UNIVERSITI KUALA LUMPUR

MALAYSIAN INSTITUTE OF
CHEMICAL & BIOENGINEERING TECHNOLOGY

ORGANIC CHEMISTRY
(CLD 10302)
JAN 2013
Assignment 1

1. Vanillin is main constituent of vanilla flavouring. Predict the product of its reaction
with KMnO4 in aqueous KOH. ( 3 MARKS)
2. Provide the products from the reactions. ( 3 MARKS).

i.
CH 3

H2SO4
+ HNO3

ii.

AlCl3
+ CH3Cl

iii.

CH 3

FeBr3
+ Br2
ORGANIC CHEMISTRY CLD 10302

3. Give the correct IUPAC name for each of the following. ( 7 MARKS)
a.
CH3 CH2CH3
H H2 H2 H2 H2
CH3 C C C C C C C C CH3
H2 H
CH3 CH2CH2CH3

H2C CH3
b. H2 H
CH3 C C C CH2
H H2 H2
CH3 HC C C CH3
H2C CH3

Br

c. H3CH2C

CH3CH2CH2 CH2CH2CH3
C=C
d. H H

CH3CHCH2C CCHCH3

e. Cl CH3

OH

f. CH2 CH 3

2
ORGANIC CHEMISTRY CLD 10302

Br CH3

g. NO2

4. Determine the product of the synthesis of 1 mol of 2,3-dichlorobutane in presence

of excess of sodium amide? (2 MARKS).

5. What is the product that would be obtained from the following reactions of alkynes?
(3 MARKS).

CH3CH2C
+ H2
excess
a) CCH2CH2CH3

HC
+ HCl
excess
b) CCH2CH2CH3

HC
+ Br2
excess
c) CCH2CH2CH3

6. Write structures formula for the following compounds. (20 MARKS).

1. 3-ethyl-5-isobutyl-3- 2. isopropylbenzene
methylnonane

3. tert-butylbenzene 4. 1,1,2-trimethylcyclopentane

5. 2-methyl-1,3-butadiene 6. Trans-4-ethyl-3-heptene

7. Z-1,2-dibromoethene 8. 3-phenyl-1-pentyne

9. p-bromophenol 10. 4-tert-butyl-2-methylheptane

11. 2-ethyl-4-propylcyclohexanone 12. 2,5-hexanedione

13. ethyl 2-chloropropanoate 14. 3-(2-chloroethoxy)-1-butanol

15. 2-hydroxy-2-phenylethanoic acid 16. 2,4-dimethyl-3-pentanol

17. 1-chloro-2,4-dinitrobenzene 18. 1,2,4-tribromobenzene

19. 3,4-dichloro-1-hexyne 20. 6-bromo-2-methyl-3-heptyne

3
ORGANIC CHEMISTRY CLD 10302

7. Give the reagents that would be required to carry out the following reactions
and syntheses. (7 MARKS)

SYNTHESIS OF ALKENES REACTION OF ALKENES

CH2CHCH2Br

CH2CH2CH3 Br

CH2CH2CH3
CH2CH=CH2
CH2CHCH3

OH

CH2CHCH3

CH2CH2CH2Br Br

CH2CHCH3

OH

TOTAL MARKS: 45 MARKS