UNIVERSITY OF ZULULAND

FACULTY OF SCIENCE AND AGRICULTURE

DEPARTMENT OF CHEMISTRY
SCHM 212 (ORGANIC CHEMISTRY): TEST 2
Examiner: Dr SE Mavundla
September 2015

07

Duration: 1.5 hr
Marks: 60

Total

Question 1 (9 marks)
Define the following terms and give examples of each. (3 marks each)
1.1.

Enantiomers

Stereoisomers which are non-superimposable mirror images of each

other
H
H3C

H
OH

HO

1.2.

CH3

Constitutional isomers

Are molecules with the same molecular formula but different

connectivity between the atoms. Eg. C5H12
H

CH3
H3C

CH3

CH2

CH3

CH3

CH3

1.3.

H3C

Tertiary alcohol

An alcohol where the carbon atom holding the -OH group is attached
directly to three alkyl groups.
CH3
HO

CH3

CH3

Question 2 (10 marks)

Draw the following structures (2 marks each)
2.1.

Wedge-dash of (S)-1-bromoethanol.
CH3

OH
Br

2.2.

Wedge-dash of (1R)-1-chloro-1,2-dimethylcyclohexane.
Cl
CH3

2.3.

Fischer projection of (2R, 3R)-2,3-diflorobutane.

CH3

F
CH3

2.4.

2-cyclohexene-1,4-diol.
OH

OH

2.5.

3-bromo-2, 5-dichloro-4-fluoro-2-methylheptane.
F

CH3

Cl

Br

Cl

Question 3 (10 marks)

Complete the following reactions. (2 marks each)
OCH3

Cl

NaOCH3

3.1.

note stereochemistry
2

NH2
Br

NH3

3.2.
OH

H2SO4

Heat

3.3.

OH
CH3

3.4.

NaIO4

OH

CH3

O
OH

PPC
CH2Cl2

3.5.

Question 4 (12 marks)

State whether the reaction is SN1, SN2, E1 or E2 and give product(s). (3
marks each)
-OC(CH3)3

CH3CH2CH2CH2Br

Heat

4.1.

H3CH2CHC

CH2

E2

OH

Br

OH0oC

4.2.

SN2
CH3

CH3

H2O
H3C

4.3.

Cl

H3C

C
CH3

CH3

OH

SN1

H3C

4.4.

CH3

OH

CH3

H
CH3

H2SO4

C
CH3

H3C

E1

Question 5 (20 marks)

5.1. Give the racemic products and mechanism for the following
reaction. Please take note of stereochemistry.
(6 marks)

CH3

H3CH2C
C

Cl

H 2O

Right hand attack

CH3

H3CH2C
C

Cl

H3CH2C

H3C

CH3
H3CH2C

C+

H2O+

H2O

-H+
H3C
H3CH2C

OH

Left hand attack:

CH3

H3CH2C
C

H3CH2C

Cl

CH2CH3

CH3
C+

OH2

CH3

H2O

-H+
CH2CH3
HO

CH3

5.2. Write a complete mechanism for the following SN2 reaction. What
will happen to the rate of reaction if we double the concentration of a
nucleophile?
(4 marks)

H
C
H3CH2C

CN-

Cl
CH3

H
H

CN

H3CH2C

Cl

NC
H3CH2C

CH3

Cl

NC

CH3

transition state

CH3
CH2CH3

The rate will also increase when we increase the concentration of nucleophile.

5.3. Give the mechanism and products for the following reactions:
H
H3C

(a).

OH

HBr

(5 marks)
5

Step 1: protonation of OH
Step 2: H2O+ leaves
Step 3: formation of carbocation
Step 4: carbocation is attacked by BrStep 5: formation of alkyl halide

H
H3C

(b).

OH

H2CrO4

(5

marks)