CONFIDENTIAL

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SULTAN IDRIS EDUCATION UNIVERSITY

UNIVERSITI PENDIDIKAN SULTAN IDRIS

FINAL EXAMINATION
SEMESTER 1 SESSION 2019/2020

COURSE : SKO3023 COURSE : ORGANIC CHEMISTRY 1

: 0 2 JAN 2020 DURATION : 2 HOURS
DATE

INSTRUCTIONS
1. This question paper contains FOUR questions.
2. Answer ALL questions.
3. Questions must be answered in the ANSWER BOOKLET provided.
4. Please DO NOT use pencil.

This question paper contains 4 pages including the cover page

PROGRAMME:

YEAR: LECTURE GROUP: A/B

REGISTRATION NO. :

IDENTITY CARD NO. :

LECTURER : DR. WAN MOHD NUZUL HAKIMI W SALLEH

DO NOT OPEN THIS QUESTION PAPER UNTIL

YOU ARE TOLD TO DO SO

CONFIDENTIAL
SKO3023 Organic Chemistry 1 2

ANSWER ALL QUESTIONS

(50 MARKS)

1. (a) Define the following terms with the appropriate example.

(0 Diastereomer

(■•) Meso compound

(iii) Constitutional isomer

[6 Marks]

(b) Draw the structures for each of the following compounds.

(i) spiro[5.4]decane

C<i) bicyclo[4.1.0]heptane

(iii) 1,3-dimethylbicyclo[3.3.1]nonane

[3 Marks]

(c) Write the structures of two chair conformations of fraz7s-4-chloro-1-

propylcyclohexane. Which conformation is more stable? Explain.

[4 Marks]

[See next page

SKO3023 Organic Chemistry 1 3

2. (a) Choose and explain which of the following pairs would have the higher boiling
points.

(i) Hexane and 2-methylpentane

(ii) 1-Butanol and butane

[4 Marks]

(b) Proposed complete mechanism for the following reactions.

HBr Br

(i)
[3 Marks]

H2O / H+ OH

(ii)
[3 Marks]

•Cl
Cl2, CCI4

(iii) Cl
[3 Marks]

(c) Give the product formed when 1-methylcyclohexene reacts with the following
reagents:

(i) H2SO4

(ii) KMnO4

(iii) O3, Zn / H3O+

[3 Marks]

(See next page

 SKO3023 Organic Chemistry 1 4

3. (a) By using Sn1 or Sn2 reaction, write complete mechanism for the conversion of
1-bromopropane to propanol.
[2 Marks]

(b) By using an appropriate chemical equation, show how the following conversions
can be accomplished.

(>) 1-Hexyne to 1-hexene

(ii) 1-Hexyne to pentanoic acid

[4 Marks]

(c) Write equations to show the following conversion. Provide suitable reagents
for the reaction. (Note: The conversion required more than one step of reactions).

ch3i > ch3cooh

lodomethane Ethanoic acid

[3 Marks]

4. (a) Consider the following reaction scheme.

H2SO4
A + B
180°C

(i) Draw the structures of compounds A and B.

Identify the major product.
[2 Marks]

(ii) Proposed a mechanism for the formation of major product.

[6 Marks]

(b) Devise a synthesis of the alkene C using 2-bromobutane as starting materials.

Show all relevant reagents. (Note: The conversion required more than one step of
reactions).

[4 Marks]

END OF QUESTIONS