Professional Documents
Culture Documents
OF BOTSWANA EXAMINATIONS
2003-2004 SEMESTER
FRONT PAGE
DURATION
2 HOURS
DATE: 2/12/2003
ORGANIC
CHEMISTRY
SUBJECT
CHEMISTRY
QUESTIONS
TO USE MOLECULAR
ID
GROUP NO
MC
TOTAL
YOU ARE
of pages is 16 including
Number
2
SECTION all questions A (2 marks each)
Answer 1
The term tautomerism refers to: (a) Reaction of amines with aldehydes and ketones (b) Reaction of enolates with aldehydes and ketones (c) An equilibrium between a ketone or aldehyde and its enol form (d) Formation of acetals from aldehydes
2. Cyclohexanone is the product when cyclohexene is (a) treated with acidic water followed by FCC (b) ozonolysed (c) treated with a Grignard reagent followed with acidic work-up (d) treated with sodium borohydride
b)
c)
d)
d
set of groups
Monohalogenation of propane in the presence of a halogen and light gives two chloro products. The two products are obtained in the (a) propagation step (b) initiation step (c) termination step (d) both the termination and propagation steps
5 Indicate
(a) (b) (c) (d)
the correct priority order for the given -NHCH3> -OH> -OCH3> -CH2NH2 -OH> -OCH3> -NHCH3> -CH2NH2 -OCH3> -OH> -NHCH3> -CH2NH2 -CH2NH2> -NHCH3> -OH> -OCH3
6. The order
of reactivity
of alkyl
halides
in an SN
mechanism
is:
product
reaction?
a)
/Jl"""",~
OH
0H
b)
/)""';~/
0H
0
c)
..-",u.,.../, H0 C
OH
d)
"""'~'""CO2H
as:
N H
A mixture of benzene, propene and sulphuric acid reveals a number of facts. Which of the facts given below are true? (a) is an addition reaction, (b) an electrophilic substitution (c) it gives two products (d) all the above are true
IO.Treatment
of
ethene
oxide acid
with
sodium
methoxide
in
methanol
followed
(a) (b) (c) (d)
Reduction
an an an an
of an amide with
lithium
aluminium
hydride
results
into
12.In organic reactions, protonation (a) slow and irreversible (b) slow and reversible (c) fast and reversible (d) fast and irreversible
3.The reaction of a Grignard reagent with a ketone followed by an acidic work-up yields (a) a product oxidisable with Jones reagent (b) a product that readily gives a carbocation in acidic media (c) a product impossible to undergo simple oxidation with Jones reagent (d) both (b) and (c)
4.Indicate the FALSE statement among the following: (a) Alcohols have higher boiling points than hydrocarbons of sim i jar molecular weight. (b) The conjugate base of an alcohol is an alkoxide
ethers
and
(c) Alcohols are more acidic than phenols (d) Low molecular weight alcohols are soluble in water
5 5. The reagent required for the self-condensation butenal is (a) sodium methoxide (b) hydrochloric acid (c) Tollen's reagent (d) pyridinium chlorochromate of ethanal to 2-
16.Ethanoyl chloride (a) reaction of (b) reaction of (c) reaction of (d) reaction of
can be prepared by: ethanoic acid with HCI ethanoic acid with methyl ethanoic acid with thionyl methanoic acid with ethyl
I8.Acid anhydrides are: (a) less reactive than esters towards nucleophiles (b) as good acids as carboxylic acids (c) prepared from reaction of acid chlorides and carboxylate salts or carboxyl ic acids (d) hydrolysed by water to give amides
19.The correct name for 2-ethyl-l-propanol (a) 2-sec-butylmethanol (b) I-pentanol (c) 2-hydroxymethylbutane (d) 2-methyl-l-butanol
is
20.The
with
major
sulphuric
product
acid is
in the dehydration
of
I-methylcyclopentanol
6 SECTION B
ii
2,2-Dibromohexanal
iii.
p-Bromophenyl
methyl
ether
IV
Propylene oxide
v. (R)-3-Methyl-l-hexyne
compounds.
(2 marks
each)
(i)
(ii)
//""\.j/"'-"".:===
(v)
Question
80%
]00% (i) What mechanism does each reaction follow and what are the competing mechanisms if any for each reaction?
(ii)
(iii)
and why?
(iv)
play?
9 (b) 3-Buten-2-o1 reacts with HBr to give a mixture (i) Write a mechanism for this reaction. of products (5 marks)
(ii)
Consider the stereochemistry of each product With this in mind, draw and name each product.
(7 marks)
above.
10
Question
Three
reactions
(2 marks each)
~A
HCN KOH
0
ii)
-)
1.
N +a C=CH
~
2. H30
0
iii)
1. NaBH4
~
0'"
0
2. H30
J
/
excess CH30H
H+
iv)
v)
Ag20
(b) Write equations for the synthesis of methyl propyl ether using the Williamson method. Consider all possibilities.
(4 marks)
(c)Arrange the following compounds in order of increasing acidity and briefly state reasons for your order: Trifluoroethanoic acid, ethanoic acid, ethanol, 2,2dichloroethanol
(6 marks)
12
Question Four
(a)
Provide the missing for reaction + products (ii i).
(14 marks)
in
the
following
reactions,
showing
mechanism
stereochemistry
where
necessary.
Provide
(i)
I-bromobutane
potassium
(-butoxide
in (-butanol
cis-I-bromo-4-methylcyclohexane solvent
NaCN
in an aprotic
(R)-3-bromo-3-methylhexane
+ aqueous acetone
13
(b) Which
will be more stable, cis- or trans-l,4-di-tertbutylcyclohexane? Explain your answer by drawing chair conformations for each isomer.
(6 marks)
14
Question Five
(a) Write a mechanism for the nitration of benzene in a mixture of sulphuric acid and nitric acid.
(6 marks)
(b)How does one convert the product above to aniline? Write an equation.
(2 marks)
15 (c) Show how the following compounds may be made from the given starting material. (i) Butanal as the only product from an alkene
(3 marks)
2-butanone
from ethyne
and alkyl
hal ide
(4 marks)
END OF EXAMINA
TION