Chemistry of Functional Groups (CHMS2206)

BSc, Chemistry - CHMS

Semester: Second Semester

Level: 200

Year: 2019

Answers (200 )
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 ( 1.5 marks)
Compound A (C
4
H
6
) reacts with hydrogen and a platinum catalyst to yield butane. Compound A decolorizes
Br
2
in CC1
4
and aqueous KMnO
4
, but is does not react with Ag (NH
3
)
2
+
. On treatment with hydrogen and
Ni
2
B (P-2 catalyst). A is converted to B (C
4
H
8
). When B is treated with OsO
4
followed by treatment with
N
a
HSO
3
, B is converted to C (C
4
H
10
O
2
). Compound C cannot be resolved. Provide structures for A-C.
NB: Me
2
S can replace the mixture H
2
O/Zn in the ozonolysis reaction
Exercise 3(3.5 marks)
An alkane D with the formula C
6
H
14
reacts with chlorine to yield three compounds with formula C
6
H
13
Cl, E, F
and G. Of these, only F and G undergo dehydrohalogenation with sodium ethoxide in ethanol to produce an
alkene. Moreover, F and G yield the same alkene H (C
6
H
12
). Hydrogenation of H produces D. Treating H with
HCl produces a compound I that is an isomer of E, F and G. Treating I with Zn and acetic acid gives a
compound J that is isomeric with D. Propose structures for D-J.
Exercise 4 (4.5 marhs)
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 (5.5 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) czs-Oct-4-ene (d) trans Oct-4-ene (e) Octan-4-ol (f) meso-Octane-4,5-diol
Exercise 6 (4.5 marks)
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a)
- What is the physical aspect of the first four alkanes at room temperature? 0.5mark
b)
- Classify the following alkanes according to their increasing boiling points: 2-methylbutane, pentane,
2,2-dimclhylpropane. Justify your classification. 0.5x2mark
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.
d) Give the more modem statement of the Markovnikov’s rule
O.Smark
Exercise 7 (3.5 marks)
Write structure formulas for the following reactions. If more than one product is possible, tell which one
would be the major product
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