CHM456 TUTORIAL2 MAY2012

CHAPTER4,5AND6

QUESTION 1

Give the IUPAC names for the following compounds.
Cl
Br
F
a)
b) c)
d) e)
f)

QUESTION 2

Consider the 3 different butane conformations as shown below

a) Name each of the butane conformation (I-III).

b) Arrange the stability of the conformation in increasing order. Explain your answer.

QUESTION 3

Consider the following reaction scheme.

CHM456 TUTORIAL2 MAY2012
CHAPTER4,5AND6

a) Give

i) the reagents of P, Q, R and U.
ii) the structure of the products of S and T.

b) Name the rule which dictates the product of S.


QUESTION 4

Classify the mechanism of each of the following reactions as SN1, SN2, E1 or E2.

QUESTION 5

Propose a mechanism leading to the following products.

CHM456 TUTORIAL2 MAY2012

CHAPTER4,5AND6

QUESTION

a) Using examples, state the differences between E1 and E2 elimination reactions.

b) Explain the formation of approximately 50% inverted and 50% racemic products from an
SN1 reaction.

QUESTION 5

a) Write the mechanisms for the following conversions.

QUESTION 6
Each of the following alcohols, Y and Z, has been subjected to acid catalyzed dehydration
and yields a mixture of two isomeric alkenes. Draw the isomers of the alkenes in each case,
and determine which one is the major product.

QUESTION 7
(S)-3-bromo-3-methylhexane is reacted with a strong nucleophile of thiol (SH) to give W
as the product via SN2 reaction as shown below.

i) Determine whether the starting material of (S)-3-bromo-3-methylhexane is optically
active or not.
ii) Give the structure of the product, W.
iii) Suggest the absolute configuration of W.
iv) If the nucleophile of SH" is changed to a weaker nucleophile of H2O, give the
structure of the new product and its stereochemistry. Explain your answer.