ORGANIC CHEMISTRY 2 (CHM 201M/MCHA 021) TUTORIAL TEST 1 15

FEBRUARY, 2019

SECTION A [25]

USE THE ANSWER SHEET PROVIDED TO ANSWER ALL THE QUESTIONS.

1. What kind of reaction does the conversion of A to B represent?

2. Which of the following compounds contain tertiary (3°) radical carbons?

3. Which of the following structures has a different configuration from the other
three?

4. Which of the following compounds is conjugated?

(5) Regioselective reaction involving a cylic alkene (3)

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ORGANIC CHEMISTRY 2 (CHM 201M/MCHA 021) TUTORIAL TEST 1 15
FEBRUARY, 2019

SECTION B [75 Marks]

QUESTION 1 [20 Marks]

(a) Give an example of an alkene which does not show cis-trans isomerism.
(2)

(b) Give an example of a polymerization reaction of styrene when benzoyl

peroxide is used as an initiator. Use at least three monomers. (3)

(c) An example of a Homolytic bond cleavage

(d) An example of a carbocation that is stabilized by a heteroatom; show at least

one resonance structure of the carbocation.

(e) (3)

+ heat

(f) Draw all the possible resonance structures of the following compound (4)

(g) Draw a stepwise mechanism for the following reaction. (4)

hv
+ Br
NBS
Br

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ORGANIC CHEMISTRY 2 (CHM 201M/MCHA 021) TUTORIAL TEST 1 15
FEBRUARY, 2019

(h) Consider the reaction below to answer the following questions: [7]

HBr (1 eq) +
A B

(i) The nucleophile in the reaction is (draw the structure) ……………… (1)

(ii) The electrophile in the reaction is(draw the structure) ……………… (1)

(ii) Draw the structure of product A and B. (4)

(iv) Which product is kinetically controlled? (1)

(i) Write a stepwise mechanism that accounts for the formation of product A and
B. Show all intermediate structures and electron flow with arrows. Indicate the
percentage yield of each product. (4)

HBr (1eq)
A + B
80oC