W1-2-60-1-6

JOMO KENYATTA UNIVERSITY

OF AGRICULTURE AND TECHNOLOGY

University Examinations 2012/2013

YEAR I SEMESTER II EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE

IN FOOD SCIENCE AND TECHNOLOGY/ FOOD SCIENCE AND NUTRITION/ HUMAN
NUTRITION AND DIETETICS/ FOOD SERVICE AND HOSPITAL MANAGEMENT/
BIOMECHANICAL AND PROCESSING ENGINEERING/ SOIL, WATER &
ENVIRONMENTAL ENGINEERING/ AGRICULTURAL ENGINEERING

SCH 2108: ORGANIC CHEMISTRY

DATE: AUGUST 2012 TIME: 2 HOURS

INSTRUCTIONS: ANSWER QUESTION ONE (COMPULSORY) AND ANY OTHER TWO QUESTIONS

USEFUL DATA: ATOMIC NUMBERS: H = 1; C = 6; O =8; N =7; F= 9; Br = 35; I = 53; Cl = 17

QUESTION 1

a) Draw all the constitutional isomers of C4H10O and give their systematic
(IUPAC) name. (5 marks)

b) Which of the following carbocations is more stable than the other? Explain.

CH2CH3
1. b. CH3CH2CCH3 CH3CH2CHCH2CH3
(2 marks)

c) Give the systematic (IUPAC) names of each of the following compounds:-

 CH3CH3
1.c.
Cl
i. CH3C CHCH3 iii.
ii. CH3CHCHCH3 CH3
CH3
Br
OH CH2CH3
iv. CH3CH2CH2CHCH2CHCH3
NO2
CH3
v.

vi.CH3CH2CH2CHCOOH
CH2CH3 NO2

vii. O
viii.

CH3

ix. CH3CH2CHCHO x. CH3CH2COOCH2CH3

CH3

(10 marks)

d) Explain the following terms concisely:

i) Homologons series

ii) Functional group

iii) Enactiomers

iv) Dehydration reaction (4 marks)

e) Predict the major product in each of the following reactions:

 Ni
1. e. i. CH3CH2CH2CH=CH2 H2 ?

ii. CH3CH2CH=CCH3 HBr ?

CH3
iii. CH3CH=CHCH2CH3 Br2 ?
CH2Cl2

iv. CH2
HCl ?

v. CH3CH=CH2 H2O2 ?
CH3 BH -
3 OH

f) Complete the following reactions. (5 marks)

f.i. CH3CH2C CH3 NaBH4

?
O
CHO
ii.
1. Ag2O, NH3
? ?
H3O

H3O
iii. CH3CH2CHO CH3CH2CH2MgBr ?
(4 marks)

QUESTION 2

a) Show the asymmetric carbon in each of the following compounds using

an asterick.

OH CH3
Q2 a .i. CH3CH2CHCH3 ii. CH3CCH2CH3 iii.
Cl Br
CH2CH3
Br
iv. CH3CH2CHCH3 v. CH3CH2CCH3 v. CH2=CHCHCH3
CH2CH3 CH2CH2CH3 NH2
(6 marks)

b) Predict the major products in each of the following reactions:

 Q2 b.i. Saretts -Collins ?
CH3CH2CH2OH
reagent

1. LiAlH4/Ether ?
ii. CH3CH2CH2CHO
2. H2O

iii. CH3CH2CHOH HCl/ZnCl2 ?

CH2CH3 heat

iv. CH3CH2CHCH3 KMnO4/H2SO4 ?

80 0 C
OH
CH3MgBr/Ether
v. CH3C N ?
H2O

vi. CH3CH2OH PCC

O ?
25 C

(6 marks)

c) Briefly explain the following observations:

i) Aldehydes and ketones have higher boiling points than hydrocarbons

of similar chain lengths.

ii) Propan – 1 – ol is soluble in water while propane is not. (4 marks)

d) State four types of reactions that alcohols undergo. (4 marks)

QUESTION 3

a) Write a suitable reaction mechanism for the following reaction:

CH3 CH3
Q3 a. CH3 C Br H2O CH3 C OH HBr
CH3 CH3
(6 marks)

b) Draw the perspective formulae for the following:

i) S – 2 – bromobutane

ii) R – 1 – bromopentan – 2 – ol

iii) S – 2 – methyl – 1- butanol

iv) R – 1, 2 – dichlorobutane
 (Show how you arrived at each formula) (8 marks)

c) Complete the following reactions:

c.
FeCl3
i. Cl2 ? ?

ii.
H2SO4 ? ?

iii. O
1. AlCl3
CH3CH2CCl ? ?
2. H2O
(6 marks)

QUESTION 4

a) Show the initiation, propagation and termination steps for the

monobrominatic of ethane. (6 marks)

b) Suggest a suitable reaction mechanism for the nitration of benzene:

NO2
Q4 b. Conc H2SO4
Conc HNO3 H2O

(5 marks)

c) Draw and label the E and Z isomers of the following compounds:

c. i. CFCl=CIBr ii. CH3CH2CH=CHCH3

iii.CH3CH2C=CHCHCH3
CH3 CH3
(Show your working to arrive at the answer) (6 marks)

d) Describe simple chemical tests that would distinguish between:

i) An alkene and an alkane

ii) A ketone and an aldehyde

iii) An alcohol and a carboxylic acid (3 marks)