THE UNIVERSITY OF TRINIDAD & TOBAGO

ALTERNATE FINAL ASSESSMENT/EXAMINATIONS APRIL/MAY 2014

Course Code and Title: LFSC1002 – LIFE SCIENCES

Programme: BASc. [Common Yr I]

Date and Time: TBD Duration: 3 hours

PLEASE READ ALL INSTRUCTIONS CAREFULLY BEFORE YOU BEGIN THIS

EXAMINATION

Instructions to Candidates

1. This paper has 6 pages and 5 questions.

2. You are required to answer ALL questions in your answer booklet
3. You are required to return the question paper along with your answer booklet.

Key Examination Protocol

1. Students please note that academic dishonesty (or cheating) includes but is not limited to
plagiarism, collusion, falsification, replication, taking unauthorized notes or devices into an
examination, obtaining an unauthorized copy of the examination paper, communicating or
trying to communicate with another candidate during the examination, and being a party to
impersonation in relation to an examination.
2. The above mentioned and any other actions which compromise the integrity of the academic
evaluation process will be fully investigated and addressed in accordance with UTT’s
academic regulations.
3. Please be reminded that speaking without the Invigilator’s permission is NOT allowed.

© The University of Trinidad & Tobago

April/May 2014 Alternate Final Examinations
(LFSC1002)
Page 1 of 6
1) a. Draw the “stick formula” of the following compound: [4 mks]

H H
H C H H

C C C C

H H H
C C
C
H
H
H C
H
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 2-
methylbutane 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) Using curved arrows, describe the mechanism by which 2-methylbut-2-ene reacts
with HBr to form Product I. [5 mks]
(ii) Explain why Product I is formed in much larger proportions compared with Product
II, and state the specific Rule that is being observed here. [3 mks]
(iii) If peroxides were utilized in the reaction between 2-methylbut-2-ene and HBr, draw
the structure of the major product formed in this case. [2 mks]

© The University of Trinidad & Tobago

April/May 2014 Alternate Final Examinations
(LFSC1002)
Page 2 of 6
2) a) Give the IUPAC names of the Compounds IV, V & VI shown below: [6 mks]

OH

H H OH H
CH 2CH3

H C C C C H

H H CH 3 H COOH

Compound IV Compound V Compound VI

b) (i) Define the terms “structural isomerism” and “geometrical isomerism” [4 mks]

(ii) Draw the structural formulae of SIX isomers of Compound VII shown below: [6 mks]

H H H

H C C C C H

CH 3 H H

Compound VII

c) Identify which of the following compounds are electrophiles and which are nucleophiles:
[4 mks]

O R R
R
Br Br C C N C C

R R
R (iii)
(i)
(ii) (iv)

© The University of Trinidad & Tobago

April/May 2014 Alternate Final Examinations
(LFSC1002)
Page 3 of 6
3) a) Give the IUPAC name of Compound Y shown below: [3 mks]

CH3

N Compound Y
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
O C H
N Tyrosine
HO H
H

c) Draw the structural formula of 2-methyl-3-pentanamine [3 mks]

d) The structure of Dopamine is shown below.

HO CH 2 CH 2 NH 2

Dopamine

HO

Do you expect dopamine to be more or less basic than tyrosine? [3 mks]

e) In general, which are more basic – amines or amides? Explain your answer. [2 mks]

f) Between ethylamine and ethanamide, which is more polar? [2 mks]

© The University of Trinidad & Tobago

April/May 2014 Alternate Final Examinations
(LFSC1002)
Page 4 of 6
g) (i) Complete the following neutralization reaction: [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) a) 2-bromobutane reacts with highly concentrated CH 3 CH 2 O-Na+ (a large base) to produce

two products, Z & L. In this product mixture, the ratio between Z & L is 1:4. Compound L
exhibits cis/trans isomerism whilst compound Z does not.

(i) What is the name of the type of reaction occurring in (a) above? [2 mks]

(ii) Draw the structures of compounds Z and L. [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]

© The University of Trinidad & Tobago

April/May 2014 Alternate Final Examinations
(LFSC1002)
Page 5 of 6
5) a) Compound X shown below can be synthesized using a Grignard reagent and a carbonyl
compound.
H OH

C C H

H H

Compound X

(i) What class of alcohols does compound X belong to? [1 mk]

(ii) Write the reaction to show the formation of the Grignard reagent which must be used in the
synthesis of this alcohol. [3 mks]
(iii) What is the identity of the carbonyl compound which must be used in the synthesis of this
alcohol? Draw its structure [2 mks]
(iv) Draw the reaction mechanism between the carbonyl compound and the Grignard reagent to
form compound X. [4 mks]

b) (i) Write the formula of “sodium borohydride” [1 mk]

(ii) What anion does this sodium borohydride generate in solution? [1 mk]

c) The reaction between compound XI shown below and sodium borohydride results in
Compound XII.

O
Sodium borohydride
C
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**************************

© The University of Trinidad & Tobago

April/May 2014 Alternate Final Examinations
(LFSC1002)
Page 6 of 6