Chemistry of Functional Groups (CHMS2206)
BSc, Chemistry - CHMS
Semester: Second Semester
Level: 200
Year: 2019
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: Anagho/Nono
Course code: CHMS2206 Course title: Chemistry of functional groups
Date: 09/07/2019 hall: PBA07 & PBA08 time: 15:00-17:00 (2 hours)
Instructions: Please answer all questions.
Exercise 1 (07 marks)
What will be the major product of the reaction of 1-methylcyclohexene with each of the following reagents?
a) -HCl+peroxide
b) -Br
2
/CH
3
OH
c) -O
3
d) - Product of c)- and H
2
O
e) - Product of c)- and H
2
O/Zn
f) - Br
2
, CCl
4
g) - Perbenzoic acid then H
3
O+, H
2
O
h)- Hg(OAc)
2
, THF-H
2
O then NaBH
4
, OH
-
i) - BH
3
/THF followed by H
2
O
2
/HO
-
j) – CH
3
OH/H
+
k) - ICl
l) - Hg(O
2
CCF
3
)
2
+CH
3
OH followed by NaBH
4
m) - OsO
4
then NaHSO
3
n) - KMnO
4
, OH
-
, heat, then H
+
Exercise 2 (5 marks)
Predict the major organic product of each of the following reactions
a)-
Exercise 3 (3.5 marks)
An alkane K with the formula C
6
H
14
reacts with chlorine to yield three compounds with formula C
6
H
13
Cl, L, M and
N. Of these, only M and N undergo dehydrohalogenation with sodium ethoxide in ethanol to produce an alkene.
Moreover, M and N yield the same alkene O (C
6
H
12
). Hydrogenation of O produces K. Treating O with HCl
produces a compound P that is an isomer of L, M and N. Treating P with Zn and acetic acid gives a compound Q
that is isomeric with K. Propose structures for K-Q.
Exercise 4 (4.5 marks)
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Show how Grignard reactions could be used to synthesize each of the following compounds.
a) tert-Butyl alcohol; b)- pentan-2-ol; c)- 2-phenylbutan-2-ol; d)- hexan-l-ol; e)- 2-phenylethanol; f)- 3-
methylpentan-3-ol
Exercise 5 ( 5 marks)
Compound R decolorizes Bn in CCl
4
and aqueous KMnO
4
, it also reacts with Ag (NH
3
)2
+
to yield a precipitate. R reacts in turn with
sodium amide (NaNH
2
) to yield S. S reacts with 1-bromoethane to yield T. T is treated with sodium in liquid ammonia to yield but-l-ene.
T in addition also reacts with sodium amide to yield U. U reacts with I-bromoethane to yield V. V is treated with aqueous sulfuric acid
containing mercury (II) sulfate to yield W V, when treated with lithium in liquid ammonia gives X, but when treated P-2 catalyst, it
yields Y. When X or Y is treated with acidified water the same product Z is obtained. When X or Y is treated with OsO
4
followed by
treatment with N
a
HSO
4
they are converted to the same compound AB. Propose structures and systematic names for R-Z and AB.
Exercise 6 ( 5.25 marks)
a) Define the following: electronegativity, homolytic cleavage.
b) - What is the impact of inductive effect on acidity of compounds.
c) - Give the different systems that involve resonance.
- What is the difference between the Markovnikov’s and the Kharasch’s rules
Which of the hydrogen halides follows the Kharasch’s rule. Specify the conditions under which the Kharasch’s rule is applied and give
the reason of the peculiar situation
What reason makes organic halides to be highly reactive class of molecules?
Exercise 7 (5 marks
Write chemical equations, showing all necessary reagents, for the preparation of pentan-l-ol by each of the following methods:
a)
- Hydroboration—oxidation of an alkene lmark
b)
- Use of a Grignard reagent lmark
c)
- Reduction of a carboxylic acid lmark
- Reduction of a pentyl ester
Reduction with sodium hornhydride
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