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The University of Trinidad & Tobago: Alternate Final Assessment/Examinations April/May 2014
The University of Trinidad & Tobago: Alternate Final Assessment/Examinations April/May 2014
The University of Trinidad & Tobago: Alternate Final Assessment/Examinations April/May 2014
ALL
Duration: 3 hours
INSTRUCTIONS
CAREFULLY
BEFORE
YOU
BEGIN
THIS
Instructions to Candidates
C
C
C
H
H
C
H
H
C
[4 mks]
H
H
b) In a laboratory, a student was given two test tubes one contained 2-methylbutane and
another contained 2-methylbut-2-ene, but it was not known which tube contained which
compound.
(i) Draw the structural formulae of 2-methylbutane and 2-methylbut-2-ene.
[2 mks]
(ii) Describe a simple laboratory test the student could use to distinguish between 2methylbutane and 2-methylbut-2-ene, and hence identify which test tube contained which
compound. Include relevant equations in your answer and any observations seen.
[4 mks]
(c) When 2-methylbut-2-ene reactions with hydrogen bromide, two products are obtained,
Product I & Product II. Product I is produced in a much larger amount (major product) compared
with Product II (minor product).
(i)
(ii)
(iii)
2) a) Give the IUPAC names of the Compounds IV, V & VI shown below:
[6 mks]
OH
OH
CH 3
CH 2CH3
H
COOH
Compound IV
Compound VI
Compound V
[4 mks]
(ii) Draw the structural formulae of SIX isomers of Compound VII shown below: [6 mks]
H
H
CH 3
Compound VII
c) Identify which of the following compounds are electrophiles and which are nucleophiles:
[4 mks]
Br
Br
(i)
(ii)
(iii)
R
C
(iv)
[3 mks]
CH3
Compound Y
N
H3 C
b) The amino-acid Tyrosine is shown below. Copy this structure in your answer booklet and
circle and name the functional groups found in tyrosine.
[3 mks]
OH
H
H
C
C
H
Tyrosine
N
HO
H
H
[3 mks]
CH 2
CH 2
NH 2
Dopamine
HO
[3 mks]
e) In general, which are more basic amines or amides? Explain your answer.
[2 mks]
[2 mks]
[2 mks]
HCl
N
H 3C
CH3
(ii) Do you expect the product of the neutralization reaction in (i) above to be ionic or covalent in
nature?
[2 mks]
[4 mks]
(iii) Show the mechanism of the reaction which produces Z and that which produces L.
[6 mks]
(iv) What is the name of the rule being observed which allows for the formation of a major
product (compound L) and a minor product (compound Z). [2 mks]
(v) Draw the structures and give the IUPAC names of the two isomers of compound L.
[6 mks]
5) a) Compound X shown below can be synthesized using a Grignard reagent and a carbonyl
compound.
H
OH
Compound X
[1 mk]
c) The reaction between compound XI shown below and sodium borohydride results in
Compound XII.
O
Sodium borohydride
Compound XII
CH 3
Compond XI
(i) What type of reaction is occurring during the conversion of Compound XI to Compound XII?
[1 mks]
(ii) Draw the structural formula of Compound XII
[3 mks]
(iii) Using curved arrows, show the mechanism of the reaction which converts compound XI into
compound XII in the presence of sodium borohydride.
[4 mks]
******************************END OF EXAMINATION**************************