[KOT 121]

INDEX NO:- ----------------------------

UNIVERSITI SAINS MALAYSIA

First Semester Examination

2011/2012 Academic Session
January 2012

KOT 121 – Organic Chemistry I

[Kimia Organik I]

Duration: 3 hours
[Masa : 3 jam]

Please check that this examination paper consists of THIRTY NINE pages of printed
materials before you begin the examination.
Instructions:
PART A (40 marks), comprising 40 multiple-choice questions (MCQ), has to be
answered within the first hour of the examination on the OMR forms provided. The
completed OMR forms will be collected one hour after the commencement of the
examination.
PART B (60 marks) consists of essay-type questions. Answer only THREE (3)
questions.
Answer each question on a new page.
You may answer either in Bahasa Malaysia or in English.
Ensure that your OMR form is complete [with your index number, course code, answers
to the questions]. Use only a 2B pencil on your OMR form.
Submit the answer scripts and question paper to the Invigilator before you leave the
Examination Hall at the end of the examination.

In the event of any discrepancies, the English version shall be used.

…2/-
 [KOT 121]

-2-
SECTION B (60 MARKS)

Answer any THREE (3) questions

1. (a) Draw both chair conformations for menthol and its stereoisomer,
neomenthol. Which groups are axial and which groups are equatorial?
Explain which conformation is more stable for each stereoisomer.

CH3 CH3

OH OH
CHCH3 CHCH3
CH3 CH3

Menthol Neomenthol

(6 marks)

(b) Draw Newman projections for the anti and gauche conformations about
the C─C bond of the following compounds. What other factors, besides
steric and torsional strain, influence the stability of these conformations?

(i) 1,2-Dichloroethane

(ii) 1,2-Ethanediol
(8 marks)

(c) A solution of 0.2 gmol-1 of a compound in a 1.0 dm cell rotates plane-

polarized light +13.3° at the sodium D line.

(i) What is the specific rotation of this compound?

(ii) What is the rotation caused by a solution of 0.1 g of this compound

in 10 mL of solution?

(iii) Suppose a solution of a compound gave a rotation of +160°. How

could this rotation be distinguished from one of -200° and from one
of +520°?

(6 marks)

…17/-
-17-
 [KOT 121]

2. (a) What is the hybridization of each of the carbon and oxygen atoms in the
following compounds?

O
C OCH2CH3

CH3

A B

(2 marks)

(b) Which H atom in vitamin C (ascorbic acid) is the most acidic. Explain
your answer.

(2 marks)

(c) Draw the two chair conformers for each of the following, and indicate
which conformer is more stable:

(i) trans-1-Ethyl-2-isopropylcyclohexane

(ii) trans-1-Ethyl-2-methylcyclohexane.
(4 marks)

(d) Propose a mechanism for the following reaction:

(4 marks)

…18/-
-18-
 [KOT 121]

(e) Explain why (CH3)3CO- is a stronger base than CH3CH2O-.

(2 marks)

(f) Draw the products formed when each of the following alkenes is treated
with HBr.

(i)

(ii)

(iii)

(3 marks)

(g) Give the IUPAC name of all alcohols having four carbon atoms and
classify them into either 1°, 2° or 3° alcohol.

(3 marks)

…19/-
-19-
 [KOT 121]

3. (a) What is the product A and the reagents involve in the following reactions?

(8 marks)

(b) Reaction of HBr with 1-ethylcyclohexene would produce 1-bromo-1-

ethylcyclohexane but not 1-bromo-2-ethylcyclohexane. Explain this
statement.
(6 marks)

(c) Give the products of each of the reaction below:

(i)

(ii)

(iii)

(6 marks)

…20/-
-20-
 [KOT 121]

4. (a) Unsymmetrical ethers can be prepared via the Williamson ether synthesis
from alkyl halides by SN2 reactions using strong nucleophiles. Explain
why the unsymmetrical ether below cannot be synthesized via the
Williamson ether synthesis.

(3 marks)

(b) Provide the major organic product of the reaction below and a detailed,
stepwise mechanism which accounts for its formation.

(5 marks)

(c) Draw a stepwise SN1 or E1 mechanism to illustrate how the four products
are formed in the following reaction:

(6 marks)

(d) Draw the steps involved in the dehydration of the following alcohols to the
alkenes:

(i)

(ii)

(iii)

(6 marks)

…21/-
-21-
 [KOT 121]

TERJEMAHAN

Arahan:

BAHAGIAN A (40 markah, mengandungi 40 soalan objektif (MCQ), perlu dijawab

dalam masa 1 jam pertama di dalam borang jawapan OMR yang disediakan.
Borang OMR akan dikutip 1 jam selepas peperiksaan bermula.

BAHAGIAN B (60 markah), mengandungi soalan bertulis. Jawab hanya TIGA (3)
soalan sahaja. Jawab setiap soalan di muka surat yang baru.

Anda dibenarkan menjawab soalan ini sama ada dalam Bahasa Malaysia atau Bahasa
Inggeris.

Pastikan borang OMR diisi dengan lengkap [nombor angka giliran, kod kursus, jawapan].
Gunakan hanya pensil 2B bagi borang OMR.

Sila serahkan buku jawapan dan kertas soalan ini kepada pengawas sebelum anda keluar
dari dewan peperiksaan.

Sekiranya terdapat sebarang percanggahan pada soalan peperiksaan, versi Bahasa

Inggeris hendaklah diguna pakai.

...22/-
-22-
 [KOT 121]

BAHAGIAN B (60 MARKAH)

Jawab TIGA (3) soalan.

1. (a) Lukis kedua konformasi kerusi untuk mentol dan stereoisomernya,

neomentol. Kumpulan mana aksial dan yang manakah ekuatorial?.
Jelaskan konformasi mana lebih stabil bagi setiap stereoisomer.

CH3 CH3

OH OH
CHCH3 CHCH3
CH3 CH3

Mentol Neomentol

(8 markah)

(b) Lukis projeksi Newman bagi konformasi anti dan gaus berkenaan ikatan
C─C sebatian berikut. Apakah factor lain, selain sterik dan tegangan
torsional menyumbangkan kestabilan konformasi?

(i) 1,2-Dikloroetana
(ii) 1,2-Etanadiol
(6 markah)

(c) Larutan 0.2 gmol-1 sebatian dalam 1.0 dm sell memutar cahaya
terpolarisasi - bidang +13.3° pada garis D sodium .

(i) Apakah putaran spesifik sebatian ini?

(i) Apakah putaran yang menyebabkan larutan 0.1 g sebatian ini
dalam larutan 10 mL ?
(ii) Larutan suatu sebatian memberikan putaran +160°. Bagaimana
putaran ini di kenalpasti dari -200° dan dari +520°?
(6 markah)

…36/-

-36-
 [KOT 121]

2. (a) Apakah penghibridan setiap atom karbon dan oksigen dalam sebatian
berikut?

O
C OCH2CH3

CH3

A B

(2 markah)

(b) Manakah atom H dalam vitamin C (asid ascorbik) yang paling berasi?
Jelaskan jawapan anda.

(2 markah)

(c) Lukis dua konfomer kerusi setiap berikut, dan tentukan konfomer mana
yang lebih stabil:

(i) trans-1-Etil-2-isopropilsikloheksana
(ii) trans-1-Etil-2-metisikloheksana
(4 markah)

(d) Cadangkan mekanisme setiap tindak balas berikut:

(4 markah)

…37/-
-37-
 [KOT 121]

(e) Terangkan mengapa (CH3)3CO- adalah bes yang lebih kuat daripada
CH3CH2O-.

(2 markah)

(f) Lukiskan hasil yang terbentuk apabila setiap alkena berikut diolah oleh
HBr.

(i)

(ii)

(iii)

(3 markah)

(g) Berikan nama IUPAC bagi semua alkohol yang mengandungi lima atom
karbon dan mengkelaskannya kepada samada alkohol 1°, 2° atau 3°.

(3 markah)

…38/-
-38-
 [KOT 121]

3. (a) Apakah hasil A dan reagen yang terlibat dalam tindak balas berikut?

(8 markah)

(b) Tindakbalas HBr dengan 1- metilsikloheksena akan menghasilkan 1-

bromo-1-metilsikloheksana bukan 1-bromo-2- metilsikloheksana.
Terangkan kenyataan ini.

(6 markah)

(c) Beri hasil tindak balas dibawah:

(i)

(ii)

(iii)

(6 markah)

…39/-
-39-
 [KOT 121]

4. (a) Eter tak-simetri boleh disediakan melalui sintesis eter Williamson daripada
halida alkil dan nukleofil yang kuat dengan tindak balas S N2. Terangkan
mengapa eter tak-simetri yang berikut tidak boleh disediakan melalui
sintesis eter Williamson .

(3 markah)

(b) Berikan hasil organik utama bagi tindakbalas berikut dan suatu
mekanisme terperinci yang menerangkan pembentukannya.

(5 markah)

(c) Lukiskan suatu mekanisme berlangkah SN1 atau E1 untuk menunjukkan

pembentukan empat hasil yang terbentuk dalam tindak balas yang berikut:

(6 markah)

(d) Lukiskan langkah-langkah yang terlibat dalam pengdehidratan alkohol

yang berikut kepada alkena:

(i)

(ii)

(iii)

(6 markah)

-oooOooo-