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UNIVERSITI PENOIOIKAN SULTAN lORIS

FINAL EXAMINATION
SEMESTER 1 SESSION 2016/2017

CODE: SK03023 COURSE: ORGANIC CHEMISTRY I

DATE: 0 3 JAN 2017 DURATION: 2 HOURS

INSTRUCTIONS

1. This question paper contains FOUR (4) structural questions.

2. Answer ALL questions in the answer booklet provided. Please DO NOT use pencil.

This question paper contains 3 pages including the cover page

NAME:

-
YEAR: LECTURE GROUP: A I B

REGISTRATION NO: I I I I I I I
IDENTITY CARD NO :
I I I I I I I I I I I I I
LECTURER: PM. DR. KARTINI AHMAD

DO NOT OPEN THIS QUESTION PAPER UNTIL YOU ARE TOLD TO DO SO

SK03023 Organic Chemistry I 2

ANSWER ALL THE FOLLOWING QUESTIONS.

1. (a) Refer to the following reaction scheme:

KMn04, H+ r(YCH(Br)CH3
A
11 �
l-(Bromoethy I)benzene

je
r(YCH=CH2
�
Styrene

(i) Draw structure of A.

(ii) Give reagents Band C.

(iii) Name the reactions to form 1-(bromoethyl)benzene from ethylbenzene

and styrene from 1-(bromoethyl)benzene.

[5 Marks]

The following compounds undergo nitration reaction.

(b)

o
II

VCCH3
Compound I Compound II

Give the name for one of the compounds above.

(i)
(ii) State the reagent for nitration.

(iii) Draw the product(s) of nitration for each of the above compounds.
from benzene, show the complete mechanism of reaction for the
(iv) Starting
formation of compound II.

[10 Marks]

[See next page

SK03023 Organic Chemistry I 3

2. Reaction between 2-methylcyclohexanol and concentrated sulphuric acid produce two

(2) different products with the same molecular formula.

D + E

OH

i) Give the IUPAC name and draw the structure of D and E. Identify the major
product?
[5 Marks]

ii) Propose the mechanism for the formation of major compound.

[6 Marks]

3. Consider the following reactions scheme.

F G H
...
(major product)

i) Give reagents F and H and the structure of G. Give IUPAC name for G.

ii) Show all steps in the formation of G.

iii) Give a simple chemical test to distinguish between butane and 2-butene. State

the observation and write the chemical equation.

[20 Marks]

Write the chemical equations when 2-methyl-2-butene reacts with the following
4. complete
reagent(s).

i) KMn04, cold

ii) KMn04/H+, heat

iii) HBr
[4 Marks]

END OF QUESTIONS