2012 FKIP UNIB

Metana

Kekule
Cair

C2H6O

Gas

Agust Kekul melalui menerangkan fakta tersebut dengan menggunakan suatu model atom. Model atom untuk penyusun diusulkan sebagai berikut:

Atom Hidrogen Oksigen

Model atom H O

Karbon

Keterangan : Garis dalam hal ini disebut garis valensi

Isomer
H H H H C H H C O H H H C O C H H H

H3C O CH3

H3C

C OH H2

Kekul

H 4H

C H

Lewis
Teori ini mengembangkan konsep yang dikemukakan oleh Bhor. Bhor berpendapat bahwa atom terdiri dari inti atom dan elektron, elektron mengelilingi inti sesuai dengan kulitnya.
Atom C dengan no atom 6 Atom Ne dengan no atom 10

kulit 1 = 2 e kulit 2 = 4 e (belum penuh)

kulit 1 = 2 e kulit 2 = 8 e (penuh)

Konsep Bulir
Luwis mengusulkan konsep yang disebut bulir. 6 C, 2 elektron di kulit K dan 4 elektron di kulit L, C dinotasikan oleh Lewis mempunyai 4 titik.
C

Menurut Kekul C mempunyai garis valensi 4 buah dan menurut Bhor atom karbon mempunyai elektron valensi 4 buah
H C

4 H

C H H H

Linus Pauling
memanfaatkan persamaan gelombang Erwin Schrodinger. Elektron mempunyai sifat dualistik yaitu sebagai partikel dan sebagai gelombang.

_ ( 8

2 ) (
2

H X

) = E

= ( E _ Ep)

Penyelesaian dari persamaan di atas akan diperoleh harga-harga E dan dari akan diperoleh 2 adalah orbital. Orbital didifinisikan sebagai daerah disekitar inti yang keboleh jadiannya menemukan elektron paling besar.
2

Harga-harga E dan

Harga E bergantung pada harga-harga n dan l, n adalah bilangan kuantum utama, n = 1, 2, 3, . dst, l adalah bilangan kuantum azimut l = 0, 1, 2, 3, (n-1) Untuk n = 1, maka l = 0. Jadi untuk n = 1 diperoleh 1 tingkat energi dengan harga yaitu n = 1 dan l = 0 . Untuk n = 2, maka l = 0 dan l = 1. Jadi untuk n = 2 diperoleh 2 tingkat energi dengan harga yaitu n = 2 dan l = 0, serta n = 2 dan l = 1.

Bentuk diagram energinya sbb :

n=3

E
n=2

n=1

Orbital
Harga
2

bergantung pada n, l dan m, n = 1, 2, 3, . dst,

n bilangan kuantum utama

l bilangan kuantum azimut

l = 0, 1, 2, 3, (n-1)

m bilangan kuantum magnetik m = -l, 0, + l Untuk n = 1 maka l = 0 dan m = 0 Jadi untuk n =1 akan terdapat satu orbital dengan harga l = 0 dan m = 0 yang orbitalnya disebut orbital 1s. y
x z

orbital 1 s

Untuk n = 2, diperoleh dua harga l yaitu l = 0 dan l = 1. Jadi :

n = 2, harga l = 0 dan m = 0 terdapat satu orbital adalah orbital 2s. n = 2 harga l = 1 dan harga m = -1, m = 0 dan m = +1. terdapat tiga orbital adalah orbital 2p. Untuk : n = 2, l = 1, dan m = -1 orbitalnya 2px, n = 2, l = 1, dan m = 0 orbitalnya 2py n = 2, l = 1, dan m = +1 orbitalnya 2pz

Gambar masing-masing orbital 2 s dn 2p adalah sbb :

y x z y x z y x z

orbital 2 px

orbital 2 py

orbital 2 pz

Pengisian Orbital
2p

n=2

2s

Ada 3 aturan

n=1

1s

1. Aufbau : pengisian dalam orbital ikatan dimulai dari orbital yang mepunyai energi terendah kemudian dilanjutkan pada orbital yang mempunyai energi lebih tinggi. 2. Hund : pengisian berpasangan dalam orbital ikatan tidak akan terjadi sebelum orbital yang mempunyai E sama terisi 1 . 3. Pauli : pengisiaan dalam orbital ikatan hanya bisa terjadi bila mempunyai spin yang berlawanan.

Orbital Atom C

2p

n=2

E
n=1

2s

y x
1s

orbital 2s, 2 px, 2py, 2pz suatu atom C

Hibridisasi sp3
CH4 : atom C membentuk 4 ikatan kovalen dengan 4 atom H, keempat ikatan kovalen, panjang ikatan (C-H =1,09 A) dan energi disosiasi sama (104 kkal/mol).

2p

2p

E
2s

E
2s

E
2s 2p

grand state

exaited state: 1 dipromosikan ke orbital kosong

1 orbital 2s dan 3 orbital 2p bergabung membentuk hibridisasi sp3

109,5

bentuk orbital atom C sp3

bentuk orbital atom H (orbital 1 s)

H
109,5 109,5

(sp3 - 1s) H C H

Hibridisasi sp2
Di dalam senyawa etena [ C2H4 atau H2C = CH2] terdapat 1 ikatan rangkap

2p

2p

2p

E
2s

E
2s

E
2s 2p

grand state

exaited state: 1 dipromosikan ke orbital kosong

1 orbital 2s dan 2 orbital 2p bergabung membentuk hibridisasi sp2

120

120

orbital C

sp2

orbital C sp2 dan orbital 2p yang tidak terhibridisasi

H (sp2-sp2)
120 120

H C C (2p-2p)

H (sp2-1s)

masing-masing orbital 2p saling overlap antar sisi membentuk ikatan pi

Hibridisasi sp
Di dalam C2H2 terdapat 1 ikatan rangkap tiga dan 2 ikatan tunggal.

2p

2p

2p

E
2s

E
2s

E
2s 2p

grand state

exaited state: 1 dipromosikan ke orbital kosong

1 orbital 2s dan 1 orbital 2p bergabung membentuk hibridisasi sp

Orbital atom C sp ini akan terjadi apabila atom karbon dalam molekul terikat oleh ikatan rangkap tiga. Bentuk orbital C sp adalah linier, gambar orbitalnya sbb:

180

orbital C sp orbital C sp dan 2 orbital 2p yang tidak terhibridisasi

Dalam molekul C2H2 , 2 orbital sp pada atom C (1 dan 2) masingmasing akan overlap dengan 1 orbital 1s dari atom H dan 1 orbital sp dari atom C yang lain. Overlaping dari masing-masing orbital adalah sebagai berikut

(sp-sp) C C 2 (2p-2p)

(sp-1s) H

masing-masing orbital 2p saling overlap antar sisi membentuk ikatan pi

Dua orbital 2p yang lain yatiu orbital yang tidak terhibridisasi dari masing-masing atom C (1 dan 2) dapat saling overlaping membentuk 2 ikatan phi. Ketiga teori struktur dari Kekul, Lewis dan Linus Pauling sering dikenal dengan teori Ikatan Valensi

Struktur termampatkan
H H C H C C H CH3-C CH

H H C H

H C H O H CH3-CH2-OH atau CH3CH2OH

Ikatan yang biasa tidak ditulis adalah ikatan tunggal Seorang Chemist menulis struktur senyawa organik dengan struktur termampatkan akan tetapi di dalam pemikirannya harus sudah tergambar bahwa struktur yang ditulis tersebut adalah struktur Luwis dan Pauling.

Organic compound

contain not only C-C bonds but also C-H bonds. C-C and C-H bonds tend to be nonpolar because there is a small difference in electronegativites Most (but not all) organic compounds are relatively non-polar
generally not very soluble in water

Classes of organic compound

Organic Compounds

Hydrocarbons

Functional Groups

The simplest organic compounds are the hydrocarbons:

organic compounds that contain only carbon and hydrogen four general types:
alkanes alkenes alkynes aromatic hydrocarbons

Hydrocarbons
H H

H H H

H Aliphatic Aromatic

Alkanes

Alkenes

Alkynes

CycloAlkanes

Alkanes

Only carbon and hydrogen All single bonds

H H

C H

C
H

Alkenes

Only carbon and hydrogen A carbon to carbon double bond

H
C H C

H H

(Double bond: 4 electrons)

Alkynes

Only carbon and hydrogen A carbon to carbon triple bond

H C

C H

(Triple bond: 6 electrons)

31

Cycloalkanes
Cycloalkanes are represented by polygons. A triangle represents cyclopropane, a square represents cyclobutane, a pentagon represents cyclopentane, and so on.

Aromatic compounds and benzene

Aromatic compounds contain benzene. Benzene, C6H6 , is represented as a six carbon ring with 3 double bonds. Two possible resonance structures can be drawn to show benzene in this form.
H H H H H H H H H H H

Functional Groups
Most organic chemistry involves substituents, which are groups attached to hydrocarbon chains.
The substituents of organic molecules often contain O, N, S and P also are called functional groups They are the chemically functional parts of the molecules.

Organic compounds can be classified according to their functional groups. They symbol R represents any carbon chains or rings attached to the functional group.

Halogens
Single Bonds Functional Groups: Replace H in Hydrocarbons

Oxygen Containing
Double Bonds Nitrogen Containing

Sulfur Containing

Halogen
Elements in Groups VII F, Cl, Br, I

CH3 CH2 CH2 CH2

CH3 CH3 C CH3 F

R-F

R-I

CH3-Br

Ether

Has 1 oxygen
H C C O C H

No O-H or C=O group

H H H

The oxygen is sandwiched between two carbon atoms

Alcohols

Only one oxygen Has an O-H functional group Can classify as 1/2/3 according to position of O-H group on carbon skeleton

H H C H

H C H O H

Phenols

Only one oxygen

Has an O-H group

The O-H group is directly attached to a benzene ring

Aldehydes

Only one oxygen

H H C H C

Has a C=O group

C=O group is at the end of carbon chain, so is next door to a hydrogen atom

Ketones

Only one oxygen

Has a C=O group

C=O group is not at the end of carbon chain, so is next door to 2 carbons

C
H

C
H

Acetone

Carboxylic acids

Has 2 oxygens

H H C C

Has O-H and C=O groups on the same carbon atom This -COOH group has to be at the end of a carbon chain

Acetic acid

Esters

H O H

Has 2 oxygens One oxygen is part of a C=O bond, the other is next door, sandwiched between two carbons

C
O C H

H H

Methyl acetate

Functional Groups with Three Oxygens

O O
Acid Anhydride RCOCR' O O CH3COCCH3 O O C6H5COC(CH2)5CH3

Amines
In amines, the functional group is a nitrogen atom. H H C N H or C N C

Methyl amine

Dimethyl amine
46

Amides
In amides, the hydroxyl group of a carboxylic acid is replaced by a nitrogen group (-NH2).

acetamide
47

CH3CHCH3 RC

Nitrile

Thiols
Thiols are carbon compounds that contain a SH group.

are named in the IUPAC system by adding thiol to the alkane name of the longest carbon chain.
Copyright 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings

49

Thiols
Thiols often have strong odors.

are used to detect gas leaks. are found in onions, oysters, and garlic.
50

Hydrocarbons

Alkanes are often called saturated hydrocarbons they contain the largest possible number of hydrogen atoms per carbon atom.

Alkanes

Organic compounds can represented in H be H H many different ways:H C H C C C H

H H H H C C C C H H H H H

H H H HH H H H molecular formula: C H (butane) H CH C C H H H H C H C H Kekule structure: C H H C CH H

4 10

H H H H

Condensed structural formula

CH3CH2CH2CH3

Line angle drawings

Alkanes
Some of the simplest alkanes:

Condensed Formula CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3CH2CH2CH2CH3

Name methane ethane propane butane pentane

You must know these!!!

Alkanes
Some of the simplest alkanes:
Condensed Formula CH3CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
You must know these!!!

Name hexane heptane octane nonane decane

Alkanes

The previous alkanes are also called straight-chain hydrocarbons:

all of the carbon atoms are joined in a continuous chain

Alkanes containing 4 or more carbons can also form branched-chain hydrocarbons (branched hydrocarbons)
some of the carbon atoms form a branch or side-chain off of the main chain

Alkanes

An example of a straight chain hydrocarbon:

C5H12 CH3CH2CH2CH2CH3 pentane

Examples of a branched hydrocarbon:

C5H12 CH3CHCH2CH3 CH3
2-methylbutane

CH3 CH3CCH3

CH3
2,2-dimethylpropane

Alkanes

The three structures shown previously for C5H12 are structural isomers:
compounds with the same molecular formula but different bonding arrangements

Structural isomers generally have different properties:

different melting points different boiling points often different chemical reactivity

Alkanes

Organic compounds can be named either using common names or IUPAC names.
IUPAC : The international Union of pure and Applied Chemistry

You must be able to name alkanes, alkenes, alkynes, and alcohols with 10 or fewer carbons in the main chain using the IUPAC naming system.

Alkanes

Alkane Nomenclature: Find the longest continuous chain of carbon atoms and use the name of the chain for the base name of the compound: longest chain may not always be written in a straight line
1 2 4 5 6

CH3 - CH - CH3
3

CH2 - CH2 - CH2 - CH3

Base name: hexane

Alkanes

Alkane Nomenclature:
Number the carbon atoms in the longest chain beginning with the end of the chain closest to a substituent
groups attached to the main chain that have taken the place of a hydrogen atom on the main chain
A substituent

2 4 5 6

CH3 - CH - CH3
3

CH2 - CH2 - CH2 - CH3

Alkanes

Alkane Nomenclature:
Name and give the location of each substituent group
A substituent group that is formed by removing an H atom from an alkane is called an alkyl group:

Name alkyl groups by dropping the ane ending of the parent alkane and adding yl

Alkanes

Alkane Nomenclature:
Common alkyl groups (substituents):
CH3 CH3CH2 CH3CH2CH2 CH3CH2CH2CH2
1 2 4 5 6

methyl ethyl propyl butyl

CH3 - CH - CH3
3

CH2 - CH2 - CH2 - CH3

2-methylhexane

Learning Check
Bagaimana menjelaskan senyawa berikut menurut teori ikatan valensi
CH3CH2OH CH3OCH3

alcohol

amine

carboxylic acid

ester

63

Classify each of the following as: alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine or amide. 1) 2) 3) CH3CH2CH2OH alcohol CH3OCH2CH3 ether CH3CH2NH2
amine

4)

O CH3COH
carboxylic acid

5)

O CH3COCH3
ester
64

Name the following compounds:

CH3CH2CHCH3
CH2CH2Br CH2CH2CH3 CH3CHCHCH3

Cl

Write the condensed structure for the following compounds: 3, 3-dimethylpentane 3-ethyl-2-methylhexane 2-methyl-4-propyloctane

1, 2-dichloro-3-methylheptane

SUKSES