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(This Question Paper Consists of Seven (7) Printed Pages Including This Page)

This document is a test paper for Organic Chemistry - Functional Groups consisting of 7 pages with two questions. Question 1 has parts (a) through (d) requiring the drawing of structural isomers, identification of reaction products, and outlining a synthetic route. Question 2 has parts (a) through (c) requiring the labeling of compounds as aromatic/non-aromatic, arranging compounds by reactivity, and identifying a reagent and reaction mechanism. The test was administered on May 13, 2019 at Universiti Teknologi Malaysia for 1 hour and 15 minutes.

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70 views7 pages

(This Question Paper Consists of Seven (7) Printed Pages Including This Page)

This document is a test paper for Organic Chemistry - Functional Groups consisting of 7 pages with two questions. Question 1 has parts (a) through (d) requiring the drawing of structural isomers, identification of reaction products, and outlining a synthetic route. Question 2 has parts (a) through (c) requiring the labeling of compounds as aromatic/non-aromatic, arranging compounds by reactivity, and identifying a reagent and reaction mechanism. The test was administered on May 13, 2019 at Universiti Teknologi Malaysia for 1 hour and 15 minutes.

Uploaded by

aiza
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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UNIVERSITI TEKNOLOGI MALAYSIA

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

TEST 1
SEMESTER II SESSION 2018/2019

COURSE CODE : 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 : 13 MAY 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 SEVEN (7) PRINTED PAGES INCLUDING THIS PAGE)
SSCC 1603/ SSCK 1603

QUESTION 1 (18 MARKS)

(a) Five (5) structural isomers have molecular formula of C6H14.

i. Draw the structure of all isomers.


ii. Which isomer has the lowest boiling point? Explain your answer.

[4 marks]

-2-
SSCC 1603/ SSCK 1603

(b) Give the products of A to F in the following reaction scheme.

A Cl

KOH

O
KMnO4 i. B2H6 in THF
C + H3C C OH B F
(major product) ii. H2O2, NaOH

Cl2 / H2O H2O/H+

D E

[6 marks]

-3-
SSCC 1603/ SSCK 1603

(c) The following reaction forms three (3) products and one of the products has been given.

CH3 H2SO4 CH2


OH G + H +

i. Draw the structures of G and H.


ii. Write the name of the reaction.
iii. Propose the reaction mechanism to form all products.
iv. Identify the major product and give reason.

[5 marks]

-4-
SSCC 1603/ SSCK 1603

(d) Show the synthetic route for the synthesis of 3-octyne by using 1-butene as the only
organic starting material.

[3 marks]

QUESTION 2 (12 MARKS)

(a) Label each of the following compounds as aromatic, non aromatic or anti-aromatic. Justify
your answer.

H
N
i. ii. Iii. iv.
O

[4 marks]

-5-
SSCC 1603/ SSCK 1603

(b) Arrange the following compounds in the order of increasing reactivity towards
electrophilic substitution reaction and give reason.

O CH3
C NH2 CH3

, ,

[3 marks]

-6-
SSCC 1603/ SSCK 1603

(c) Consider the following reaction.


CH3
reagent J

i. Give reagent J.
ii. Write the name of the reaction.
iii. Propose the reaction mechanism.

[5 marks]

-7-

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