UNIVERSITI TEKNOLOGI MALAYSIA

FACULTY OF SCIENCE
……………………………………………………………………………………………………………….

TEST 2
SEMESTER II SESSION 2018/2019

COURSE CODE : SSCC 1603/SSCK 1603

COURSE NAME : ORGANIC CHEMISTRY-FUNCTIONAL GROUPS

PROGRAMME : 1 SSCC/ 1 SSCA/ 1 SKTB

LECTURERS : ASSOC. PROF. DR. ZAINOHA ZAKARIA

DR. JOAZAIZULFAZLI JAMALIS
DR. KHAIRIL JUHANNI ABD KARIM

DATE : 25 APRIL 2019

DURATION : 1 HOUR 15 MINUTES

INSTRUCTION : ANSWER ALL QUESTIONS IN THE SPACE GIVEN

IN THE QUESTION BOOKLET.

NAME :

SECTION :

LECTURER :

(THIS QUESTION PAPER CONSISTS OF FIVE (5) PRINTED PAGES INCLUDING THIS PAGE)
 SSCC 1603/ SSCK 1603

QUESTION 1 (14 MARKS)

a) The following alcohols were each treated with Lucas reagent (HCl/ZnCl2) to form
substituted products.

OH OH OH OH
OH

i. Arrange the alcohols in the order of increasing reactivity towards Lucas reagent.
ii. Explain your answer by giving appropriate structures as evidence.

(4 marks)

b) Suggest a stepwise mechanism for the following elimination reaction.

OH + H2 O
(3 marks)

-2-
 SSCC 1603/ SSCK 1603

c) Give reagents A, B and C and products D, E, F and G in the following reaction

schemes.

OH

OH
G
A C
SOCl2

O OH O
B OH , H+ D
OH OH

Br2/H2O NaOH

F E
(7 marks)

-3-
 SSCC 1603/ SSCK 1603

QUESTION 2 (16 MARKS)

a) Using the starting material butyne and any appropriate reagents, suggest how you would
synthesize the product as shown below.

CH3CH2 C CH CH3CH2 C CCH2CH2OH

(2 marks)

b) An unsymmetrical ether, n-propyl phenyl ether was prepared via Williamson synthesis
method.

i. Draw the structural formula of the ether.

ii. Give IUPAC name for the ether.
iii. Show how you would synthesize the ether using suitable alcohols.
iv. What are the products if the ether reacts with excess HBr.

(5 marks)

-4-
 SSCC 1603/ SSCK 1603

c) Give the reagents from H to K in the following reaction schemes.

OCH3 OH
OH OCH3
H K
O
OH I J
OH
OH

(4 marks)

d) Ethers and alcohols can be isomeric to each other. Write the structures and give IUPAC
names for all possible isomers (ethers and alcohols) with the molecular formula C4H10O.

(5 marks)

-5-