Organic Chemistry For Mls Question Paper

Organic Chemistry For Mls

Course:Bachelor Of Science

Institution: Kenyatta University question papers

Exam Year:2009

KENYATTA UNIVERSITY
UNIVERSITY EXAMINATIONS 2009/2010
FIRST SEMESTER EXAMINATION FOR THE DEGREE OF BACHELOR OF
SCIENCE

HML 110: ORGANIC CHEMISTRY FOR MLS

DATE: Tuesday
29th December 2009

TIME: 2.00pm -4.00pm

INSTRUCTIONS:
Answer all Questions

Q1. (a)
You are provided with the following structure of an organic compound 1.

OH
a
f
d
b
O
1

(i)
Draw and label all the functional groups in compound 1.
(2 mks)
(ii)
Indicate type of hybridization for carbon atoms labeled b and f. (2 mks)
(iii)
Which of the labeled carbon atoms would you classify as tertiary and
quaternary?

(2 mks)

(b)
Provide systematic (IUPAC) names for the following compounds,
indicating
stereochemistry
where appropriate.

(6 mks)
Page 1 of 4

CH3 CH3
F
Cl
Cl
(i)
(ii)
(iii)
OH
(v)
(iv) Br
CH2CH3

Br

(c)
Draw the structure of each of the following compounds including the
stereochemistry
where
appropriate.
(6
mks)
i.
5-Bromo-2-methyl –3-heptyne
ii.
5-chloro-1-methyl-5-(isopropyl)cyclohex-1-ene
iii.
trans-2-bromocyclobutanol
iv.
(E)-2-methyl-1,5-octadiene

Q2. (a)
Quantitative analysis of quinone showed the presence of carbon,

hydrogen, and oxygen. Combustion of 0.105 g of the quinine gave 0.257 g
of
CO2 and 0.035 g of H2O. If the molecular mass of the quinone is 108g.
Calculate
i.
Empirical formula of the quinone
ii.
Molecular formula of the quinone

[C = 12.01, H = 1.00, O = 15.99]

(7 mks)

(b)
Draw the structural formulas and give names of any three isomeric

compounds with the molecular formula C3H6O. (6
mks)

(c)
Monobromination of methylcyclopropane (2) with molecular bromine in

presence of light gives three brominated products, with one predominating
over
the
others.

Page 2 of 4

CH3
2

i.
Draw possible monobrominated isomers of the reaction. (3 mks)
ii.
Which of the compound in (i) above would predominate over the
others?

(1mk)

Q3.
(a)
Provide the structure(s) of the major organic compounds that are expected

in the following reactions. Indicate the stereochemistry where necessary.

(16 mks)

Na, heat
2CH
i)
3CH2CH2Br
A
Na / Liq NH
ii)
3
CH3C CCH2CH3
B
1. B2H6, ether
iii
C
2. H2O2, OH-
1. O3
iv)
D
2. Zn, OH-, Heat

1. NaNH
(v)
2
E
2.CH3CH2Br
1. OsO4
(vi)
F
2. Aq. NaHSO3
H
(vii)
CH
2, Lindlars Catalyst
3
C CCH2CH3
G
viii)
Br
H2O
H

(b)
Determine the formal charge for each atom and the ionic charge for the following.

[N = 5, O = 6]

(4 mks)
O N O
O

Page 3 of 4

Q4.
(a)
Using curly arrows show the movement of electrons in the following

reactions.

CH3
(i)
H+
H3C C CH +
2
H2O
H3C C OH
CH3
CH3
Br
Br
(ii)
2, CCl4
in dark
Br
10 mks

(b)
Give a simple visual chemical test you would perform to differentiate

between the pairs of the compound below. Explain what happens in each

case.

(5 mks)
(i)
and
OH
OH
(ii)
and

Page 4 of 4

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