Chemistry of Functional Groups (CHMS2206)
BSc, Biochemistry - BCHS
Semester: Second Semester
Level: 200
Year: 2017
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REPUBLIC OF CAMEROON REPUBLIQUE DU CAMEROUN
Peace-Work-Fatherland Paix-Travail-Patrie
THE UNIVERSITY OF BAMENDA
UNIVERSITE DE BAMENDA
P.O. Box 39 Bambili
Faculty of Science (Department of Chemistry Lecturer. Dr BANKEV
Course Code: CHMS 2206 Course Title: Chemistry of Functional groups
Date: 14/07/2017 Hall: mj408 Time: Ilh30-13h30 (3 hours)
Instructions: Please answer all questions
Exercise 1(04 marks)
a) - Give the reasons why alkanes and cycloalkanes are almost totally insoluble in water? 0.5mark
b) - Establish the difference between homolytic cleavage and heterolytic cleavage. 0.5mark
c) - Give the reason why alkanes are not involved in addition reactions. 0.5mark
d) - How many steps are involved in this chlorination reaction? Give those steps and tell what consist of any of
them. 0.5x4marks
e) - Give the more modern statement of the Markovnikov’s rule O.5mark
Exercise 2(03 marks)
Reaction of 3,3-dimethylbut-l-ene with hydrogen iodide yields two compounds A and B, each having the molecular
formula C
6
H
13
I, in the ratio A:B = 90:10. Compound A, on being heated with potassium hydroxide in n-propyl
alcohol, gives only 3.3-dimethylbut-l-ene. Compound B undergoes elimination under these conditions to give
2,3-dimethylbut~2-ene as the major product. Suggest structures for compounds A and B, and write a reasonable
mechanism for the formation of each.
Exercise 3 (3.75 marks)
Give the structural formulae for the alkenes formed on dehydrobromination of the following alkyl bromides and
underline the principal product in each reaction: (a) 1-bromobutane, (b) 2-bromo butane, (c) 3-bromopentane, (d)
2-bromo-2-methylpentanc, (e) 3-bromo-2-methylpentane, (f) 3-bromo-2,3-dimethyl-pentane.
Exercise 4 (2.25 marks)
Draw the structural formula of the alkene that reacts with ozone followed by dimethyl sulfide to give each product or
set of products.
Exercise 5 (5.5 marks)
a) - Show how to convert acetylene and 1-bromoethane into but-l-ene. All of the carbon atoms of the target molecule
must be derived from the given starting materials.
b) - Propose a synthesis of each compound starting from acetylene and any necessary organic and inorganic
reagents.
(a) Oct-4-yne (b) Octan-4-one (c) ds-Oct-4-ene (d) trans-4-Octene (e) 4-Octanol (f) meso-Octane-4,5-diol
Exercise 6 (1.5 marks)
There are three constitutional isomers with the molecular formula C
5
H
12
. When treated with chlorine at 300°C, isomer
A gives a mixture of four mono chlorination products. Under the same conditions, isomer B gives a mixture of three
monochlorination products, and isomer C gives only one monochlorination product. From this information, assign
structural formulas to isomers A, B, and C.
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Exercise 7 (2 marks)
(a) How many stereoisomers are possible for 4-methylcyclohexane-l,2-diol?
(b) Which of the possible stereoisomers are formed by oxidation of (S)-4-methylcyclohexene with osmium
tetroxide?
(c) Is the product formed in part (b) optically active or optically inactive?
Exercise 8 (2.5 marks)
Show how to convert cyclohexanol into racemic trans-cyclohexane-l,2-diol. Show all required reagents and all
molecules synthesized along the way.
Cyclohexanol Trans-cyclohexane-1,2-diol
(racemic)
Exercise 9 (3 marks)
Show how to convert (E)-hex-3-ene into propyl propionate. You must use (E)-hex-3-ene as the source of all carbon
atoms in the target molecule. Show all reagents and all molecules synthesized along the way.
Exercise 10 (2.5 marks)
Using 1-bromobiitane and any necessary organic or inorganic reagents, suggest efficient syntheses of each of the
following alcohols:
a) - Pentan-1 -ol 0.5mark
b) - Hexan-2-ol 0.5mark
c) - 1-Phenylpentan-1-ol 0.5mark
d) - 3-Methylheptan-3-ol 0.5mark
e) - Butylevelobutan-1 -ol 0.5mark
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