laju terjemahan dari mRNA. [7] [8] DMAPP untuk lanosterol Pirofosfat dan isopentenil pirofosfat dimethylallyl menyumbangkan unit isoprena. [9] Di sini. [10] [11] 140 . jalur non-mevalonate menggunakan piruvat dan gliseraldehida 3-fosfat sebagai substrat. unit isoprena bergabung bersama untuk membuat squalene dan kemudian dilipat dan dibentuk menjadi satu set cincin untuk membuat lanosterol [10]. Peraturan dan umpan balik Beberapa enzim kunci dapat diaktifkan melalui regulasi transkripsi DNA pada aktivasi SREBP (Sterol Peraturan Elemen-Binding Protein-1 dan -2). Lanosterol kemudian dapat diubah menjadi steroid lain seperti kolesterol dan ergosterol.

namun jalur dari steroidogenesis manusia diperlihatkan pada gambar. tetapi tidak untuk produksi senyawa tersebut di laboratorium kimia). Produk dari steroidogenesis meliputi: • androgen 141 .Human Steroidogenesis steroidogenesis Steroidogenesis adalah proses dimana bentuk yang diinginkan dari steroid yang dihasilkan oleh transformasi steroid lainnya (Pembentukan steroid. Jalur dari steroidogenesis dapat berbeda dari organisme ke organisme. umumnya mengacu pada sintesis biologis hormon steroid.

search Molecular structure of the flavone backbone (2-phenyl-1.4-benzopyrone) Isoflavan structure Neoflavonoids structure 142 . |FLAVONOID Jump to: navigation. [12] Asam empedu kemudian dapat dieliminasi melalui sekresi dari hati dalam empedu. seperti CYP3A4. untuk membentuk asam empedu sebagai produk akhir. Reaksi-reaksi memperkenalkan oksigen ke dalam cincin steroid dan memungkinkan struktur untuk dipecah oleh enzim lainnya.o testosteron • estrogen dan progesteron • corticoids o kortisol o aldosteron Elimination Steroid terutama dioksidasi oleh sitokrom P450 oksidase enzim. [13] ekspresi gen ini oksidase dapat diregulasi oleh PXR sensor steroid ketika ada konsentrasi darah tinggi steroid [14] MODUL XIV XIV.

. flavan-3-OLS. dan kedelai. adalah kelas metabolit sekunder tanaman. Flavonoid disekresikan oleh akar tanaman inang mereka rhizobia membantu dalam tahap infeksi hubungan simbiosis dengan kacang-kacangan seperti kacang polong. atau katekin (catechin meskipun sebenarnya subkelompok flavonoid). kacang-kacangan.4-benzopyrone) struktur • neoflavonoids. Flavonol. anti-mikroba [6] dan aktivitas anti-kanker New! Click the words above to edit and view alternate translations. rutin). [2] mereka dapat diklasifikasikan menjadi: • flavonoid. Menurut tata nama IUPAC. dan dengan demikian. Hidup rhizobia dalam tanah dapat merasakan flavonoid dan ini memicu sekresi faktor Nod. juga ditemukan ubiquitously. anti-inflamasi [5].Flavonoid (atau bioflavonoid). bioflavonoid asli seperti quercetin. berasal dari 4-phenylcoumarine (4-fenil-1 . berbagai mereka dan toksisitas relatif rendah dibandingkan dengan senyawa tanaman aktif (alkaloid misalnya) berarti bahwa banyak hewan. jamur [3] dan serangga. Mereka menunjukkan antialergi. virus. flavonoid dan flavonol. Di 143 . [edit] Biological activity Flavonoid (khususnya flavonoid seperti katekin) adalah "kelompok yang paling umum dari senyawa polifenol dalam makanan manusia dan ditemukan ubiquitously pada tanaman" [4]. Kelas ini adalah yang pertama yang akan disebut "bioflavonoid. dan karsinogen. berasal dari 2-phenylchromen-4-satu (2-fenil-1 . yang pada gilirannya diakui oleh tanaman inang dan dapat menyebabkan akar rambut deformasi dan tanggapan selular beberapa seperti fluks ion dan pembentukan bintil akar . Tiga kelas flavonoid di atas adalah semua keton yang mengandung senyawa. Mereka juga melindungi tanaman dari serangan mikroba.4-benzopyrone) struktur (contoh: quercetin. berasal dari 3-phenylchromen-4-satu (3-fenil-1 . tetapi lebih rendah kuantitas." Para flavonoid Ketentuan dan bioflavonoid juga telah lebih longgar digunakan untuk menggambarkan senyawa polihidroksi non-keton polifenol yang lebih khusus disebut flavonoid. Flavonoid telah disebut sebagai "pengubah respon biologi alami" karena bukti eksperimental yang kuat kemampuan melekat mereka untuk memodifikasi reaksi tubuh terhadap alergen. • isoflavonoid. termasuk manusia. • [edit] Biosynthesis Main article: Flavonoid biosynthesis [edit] Biological roles Flavonoid tersebar luas pada tanaman memenuhi banyak fungsi. Distribusi luas flavonoid. Flavonoid adalah pigmen tumbuhan yang paling penting untuk pewarnaan bunga menghasilkan pigmentasi kuning atau merah / biru di kelopak. menelan jumlah yang signifikan dalam diet mereka. Kedua set senyawa memiliki bukti kesehatan modulasi efek pada hewan yang memakannya. Warna-warna itu adalah tujuan untuk menarik hewan penyerbuk. juga yang dikenal sebagai vitamin P dan Citrin [1]. semanggi.2-benzopyrone) struktur.

yang ditemukan dalam kacang-kacangan. transportasi menghambat cAMP-merangsang sekresi Cl-dalam usus [13] [sunting] agen menstabilkan kapiler Bioflavonoid seperti rutin. flavonoid sendiri yang sedikit atau tidak ada nilai antioksidan langsung [9] [10]. tetapi yang paling mungkin adalah karena tingkat asam urat meningkat yang dihasilkan dari metabolisme flavonoid [11] Menurut Frei. penelitian yang dilakukan di Linus Pauling Institute dan dievaluasi oleh Otoritas Keamanan Makanan Eropa menunjukkan bahwa. dengan sebagian besar dari apa yang diserap dengan cepat dimetabolisme dan dikeluarkan. setelah asupan makanan.[edit] Antioxidant activity Flavonoid (baik flavonol dan flavanol) yang paling sering dikenal karena aktivitas antioksidan secara in vitro. terutama peran putatif mereka dalam pencegahan kanker dan penyakit kardiovaskular. dan karena itu mungkin nilai dalam pencegahan kanker.. Seperti kondisi tubuh tidak seperti kondisi tabung reaksi terkontrol . bawang dan apel [12] Penelitian mereka juga menunjukkan bahwa hanya sejumlah kecil flavonoid yang diperlukan untuk melihat manfaat medis. Dr Zuo-Feng Zhang. 144 . "Kami sekarang dapat mengikuti aktivitas flavonoid dalam tubuh. Peningkatan kapasitas antioksidan darah terlihat setelah konsumsi makanan kaya flavonoid tidak disebabkan langsung oleh flavonoid sendiri. [11] [edit] Diarrhea Sebuah studi yang dilakukan di Rumah Sakit Anak & Research Center Oakland. dan teh atau bahkan anggur merah telah dikaitkan dengan senyawa flavonoid daripada nutrisi yang dikenal dan vitamin. ditemukan di stroberi dan teh hijau dan hitam. bekerja sama dengan para ilmuwan di Heinrich Heine University di Jerman. " [edit] Other health benefits [edit] Cancer Proses bersiap-siap untuk menyingkirkan senyawa yang tidak diinginkan menyebabkan apa yang disebut enzim fase II yang juga membantu untuk menghilangkan mutagen dan karsinogen. Konsumen dan produsen makanan telah menjadi tertarik pada flavonoid untuk properti yang mungkin mereka obat. efek menguntungkan dari buah. ditemukan di brussel sprouts dan apel . quercetin dan luteolin dapat menghambat perkembangan cairan yang mengakibatkan diare dengan menargetkan fibrosis Cl transmembran konduktansi usus kistik regulator -.. telah menunjukkan bahwa epikatekin. diosmin. UCLA Jonsson Cancer Center dan profesor kesehatan masyarakat dan epidemiologi di UCLA School of Public Health mengatakan flavonoid yang tampaknya menjadi catechin termasuk paling protektif. troxerutin dan hidrosmin memiliki norma vasoprotective. flavonoid dan polifenol lainnya yang kurang diserap (kurang dari 5%). sayuran. dari. dan quercetin. Meskipun bukti fisiologis belum dibentuk. kaempferol. monoxerutin. Flavonoid dapat menginduksi mekanisme yang membantu membunuh sel kanker dan menghambat invasi tumor "[11] UCLA kanker peneliti telah menemukan bahwa peserta studi yang makan makanan yang mengandung flavonoid tertentu tampaknya dilindungi dari mengembangkan kanker paru-paru. dan satu hal yang jelas adalah bahwa tubuh melihat mereka sebagai senyawa asing dan sedang berusaha untuk menyingkirkan mereka. [8] Atau. Mengambil suplemen makanan besar tidak memberikan manfaat ekstra dan dapat menimbulkan beberapa risiko.

and remove this template when finished. untuk lebih spesifik. Please update this article to reflect recent events or newly available information. [14] [15] namun dalam tes yang diuraikan di atas sekarang muncul efek antioksidan bermanfaat minimal sebagai antioksidan dengan cepat dikeluarkan dari tubuh. Please see the talk page for more information. [edit] Epicatechin Epicatechin (EC) Epikatekin meningkatkan aliran darah dan dengan demikian tampaknya baik untuk kesehatan jantung. teh (teh terutama putih dan hijau). Please update this article to reflect recent events or newly available information.[edit] Important flavonoids This article may need to be updated. merah anggur. dan cokelat gelap (dengan kandungan kakao dari tujuh puluh persen atau lebih besar). bawang [16] [17]. bahan utama coklat hitam. Hal ini juga dapat membantu untuk mencegah beberapa jenis kanker. Kakao. sebuah flavonol. (bawang merah terutama [19]) pulsa [20]. ginkgo biloba. seperti rutin dan quercitrin. (October 2009) [edit] Quercetin Main article: quercetin Quercetin Quercetin adalah flavonoid dan. ditemukan dalam jeruk. soba buah dan bawang. Ini adalah bentuk aglikon dari sejumlah glikosida flavonoid lainnya. [edit] Important dietary sources This article may need to be updated. peterseli [18]. Quercetin membentuk quercitrin glikosida dan rutin bersama dengan rhamnosa dan rutinose. berisi jumlah yang relatif tinggi epikatekin dan telah ditemukan memiliki hampir dua kali kandungan antioksidan dari anggur merah dan sampai tiga kali lipat dari teh hijau dalam in-vitro tes. seabuckthorn. masing-masing. 145 . and remove this template when finished. Please see the talk page for more information. (October 2009) Sumber yang baik dari flavonoid termasuk buah jeruk semua. namun saat ini ada penelitian lebih dibutuhkan di daerah ini. berry.

[edit] Citrus

Berbagai flavonoid yang ditemukan dalam buah jeruk, termasuk jeruk. Bioflavonoid jeruk hesperidin meliputi (a glikosida dari hesperetin flavanon), quercitrin, rutin (dua glikosida flavonol dari quercetin), dan tangeritin flavon. Selain memiliki aktivitas antioksidan dan kemampuan untuk meningkatkan tingkat intraseluler vitamin C, rutin dan hesperidin memberi efek menguntungkan pada permeabilitas kapiler dan aliran darah. Mereka juga menunjukkan beberapa manfaat anti alergi dan anti-inflamasi dari quercetin. Quercetin juga dapat menghambat reverse transcriptase, bagian dari proses replikasi retrovirus [21] Relevansi terapi inhibisi ini belum ditetapkan.. Hydroxyethylrutosides (DIA) telah digunakan dalam pengobatan permeabilitas kapiler, mudah memar, wasir, dan varises

[edit] Tea
This section does not cite any references or sources.
Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (October 2009)

Bai Hao Yinzhen from Fuding in Fujian Province, widely considered[citation needed] the best grade of white tea Flavonoid teh hijau adalah senyawa antioksidan kuat, pikir untuk mengurangi kejadian kanker dan penyakit jantung. Flavonoid utama dalam teh hijau adalah kaempferol dan catechin (katekin, epikatekin, epikatekin galat (ECG), dan epigallocatechin gallate (EGCG)). Dalam memproduksi teh seperti teh oolong dan teh hitam, daun yang diizinkan untuk mengoksidasi, di mana enzim hadir dalam teh mengubah beberapa atau semua katekin untuk molekul yang lebih besar [kutipan diperlukan]. Namun, teh hijau diproduksi dengan dikukus daun segar-potong, yang inactivates enzim, dan oksidasi tidak signifikan terjadi. Teh putih adalah yang paling diproses dari 146

teh dan ditampilkan [kutipan diperlukan] untuk menyajikan jumlah tertinggi katekin diketahui terjadi di sinensis kamelia.

[edit] Wine
See also: Phenolic compounds in wine ulit anggur mengandung sejumlah besar flavonoid serta polifenol lainnya [22]. Kedua merah dan anggur putih mengandung flavonoid, namun sejak anggur merah diproduksi oleh fermentasi dalam kehadiran kulit anggur, anggur merah telah diamati mengandung kadar flavonoid, dan polyphenolic lain seperti resveratrol

[edit] Dark chocolate
Flavonoid ada secara alami dalam kakao, tetapi karena mereka dapat menjadi pahit, mereka sering dihapus dari coklat, bahkan berbagai gelap [23]. Sementara flavonoid yang hadir dalam coklat susu, penelitian telah menunjukkan bahwa mereka tidak mudah diambil oleh tubuh;. mereka juga tidak mudah diambil ketika coklat gelap dikonsumsi bersama susu [24]

[edit] Subgroups
Lebih dari 5000 flavonoid alami telah ditandai dari berbagai tanaman. Mereka telah diklasifikasikan menurut struktur kimianya, dan biasanya dibagi lagi menjadi sub kelompok berikut (untuk lebih lanjut membaca lihat [25]):

[edit] Flavones
Flavones are divided into four groups:[26] Skeleton Functional groups Description 32,3hydroxy dihydro l Structural formula

Group

Examples

147

Flavone

2phenylchromen -4-one

Luteolin, Apigenin, Tangeritin

Flavonol 3-hydroxy-2or phenylchromen 3-4-one hydroxyflavone

Quercetin, Kaempferol, Myricetin, Fisetin, Isorhamnetin, Pachypodol, Rhamnazin

Flavanone

2,3-dihydro-2phenylchromen -4-one

Hesperetin, Naringenin, Eriodictyol, Homoeriodictyol

Flavanonol or 33-hydroxy-2,3Hydroxyflavano dihydro-2ne phenylchromen or -4-one 2,3dihydroflavonol

Taxifolin (or Dihydroquercetin), Dihydrokaempfero l

[edit] Isoflavones
Isoflavon menggunakan kerangka 3-phenylchromen-4-satu (tanpa substitusi gugus hidroksil pada karbon pada posisi 2). Contoh: genistein, daidzein, Glycitein

148

Epigallocatechin (EGC). or polymers of the flavanols.4-diol (leucoanthocyanidin) • Flavan-3-ols (also known as flavanols) and Proanthocyanidins Flavan-3-ols use the 2-phenyl-3. oligomers. and proanthocyanidins Flavan structure Derivatives of flavan.4-diols.4-dihydro-2H-chromen-3-ol skeleton. Gallocatechin (GC). Epigallocatechin 3-gallate (EGCg)) Proanthocyanidins are dimers. Gallocatechin 3gallate (GCg)).[edit] Flavan-3-ols. Epicatechins (Epicatechin (EC). Flavan-3. Catechin 3-gallate (Cg). [edit] Anthocyanidins 149 . Skeleton Name Flavan-3-ol Flavan-4-ol Flavan-3. Epicatechin 3gallate (ECg). trimers. Catechins (Catechin (C). Flavan-4-ols.

Malvidin. delphinidin. Petunidin [edit] Availability through microorganisms Beberapa artikel penelitian terbaru menunjukkan produksi efisien molekul flavonoid dari rekayasa genetik mikroorganisme [27] [28] [29] MODUL XV XV.Flavylium skeleton of anthocyanidins • • Anthocyanidins Anthocyanidins adalah aglycones dari anthocyanin. pelargonidin. Asam nukleat terdiri dari dua macam cincin lingkar yang berbeda yaitu pirimidina dan purin. SENYAWA HETEROSIKLIK DAN ASAM NUKLEAT Senyawa heterosiklik dari senyawa pyrimidin dan purin Senyawa heterosiklik adalah senyawa organik berbentuk lingar yang tersusun dari 2 atom atau lebih. Salah satu dari senyawa heterosiklik itu adalah asam nukleat. Primidina adalah senyawwa lingkar cincin enam yang dua dari anggota cincinnya adalah atom nitrogen selebihnya adalah atom karbon yang mempunyai struktur seperti berikut : N N H pirimidin Dan senyawa purin terdiri penggabungan dua senyawa lingkar yang terdiri dari cincin lima dan enam yang empat dari anggota cincinnya adalah atom nitrogen selebihnya atom karbon dengan struktur sebagai berikut : N N 150 . Anthocyanidins menggunakan flavylium (2-phenylchromenylium) ion kerangka Contoh: cyanidin. peonidin.

uracil. Secara garis besarnya asam nukleat terdiri dari asam ribosa nukleat (RNA) dan asam deoksi ribosa nukleat.N purin N H Atom Hidrogen H merupakan pusat reaksi dari baik basa purin maupun basa pirimidin Asam nukleat dan nukleotida. Asam nukleat terdiri dari tiga kompenen yakni gugus basa nukleat ( adenin. dan setiap nukleosida dapat dipecah oleh enzim katalis hidrolisa menjadi senyawa pentosa sederhana dan senyawa heterosiklik purin dan pirimidin Asam nukleat Posfat gula Nukleotida H2O Enzim Basa nukleat H3PO4 + gula Nukleosida Basa amina H3O+ Gula + amina heterosiklik 151 . menegndalikan pertumbuhan suatu sel dan pembelahan sel. Selanjutnya setiap nukleotida dapat dipecah oleh enzim katalis hidrolisa menghasilkan nukleosida dan asam posfat H3PO4. kedua asam nukleat ini berfungsi memberikan informasi genetik kepada sel makhluk hidup. enzim katalis hidrolisa yang memecah asam nukleat menjadi gugus-gugus penyusunnyya yang disebut nulkeotida. gugus karbohidrat (ribosa dan deoksi ribosa). di. Penandaan DNA pada suatu sel ditentukan oleh semua informasi dari sel induk. guanin cytosin.. dan protein-protein lainnya yang diperlukan untuk semua peran sel. tri dan seterusnya). dan gugus posfat ( mono. serta perintah biosintesa dari enzim. thymin). Seperti protein asam nukleat adalah polimer.

Nama deoksi berasal dari atom oksigen pada posisi 2’ hilang dari molekul ribose. tanda ‘ pada angka 2 menunjukan posisi atom oksigen dalam molekul gula nukleotida. CH2OH H H OH Ribosa OH H OH CH2OH H OH H OH H 2’ deoksiribosa Ada dua macam senyawa purin yang taerdapat pada asam nukleat yakni Adenin dan guanine dengan struktur sebagai berikut : NH2 O N N N N NH2 N Adenin N H Guanin N N H Ada 3 macam senyawa pirimidin yang terdapat pada asam nukleat yakni : NH2 N O H3C N N O 152 .Komponen gula dalam asam ribosa nukleat adalah ribose dan komponen gula dalam deoksiribosa nukleat adalah 2’-deoksiribosa. Dan nama tanpa tanda ‘ menunjukkan posisi atom oksigen pada basa amina cincin heterosiklik.

N H Cytosin O N H Uracil O N H Thymin O Struktur DNA NH2 O N N N N NH2 N H2PO3CH2 H OH Ribosa OH H N H2PO3CH2 H OH 2’ deoksiribos H H N N NH2 H3C N H CH2OH H H OH Ribosa OH H H OH H N O CH2OH O N N H O 2’ deoksiribosa 153 .

NH2 O N N N N NH2 N Adenin CH2OH H H OH Ribosa NH2 N O H3C N N OH H H OH H 2’ deoksiibosa O H OH CH2OH N H Guanin OH N N H N H Cytosin O N H Uracil O N H Thymin O CH2OH OH CH2OH 154 CH2OH .

H H OH Ribosa Sintesa DNA XVI. poliepoksi. pati yang terdiri dari unit monomer heksosa. dan lain-lain. Contoh reaksi polimerisasi addisi adalah sebagai berikut : O O O 2 C6H5-C-Oo = Ino In-H2C=CH2o C6H5-C--O-O--C-C6H5 Ino + H2C=CH2 Klassifikasi polimer Polimer Sintetik dapat digolongkan berdasarkan metode sintesa atau pun bisa juga tahap pembentukan rantai polimer atau tahap pembentukan polimer. polistirena. polyester. Polimer alami adalah protein yang terdiri dari unit monomer asam-asam amino. Banyaknya pengulangan pada molekul monomer menunjukkan derajad polimerisasi dari molekul polimer tersebut. polipropilena. Makin banyak unit monomer pada suatu molekul polimer maka sifat kimianya makin inert. nilon. dan fosfat. Tahap pembentukan rantai polimer disebut polimer addisi dengan istilah lain dihasilkan dengan polimerisasi reaksi berantai yang inisiatornya teraddisi ke ikatan ganda karbon-karbon untuk menghasilkan senyawa intermediet yang reakstif. Polimer bisa terbentuk melalui proses reaksi addisi dan melalui reaksi kondensasi. Polimer terbentuk dari banyyaknya monomer yang teraddisi ke ujung rantai yang reaktif dari rantai yang terbentuk. resin urea formal dehid. serat akrilat. Kategori ini mencakup banayak hal dan memerlukan kegunaan yang berbeda. Polimer sintetik adalah polimer yang dibuat dibuat dalam proses industri kimia. Berdasarkan proses pembentukanknya secara garis besar polimer dibagi menjadi polimer alami dan polimer sintetik. resin fwenolat. seperti polietilena. POLIMER OH H H OH H 2’ deoksiribosa OH Polimer adalah senyawa organic bermolekul besar yang teridiri dari unit molekul monomer yang berulang. asam nukleat yang terdiri dari unit monomer basa nukleat. polivinilklorida. ribose. Inisiator bisa bermula baik anion. 155 .

Salah satu dari radikal ini teraddisi ke molekul etilena membentuk rantai karbon radikal baru. polimerisasi berlangsung terus menerus. 156 . dan sertiap ikatan dalam polimer terbentuk secara bebas dari yang lainnnya. Inisiasi bermula ketika terbentuk sejumlah radikal yang dibentuk oleh katalis. atau radikal. tahap propagasi. Reaksi terjadi pada antara dua gugus fungsi molekul. Produksi tahunan untuk polimer ini dengan volume produksi hampir 12 juta ton. Dengan tahap pertumbuhan sebagai berikut : H2N-(CH2)6-NH2 + HOOC-(CH2)6-COOH -NH-(CH2)6-NH-CO-(CH2)6-CO. dan polimer yang dihasilkan dengan cara begini hanya mempunyai atom-atom karbon pada rantai utama.+ H2O Nilon 66 Reaksi polimerisasi radikal. Nilon adalah merupakan suatu polimer poliamida yang terbentuk dari reaksi asam dikarboksilat dan senyawa diamina. Dengan katalis radikal benzoil peroksida. dan tahap terminasi. Polimer biasanya dihasilkan dari dua monomer yang salling berikatan dan biasanya mempynyai atom lainnya yang teraddisi ke atom karbon pada rantai utama. jumlah unit monomer bisa dari beberapa ratus sampai beberapa ribu unit rantai monomer. Semua reaksi radikal berantai berlangsung dalam tiga macam tahap reaksi yakni tahap inisiasi.kation. kationik dan anionic Beberapa polimer alkena berberat molekul rendah mengalami reaksi polimerisasi yang cepat ketika berkontak dengan sejumlah inisiator radikal. Polietilen adalah salah satu molekul polimer berantai pertama yang dibuat diindustri secara komersil yang sederhana yang telah diproduksi semenjak tahun 1943. Reaksi polimerisasi propilena biasanya berlangsung pada tekanan 1000 – 3000 atm dan suhu tinggi 100 – 250 oC. Polietilen dihasilkan dengan reaksi inisiasi polimerisasi etilen dengan tahap pembentukan polimer sebagai berikut : Ino + H2C=CH2 In-H2C-CH2o + H2C=CH2 In-H2C-CH2-H2C-CH2-H2C- In-H2C-CH2-H2C-CH2o + H2C=CH2 CH2o + H2C=CH2 In-H2C-CH2-H2C-CH2-H2C-CH2-H2C-CH2o Polietilen Tahap pembentukan polimer yang disebut dengan pertumbuhan polimer kondensasi yang terbentuk dengan proses polimerisasi dimana tahap pembentukan ikatan terjadi pada reaksi polar.

(HC-CH2-)nHC-CH2o + In-(HC-CH2-)m-HC-CH2o 157 .Ino + H2C=CH2 In-H2C-CH2o + H2C=CH2 In-H2C-CH2-H2C-CH2-H2C- In-H2C-CH2-H2C-CH2o + H2C=CH2 CH2o + H2C=CH2 In-H2C-CH2-H2C-CH2-H2C-CH2-H2C-CH2o Polietilen Reaksi polimerisasi polipropilena terjadi dalam lima tahap berikut : Tahap 1 ( inisiasi ) O O O 2 C6H5-C-Oo = Ino In-HC-CH2o H3C Tahap 3 ( propagasi ) In-HC-CH2o + H3C-HC=CH2 H3C In.(HC-CH2-)nHC-CH2o + In-(HC-CH2-)n-HC-CH2o H3C H3C H3C H3C In-H2C-CH2-HC-CH2-CH2-CH-n(CH2-HC-)-In H3C H3C H3C H3C Tahap 5 ( terminasi ) In.-H2C-CH2-HC-CH2o + n H3C-H2C=CH2 H3C H3C In-HC-CH2-CH-CH2o H3C H3C In-(HC-CH2-)n-HC-CH2o H3C H3C C6H5-C--O-O--C-C6H5 Tahap 2 Ino + H3C-HC=CH2 Tahap 4 (Quenching) In.

Reaksi polimerisasi kationik terjadi dengan jalur reaksi berantai dan memmerlukan proton yang kuat atau asam Lewis sebagai inisiator. dan juga dengan mekanisme reaksi radikal.H+ (-CH-CH2-)n S 158 . Reaksi berantai ini terjadi melalui reaksi addisi elektrofilik dari karbokation intermediet ke ikatan ganda karbon-karbon dari unit monomer lainnya Tahap 1 (inisiasi) H+ + S-HC=CH2 Tahap 2 ( propagasi ) + HC-CH3 S + HC-CH3 + SHC=CH2 S H3C-CH-CH2-CH+ S S H3C-CH-H2C-CH+ + n S-H2C=CH2 S Tahap 4 (Quenching) (H3C-CH+-)n + OH. S S (H3C-CH-)n-H2C-CH+ S S (-CH2-CH-)n + H2O S Tahap 5 ( terminasi ) I (-+CH-CH3)nS .H3C H3C H3C H3C -(H2C-CH2-)n-HC-CH2-CH2-CH-n(CH2-HC-)mH3C H3C H3C H3C Reaksi polimerisasi kationik Senyawa turunan monomer alkena tertentu dapat dipolimerisasi dengan mekanisme reaksi polimerisasi kationik.

(-CH2-CH-)nS Tahap 1 (inisiasi) Nu:. Contohnya H2C=CH + Nu:S . S = substituen gugus penarik electron Reaksi polimerisasi anionic Monomer alkena yang mengandung substituen gugus penarik electron dapat dipoolimerisasi dengan katalis anionic.+ S-HC=CH2 - Nu-CH2-CH:. Reaksi berantai dapat terjadi dimana tahap yang paling menentukan reaksi adalah tahap addisi nukleofil dari anion ke monomer tak jenuh.+ H2C=CH S S Nu-CH2CH-H2C-CH:S S :HC-CH2-Nu S Tahap 2 ( propagasi ) - :HC-CH2 -Nu + SHC=CH2 S -:HC-CH2-CH2-CH-Nu S S - :HC-CH2-HC-CH2-Nu + n S-H2C=CH2 S S -:(-HC-CH2-)n-HC-CH2-Nu S S Tahap 4 (Quenching) 159 .-(H2C-CH2-)n-HC-CH2-CH2-CH-n(CH2-HC-)H3C H3C H3C H3C Dimana Nu = inisiator nukleofilik.

CN H2C=C-COOCH3 α siano akrilat + -OH CN HO-CH2-C:COOCH3 CN -CH2-C COOCH3 Super glue n Stereokimia dari polimer Secara garis besarnta polimer mempunyai tiga bentuk stereokimia 160 .(-CH-CH2-)n .Nu:S (-CH-CH2-)n S Monomer akrinlonitril (H2C=CHCN). methyl methakrilat (H2C=C(CH3)COOCH3. Kulit adalah sumber yang terbaik dari inisiator dasar yang diperlukan. Karena ikatan ganda karbon mempunyai dua gugus penarik electron. Salah satu contoh yang paling menarik dari reaksi polimerisasi anionic adalah super glue satu tetesnya mempunyai daya rekat 2000 lb. Tahap 5 ( terminasi ) Nu:. dan stirena (H2C=CHC6H5) semuanya dapat mengalami reaksi polimerisasi anionic. Dengan adanya sediit air atau basa pada permukaan bahan sudah cukup untuk memulai reaksi polimerisasi sianokrilat dan selanjutnya terjadi penggabungan antar molekul monomer. Super glue adalah salah satu contoh produk yangpaling sederhana dari rekasi polimerisasi anionic dari bahan murni metal a-sianokrilat. meskipun diperlukan radikal sebagai inisiator polimerisasi untuk produksi skala komersil. dan banyak orang menemukan jarinya lengket setelah menyentuh super glue. sehingga reaksi addisi anionic dapat berlangsung dengan mudah dan cepat.- :(HC-CH2-)n + H+ S (-CH2-CH-)n + H2O S .

maka masing-masing molekul dapat bergeser satu sama lainnya bila dipanaskan. telefon. Elastomer 161 .Isotactic H3C H H3C H H3C H H3C H H3C H Syndiotactic H3C H H H3C H3C H H H3C H3C Atactic H3C H CH3 H H3C H H CH3 H H3C Polimerisasi diena ( karet alam dan karet sintetis ) kopolimer Polimer nilon Polimer poli uretahn hubungna Struktur dan kimia polimer hubungan Struktur dan sifat fisika polimer Klassifikasi polimer sinthetik berdasarkan sifat fisikanya yang dapat digunakan untuk menetukan hubungan sifat fisika dengan struktur polimer. b. sedangkan yang lainnya seperti nilon dan poli etilen adalah kristal. thermoplastic. Pengaliran menyebabkan polimer ini mempunyai oreantasi bentuk kristal sepanjang gulunngan fiber. Pada dasarnya penggolongan polimer berdasarkan sifat fisikanya dapat digolongkan menjadi empat golongan bedar yakni a. Thermoplastik ini bisa dibuat menjadi mainan anak-anak. Karena thermopalstik tidak mempunyai ikatan silang. atau beribu-ribu jenis produk lainnya. proses ini mengakibatkan penguatan batas kekuatan tarik polimer. kemudian serat didinginkan dan dipintal. c. dan poli etilen. Polimer ini keras pada suhu kamar dan lunak dan meleleh bila dipanaskan. Fiber. Beberapa produk polimer thermoplastic seperti polimetilmetakrilat. Menurut kebanyakan orang mengira polimer adalah thermoplastic sebagai plastic. Fiber adalah serat tipis yang dihasilkan dari ekstruding dan pelelehan polimer melalui lobang yang halus pada pemintalan serat. dacron. Beberapa jenis produk polimer yang tergolong semi kristal adalah nilon. yang digunakan sebagai pleksi glass adalah amorf. alat tidur.

Bila ditarik rantai lurus yang tersusun secara random akan menjadi melar sesuai dengan arah tarikan Gaya Van der Waals yang bekerja terlalu lemah dan sedikit sekali terjadi yang bisa mempertahankan oreantasi ini. Balelit adalah salah satu contoh resin thermosetting yang pertama kali diproduksi tahun 1907 oleh Leo Baekeland. yang telah banyak diperdagangkan dalam waktu yang lama dari pada polimer sintetik lainnya. Karet alam mempunyai rantai yang panjang dan terjadi ikatan silang secara elektrostatik. Sebaliknya Getta percha adalah polimer kristalin yang tinggi bukan elastomer.Elastomer adalah polimet yang bersifat amorf mempunyai kemampuan memanjang dan mengkerut menjadi bentuk awalnya kembali. berupa massa yang tak larut bila dipanaskan. dan polimer berubah menjadi bentuk yang paling stabil yakni berupa massa seperti bebatuan. Bakelit adalah molekul yang sangat besar sekali. Resin thermosetting. dan bahkan dipakai untuk keperluan suhu tinggi seperti ujung peluru kendali. terbentuklah beberapa ikatan silang. Bakelit banyak sekali digunakan dalam bentuk cairan kental untuk perekat. pelapis. Ranntai molekulnya tak beraturan untuk mencegah pembentukan kristal yang kaku. akan tetapi dengan geometri tak beraturan sulit untuk terjadinya bentuk kristal. Ikatan silang pada bakelit dan bahan thermosetting lainnya adalah bentuk tiga dimensi dan sangan rumit. Karet alam adalah salah satu contoh elastomer. Polimer-polimer ini dapat membentuk ikatan silang untuk mencegah pergeseran antar molekul antara stu sama lainnya. OH H+ + H-C=O H Fenol formal dehid HO OH OH OH OH OH Resin fenol formal dehid ( bakelit ) 162 . sehingga tidak bisa digambarkan bentuk rantai polimernya. Pada saat pemanasan molekul air dibebaskan. Secara kimia bakelit adalah resin fenolik yang dihasilkan dari reaksi fenol dan formal dehid. d. Resin thermosetting adalah polimer yang banyak berikatan silang dan memadat sampai menjadi keras. akan tetapi dengan adanya elastomer akan sulit membentuk kumparan yang tersusun secara random bila dilakukan penarikan.

“ Organic chemistry “ 3rd ed Prentice Hall Publ. Boyd. Brown “Organic Cemistry” 1975.886) 5. Freeman and Company. A.Daftar pustaka : 1.T. 7. “ Organic Chemistry” Schaum’s outlineseries 1977. L. Ltd 1957 3. "http://en. F. Fhiser “ Organic Chemistry “ Mazen Co. Morrison and N. H.wikibooks. Murry “ Organic chemistry “ Brooks/cole Publ. F. John Mc. Wadworth Publ. T. 4. 1984. R. 1978.org/wiki/Organic_Chemistry/Overview_of_Functional_Groups" 163 . Co. R. Meislich et al. (pp 1 – 995) 6. Co. Geissman “ Principles of organic chemistry” 3rd ed 1968 W. 2.H. (pp 1 . Co.

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