RATIFICATION PAGE

Complete report of advance basic chemistry experiment entitled

“Synthetic of Tertiary Buthyl Chloride“, by :
name : Radiatul Awalia Amir
id : 1713441007
class : ICP of Chemistry Education
group : III (Three)
after checked by ssistant and assistant coordinator, so this report was accepted.

Makassar, May 2018

Coordinator assistant Assistant

Imranah, S.Pd Rislaepi

ID.1413040013

Known by,
Lecturer of Responsibility

Hardin, S.Si., S.Pd., M.Pd

NIP. 19870807 2015 04 1 004
A. THE TITTLE OF EXPERIMENT
Synthetic of Tertiary Buthyl Chloride
B. THE OBJECTIVE OF EXPERIMENT
At the end of the experiment student are expected:
1. How to prepare and use the apparatus in manufactund of organic
compounds in liquids from using
2. The principle nucleophilic substitution reaction
3. The tripical difference between SN1 and SN2
C. LITERATURE REVIEW
Hydrocarbons are compounds that contain only carbon and hydrogen and
are divided into two main classes: aliphatic hydrocarbons and aromatic
hydrocarbons. This classification dates from the nineteenth century, when organic
chemistry was almost exclusively devoted to the study of materials from natural
sources, and terms were coined that reflected a substance’s origin. Two sources
were fats and oils, and the word aliphatic was derived from the Greek word
aleiphar (“fat”). Aromatic hydrocarbons, irrespective of their own odor, were
typically obtained by chemical treatment of pleasant-smelling plant extracts.
Aliphatic hydrocarbons include three major groups: alkanes, alkenes, and alkynes.
Alkanes are hydrocarbons in which all the bonds are single bonds, alkenes contain
a carbon–carbon double bond, and alkynes contain a carbon–carbon triple bond.
Examples of the three classes of aliphatic hydrocarbons are the two-carbon
compounds ethane, ethylene, and acetylene (Brown, 2012: 53-54).
Functional groups are common and specific arrangements of atoms that
impart predictable reactivity and properties to a molecule. Even though there are
millions of organic compounds, you may be relieved to know that we can readily
understand much about whole families of compounds simply by learning about
the properties of the common functional groups. For example, all alcohols contain
an OH (hydroxyl) functional group attached to a saturated carbon bear- ing
nothing else but carbon or hydrogen. Alcohols as simple as ethanol in alcoholic
beverages and as complexas ethinyl estradiol in birth control pills have this
structural unit incommon. All aldehydes have a C(O) (carbonyl) group with one
bond to a hydrogen and the other to one or more carbons, such as in benzaldehyde
(from almonds). All ketones include a carbonyl group bonded by its carbon to one
or more other carbons on each side, as in the natural oil menthone, found in
geraniums and spearmint (Solomons, 2011: 91).
Alcohols are important because they can be converted into many other
types of compounds, iculding alkenes, haloalkanes, aldehydes, ketones, carboxylic
acids, and esters. Not only can alcohols be converted to these compounds, but
these compounds can also be converted to alcohols. But, these compounds can
also be converted to ol and use number to show that the compound is an alcohol,
changi the suffix –e of the parent alkane to ol. Hydroxyl groups are found in
carbohydrates and certain amino acids. Following are two representations for
glucose, the most abundant organic compound in nature. On the left is a Fischer
projection showing the confi guration of all chiral centers. On the right is a cyclic
structure, the predominant form in which this molecule exists in both the solid
form and in solution. The amino acid l-serine is one of the 20 amino acid building
blocks of proteins (Brown, 2012: 390).
Alcohols and alkyl halides are classified as primary, secondary, or tertiary
according to the classification of the carbon that bears the functional group. Thus,
primary alcohols and primary alkyl halides are compounds of the type RCH 2G
(where G is the functional group). Secondary alcohols and secondary alkyl halides
are compounds of the type RCH2G, and tertiary alcohols and tertiary alkyl halides
are compounds of the type R3CG. Many of the properties of alcohols and alkyl
halides are affected by whether their functional groups are attached to primary,
secondary, or tertiary carbons. A number of cases in which a functional group
attached to primary carbon is more reactive than one attached to a secondary or
tertiary carbon, as well as other cases in which the reserve true (Carey, 2000:
128).
The flavors and scents of nature include many examples of alcohols and
ethers. Menthol, found in peppermint oil, is an alcohol used both for flavoring and
for medicinal purposes. Vanillin, isolated from vanilla beans, contains an ether
functional group, as does anethole, the licorice flavor associated with fennel.
Ethanol, the alcohol produced by fermentation, is, of course, another flavor of
nature. Borneol, which can be isolated from artemesia, is an alcohol with a
fascinating molecular architecture. And eucalyptol, which shares the ending of its
name with other alcohols but is actually an ether, comes from eucalyptus leaves
(shown in the left photo above) and is used as a flavoring, scent, and medicinal
agent (Solomons, 2012: 502).
Presence of the polar –OH group alcohols are polar compounds with
partial positive charges on carbon and hydrogen and a partiel negative charge on
oxygen. The attraction between the positive of one dipole and the negative and of
another called dipole interaction. When the positive and of one the dipoles is a
hydrogen antom bonded to or N (atoms high of electronegativity) and the negative
and the other dipole is O or N atom, the attractive interaction between length
dipoles is particullary strong and is given the special name of hydrogen bounding.
The length of a hydrogen bond is water 177 pm, about 80% longer than an O-H
covalent bond. The presence of a large number hydrogen bond in liquid water,
however, has an important cumulative effect on the physical properties of water.
Because of hydrogen bonding, extra energy is required to separate each water
molecule from its neighbors, hence the relatively high boiling point water (Brown,
2012: 393).
These two rank among the most useful classes of organic compounds
because they often serve as starting materials for the preparation of numerous
other families. Two reactions that lead to alkyl halides will be described in this
chapter. Both illustrate functional group transformations. In the first, the hydroxyl
group because the of an alcohol ireplaced by halogen on treatment with a
hydrogen acyl halide ( Carey, 2000: 126).
Alcohols have a hydroxyl ( OH ) group bonded to a saturated carbon atom.
The alcohol carbon atom may be part of a simple alkyl group, as in some of the
following examples, or it may be part of a more complex molecule, such as
cholesterol. The alcohol carbon atom may also be a saturated carbon atom of an
alkenyl or alkynyl group, or the carbon atom may be a saturated carbon atom that
is attached to a benzene ring. The hydroxyl group has precedence over double
bonds and triple bonds in deciding which functional group to name as the suffix.
In common functional class nomenclature. alcohols are called alkyl alcohols such
as methyl alcohol, ethyl alcohol, and so on. Alcohols have much higher boiling
points than comparable ethers or hydrocarbons. Alcohol molecules can associate
with each other through hydrogen bonding, whereas those of ethers and
hydrocarbons cannot. Methanol, ethanol, both propyl alcohols, and tert-butyl
alcohol are completely miscible with water (Table 11.1). The remaining butyl
alcohols have solubilities in water between. The solubility of alcohols in water
gradually decreases as thehydrocarbon portion of the molecule lengthens; long-
chain alcohols are more “alkane-like” and are, therefore, less like water
(Solomons, 2012: 503-506).
The IUPAC rules permit alkyls halides to be named in two different ways
called functional class nomenclatur and substitive nomenclature. In fuctional class
nomenclature the alkyl group and the halide (fluoride, chlorid, bromide or iodide)
are designated as separate words. The alkyls group is named on the basis of its
longest continuous chain beginning at the carbon to which the halogen is attached.
CH3F CH3CH2CH2CH2CH2Cl CH3CH2CH CH2CH2CH3

Br

Methyl fluoride Pentyl chloride 1-ethyl bromide (Carey 2000: 127),

Concerning the evolution of conversion of t- butanol and selectivity of t-

buthyl chloride over different catalysts were plotted . as seen from figh 2, the
conversion of t- buthanol ncrease rapidly and first 5 h and then level of, which is
common for all reversible reaction. Also it is noted that the activity of the catalyst
as the first 2 h follows the orders , implying that the instrinstic catalytic activity of
all organicm a ammonium salt expect is superior to the inorganic salt, while for
the long tern performsance (Arjun, 2008).
This process is called stereconversion. Both SN 1 and SN2 reactions can
invert the chirality of a carbon center. N the SN1 mechanism departure of the
laving group generates approchiral intermediate which is then open to
nucleophilic attack on the either face. If both faces are equally impossible to the
nucleophilic this will result in racemisation on the molecule. In the case of the
SN2 reaction the nucleophilic will enter trygonal byprimidal intermedate steim
chemical. The Assuming the nucleophilic has the same precedence will be
inverted (Rao, 2015).

D. APPARATUS AND CHEMICAL

1. Apparatus
a. Distillation apparatus (1 set)
b. Separating funnel (1 piece)
c. Normal funnel (1 piece)
d. Graduated Cylnder 25 mL (1 piece)
e. Beaker flask 1000 mL (1 piece)
f. Erlenmeyer flask 250 mL (1 piece)
g. Spray bottle (1 piece)
h. Stative and clamp (1 unit)
i. Stopwatch (1 piece)
j. Cork (1 piece)
k. Rough wipe (1 piece)
l. Wipe smooth (1 piece)
2. Chemicals
a. Tertiary buthyl alcohol (C4H9OH)
b. Hydrochloric Acid (HCl)
c. Sodium bikarbonate acid 5% (NaHCO3)
d. Calcium Chloride anhydrous (CaCl2)
e. calcium sulphate (CaSO4)
f. Aquadest (H2O)
g. Filter Paper
h. Label
E. WORK PROCEDURES
1. Separated funnel was filled by 16 Ml of tertiary butanol
2. Separated funnel was added by 43 Ml of HCl consentrated
3. Mixture in separating funnel was stok time during 30 minutes and separated
funnel was opened when to decrease the pressure in separate funnel
4. Acid layer in the bottom was took and throw away
5. Halids (t- buthyl choride) was washed by 10 ml of NaHCO 3 5% then it was
shook during 5 minutes and the turbid layer was took and throw way
6. Halides (t- buthyl chloride) was washed by 10 ml of aquades, then it was
shook during 5 minutes and the residual sait in bottom layer was took and
throw away
7. Halides was poured into erlenmeyer flask and dried by CaCl2 anyhidrate
8. Halides was shook evenly
9. Halides in erlenmeyer flasic was filtered by funnel and filter paper to beaker
glass
10. Tertiary buthyl chloride was obtained and noted the volume 4 mL.
F. OBSERVATION RESULT
No Treatment Result
.
1. 16 ml tert- buthyl alcohol + - Hot
hydrochlorc acid - The color is yellow

2. The mixture is shaken for 20 - The mixtured is divided by two

minutes occasionally the layers
funnel valve is opened, then - There was bubble
let stand - The up layer was colorless
- The bottom layers was yellow

3. Mixured is washed it with 10 - The color changed and the

ml NaHCO3 5% up layer was murky and
bubble
- The bottom layer was
colorless
4. Mixtured is washed it with 10 - The color was changed and the
ml H2O up layer was murky
- The bottom layer was colorless
 5. Mixtured + direct with CaCl2 - The color was changed and the
anyhdrate up layers was murky
- The bottom was colorless

6. Mixtured is filtered The color is colorless, the

volume was 4 ml

G. DATA ANALYSIS
Known:
Volume of HCl : 42,5 ml
P (CH3)3 COH : 0,79 g/ml
Mr (CH3)3 COH : 74,9 g/mol
Mass (CH3)3 COH : 12,5 g
P HCl : 1,189 g/ml
Mr HCl : 36,5 g/mol
P (CH3)3 CCl : 92,5
Volume (CH3)3 CCl : 1,5 ml
Asked Rendemant ?
Answer:
m
P =
v
m
v =
p
12,5 g
v =
0,79 g / mol
= 15,8 ml
m(CH 3)3 COH
Volume (CH3)3 COH =
Mr(CH 3) 3 COH
12,5 g
=
0,778 g /mol
= 16 mL
Mass of HCl = v HCl . p HCl
= 42,5 ml . 1,38 g/ml
 = 50,15 g
mof HCl
Mol HCl =
Mr HCl
50,15 g
=
36,5 g /mol
= 1,37 mol
(CH3)3 COH(aq) + HCl(aq) (CH3)3 CCl(aq) + H2O(l)
Initial 0,17 mol 1,37 mol -
Reaction 0,17 mol 0,17 mol 0,17 mol 0,17 mol
Remain - 1,2 mol 0,17 mol 0,17 mol
Mass theory of (CH3)3 CCl:
Mol (CH3)3 CCl . Mr (CH3)3 CCl
= 0,77 mol . 0,25 g/mol
= 15,72 g
Mass experiment of (CH3)3 CCl
= Mol (CH3)3 CCl . Mr (CH3)3 CCl
= 4 ml . 0,84 g/mol
= 3,36 g
mass experiment 3,36 g
% rendment = = x 100% = 21,37%
mass theory M 15 , 72 g
H. DISCUSSION
Tertier butil klorida adalah salah satu senyawa halogen organik dengan
rumus (CH3)3CCl. Senyawa ini adalah cairan yang tidak berwarna dan mudah
terbakar. Tertier butil klorida adalah senyawa akil halide tersier karena
mempunyai gugus alkil yang terikat pada karbon ujung (sebuah halogen yang
terikat pada suatu atom C primer). Senyawa ini sedikit larut dalam air, dengan
kecenderungan untuk menjalani hidrolisis ke tert-butil alkohol yang sesuai.
Pembuatan tertier butil klorida dapat melibatkan reaksi nukleofilik jenis reaksi
SN1. Konsep yang digunakan untuk membahas reaksi nukloefilik adalah konsep
putus/pembentukan ikatan heterolitik (Chang, 2010: 109-110 & 115). Tujuan dari
percobaan ini adalah dapat mengetahui cara penysunan dan penggunaan alat yang
digunakan dalam pembuatan senyawa organik berwujud cair seperti merefluks,
ekstraksi pelarut, menggunakan corong pisah, pengeringan, penyaringan dan
destilasi, asas-asas reaksi substitusi nukleofilik alifatik dan perbedaan yang khas
antara substitusi jenis SN1 dan SN2.
Reaksi SN1 adalah sebuah reaksi substitusi dalam kimia organik. SN1
adalah singkatan dari substitusi nukleofilik dan "1" memiliki arti bahwa tahap
penentu laju reaksi ini adalah reaksi molekul tunggal. Reaksi ini melibatkan
sebuah zat antara karbokation dan umumnya terjadi pada reaksi alkil halida
sekunder ataupun tersier (Chang 2010: 117 ).
Reaksi SN1 antara molekul A dan nukleofil B memiliki tiga tahapan:
1. Pembentukan sebuah karbokation dari A dengan pemisahan gugus lepas
dari karbon; tahap ini berjalan dengan lambat dan reversibel.
2. Serangan nukleofilik: B bereaksi dengan A. Jika nukleofil tersebut adalah
molekul netral (contoh: pelarut), tahap ketiga diperlukan agar reaksi ini
selesai. Jika pelarutnya adalah air, maka zat antaranya adalah ion oksonium.
3. Deprotonasi: Penyingkiran proton pada nukleofil yang terprotonasi oleh
ion ataupun molekul di sekitar.
Menurut Chang (2010), Pembuatan tertier butil klorida data terjadi karena
reaksi antara tertier butil alkohol dengan HCl. Pemutusan suatu ikatan dapat
menghasilkan orbital isi kosong, sedangkan pembentukan ikatan dapat dilihat dari
persamaan reaksi berikut:

C 4H 9O H + H Cl C 4H 9O H + H 2O

Tahap pertama : Pembentukan sebuah karbokation dengan pemisahan gugus pergi

CH 3 CH 3

+ -
C H 3 C O H C H 3 C + O H

CH 3 C H 3

Tahap kedua : serangan nukleofil

+
H Cl H + C l-
 CH 3 CH 3

+
CH 3 C + C l- CH 3 C Cl + H +
O H -

CH 3 CH 3

Bentuk umum dari reaksi di atas adalah

N: + R―X → R ―Nu + x:
Dengan Nu menandakan nukleofil menandakan pasangan elektron serta
R―X menanadakan subtrat dengan gugus pergi x. Pada reaksi tersebut, pasangan
elektron dari nukleofil menyerang subtrat membentuk ikatan baru, sementara
gugus pergi melepaskan diri bersama dengan sepasangan elektron. Produk
utamanya R―Nu. Nukleofil dapat mememiliki dapat memiliki muatan listrik
negatif ataupun netral, sehingga produk yang di hasilkan biasanya netral atau
bermuatan positif dan pada yang terjadi pada rteaksi diatas adalah produk yang
netral. Reaksi tersebut menunjukkan bahwa tertier butil alkohol akan terurai
menjadi ion (CH3)C+ dan OH, sedangkan HCl akan terurai menjadi H+ dan Cl-. Ion
(CH3)C+ akan bersatu dengan Cl- membentuk (CH3)CCl (tertier butil klorida) dan
ion OH- akan bergabung dengan H+ membentuk air (H2O).
Pembuatan tertier butil klorida dapat dilakukan dengan mereaksikan tertier
butil alkohol dengan asam klorida. Tujuan dari pembuatan senyawa organik
berwujud cair, memahami asas-asas substitusi nukleofilik dan perbedaan reaksi
SN1 dan SN2. Perlakuan pertama adalah mencampurkan tertier butil alkohol
dengan asam klorida ke dalam corong pisah. HCl pekat berfungsi sebagai reaktan
untuk menghasilkan tertier butil klorida yang bersifat nukleofilik yaitu ion Cl –
yang akan menyerang masuk ke gugus tertier butil alkohol. Tertier butil alkohol
berfungsi sebagai pembentuk alkil. Campuran antara tertier butil alkohol dan asam
klorida berwarna bening.

Campuran yang berada pada corong pisah selanjutnya dikocok selama 20

menit dengan kecepatan konstan agar pemisahan lebih maksimal. Prinsip corong
pisah adalah memisahkan larutan atau campuran berdasarkan massa jenis dan sifat
kepolaran suatu zat. Adapun tujuan pengocokan adalah menyempurnakan proses
reaksi dan mengakibatkan tekanannya menurun. Tertier butil klorida bersifat
nonpolar sedangkan air bersifat polar. Massa jenis air adalah 1g/mL, sedangkan
massa jenis tertier butil klorida adalah 0,84 g/mL.
Semakin maksimal pengocokan maka akan semakin banyak hasil yang
diperoleh. Selama pengocokan berlangsung, sesekali tutup corong pisah
dilonggarkan agar dapat menurunkan tekanan dalam corong pisah akibat
pengocokan sehingga corong pisah tidak meledak akibat pengocokan. Produk
yang dihasilkan dari percobaan ini adalah tertier butil klorida dan air. Setelah
pengocokan corong pisah didiamkan selama beberapa menit hingga terbentuk dua
lapisan. Lapisan atas adalah terter butil klorida, sedangkan lapisan bawah adalah
air. Terbentuknya dua lapisan karena perbedaan sifat kepolaran antara tertier butil
klorida dan air selain itu karena perbedaan massa jenis dari kedua zat tersebut.
Tertier buti klorida bersifat nonpolar, sedangkan air bersifat polar sehingga kedua
zat tersebut tidak mampu untu saling melarutkan. Tertier butil klorida berada pada
lapisan atas karena massa jenisnya lebih kecil daripada air sehingga air berada
pada bagian bawah.
Perlakuan selanjutnya yaitu lapisan bawah berupa air pada corong pisah
dibuang sedangkan larutan atas (Tertier butil klorida) diambil dan dicuci dengan
NaHCO3 di dalam corong pisah. Penambahan NaHCO 3 bertujuan untuk mengikat
sisa-sisa halida yang terdapat pada campuran tersebut. NaHCO 3 dapat mengikat
sisa HCl karena sifat antara NaHCO 3 dan HCl sama-sama polar. Pada proses
pencucian ini akan terbentuk dua lapisan. Lapisan atas adalah halida dan lapisan
bawah adalah garam yang larut dalam air. Reaksi yang terjadi adalah sebagai
berikut:
NaHCO3 (aq) + HCl (aq)            —>      NaCl (aq) + H2O + CO2(g)
Setelah itu lapisan bawah dibuang dan lapisan atas dicuci lagi dengan air
yang bertujuan untuk memisahkan garam yang terdapat pada halida serta
melarutkannya. Kemudian terbentuk dua lapisan. Lapisan bawah yang
mengandung air dan garam dibuang, sedangkan lapisan atas yang berupa tertier
butil klorida diambil dan dimasukkan kedalam gelas kimia yang telah berisi CaCl 2
anhidrat. Tujuan penambahan CaCl2 anhidrat adalah untuk mengikat air yang
masih tersisa dalam halida tersebut. Masih adanya air dalam halida dengan
larutnya CaCl2 tetapi setelah air terikat oleh CaCl2 maka akan terbentuk endapan
putih karena CaCl2 telah mengikat air tetapi jumlah molekul CaCl2 lebih banyak
dari pada air sehingga terjadi pengendapan. CaCl 2 dapat mengikat air karena
sifatnya polar begitu juga dengan air yang bersifat polar. Reaksi yang terjadi:
CaCl2 + x H2O       —>    CaSO4 x H2O
Larutan yang telah dikeringkan didekantasi melalui corong biasa yang
dilengkapi dengan kertas saring berlipat agar larutan yang bercampur dengan
CaCl2 benar-benar terikat dengan H2O atau sisa asam sehingga didapatkan tertier
butil klorida yang murni sebanyak 4 mL. Rendemen yang diperoleh adalah 8 %
menunjukkan perbandingan antara hasil percobaan dengan hasil yang seharusnya
diperoleh sangat jauh sehingga proses destilasi tidak terjadi karena yang
dihasilkan sangat sedikit. Hal ini dapat terjadi karena kecepatan saat pengocokan
yang tidak konstan dan arah pengocokan yang berlainan. Selain kurangnya
penguasaan konsep yang dimiliki praktikan.

I. CONCLUSION
1. In the manufacture or tertier buthyl chloride was carried out two separation
techniques namely drying and filtering
2. Reaction is a nucleophilic aliphatic substitution reaction because of an attack
nucleophilic on a straigh chain organic compounds. Where the nucleophilic
substitution is influenced by the molecular structure of the type nucleophilic,
the group went and solven effects
3. The mechanism reaction of SN2 jusc occur alkyl halide primary and secondary.
For mechanism reaction of SN1 jus occur in alkyl halyde tersier.
J. SUGGESTION
For apprentice do not be late, be careful when do the experiment, always
coordination to do something and also have more knowledge about work
procedure, and dont bed noise when practcum occur and always coordination with
their friends.
 BIBLIOGRAPHY

Aijun, S. Nie, y., Chanxi L, and Wany, Z. 2008. Preparation of Buthyl Chloride
Fro Butanol and Hydrochloric Acid using Ionic Liquids as Catalyst. Journal
of Chemical Engineering. 16(1):

Brown, W., Christopher S., Brint, L and Eric, L. 2012. Organic Chemistry (sixth
edition). USA: Pra Media GlobaL.

Carey, F. 2000. Organic Chemistry (fourth edition). USA: MC Graw Hill.

Rao, P, Venkateswara, A. V. G. S. Prasad, and P. S. S. Prasad. 2015. Synthesis

and Application of Schiff base in resolution-racemization of Primary
Amines. International Journal of Medicine and Pharmaeutical Research.
3(2).

Solomons, T, W, Graham and Craig B. Frayhile. 2011. Organic Chemistry. USA.

John Wiley.
 ANSWER OF QUESTION

1. N- buthyl alcohol and see buthyl alcohol can not be converted into chloride if
only shake with concentrated HCl because it has properties that are very
difficult to dissolve in water., but n-buthyl alcohol and sec buthyl alcohol can
be converted into chlorides if done heating (high temperature) and using HCl
catalyst for reacting with n-buthyl alcohol and sec buthyl alcohol.
2. Acid halides are very casy to react with alcohol to form halide is iodide since
iodide ions most easily replaced in a nucleophylic substitution reaction
because the iodide ions is a neak base so that the iodide ion is a good leaving
group.
3. If the t- buthyl alcohol is heated with NaOH then be generated alkoxide salt.
As for the reaction then take place namely
H3C–C–O– H+ +Na+-OH H3C–C– O–Na-H2O H2O + (C(CH3) ONa

H3C