THE UNIVERSITY OF ZAMBIA

SCHOOL OF NATURAL SCIENCES

CHE 2105: Organic Chemistry for Medical Students
Tutorial Sheet 2
26th June, 2023

For the week beginning 26th June, 2023

Note: Tutorial mini-tests/quizzes shall be given during the first 15 minutes of each tutorial
session

QUESTION ONE
(a) From the given pairs of molecules given below, choose which one is a stronger nucleophile:
-
(i) NH3 and NH2
- H2O
(ii) OH and
- -
(iii) HS and CN

(b) What product would be formed from the SN2 reaction of the following?
(i) 2-bromobutane and hydroxide ion
(ii) (R)-2-bromobutane and hydroxide ion

(c) Arrange the following alkyl bromides in order of decreasing reactivity in an SN2 reaction:

1-bromo-2-methylbutane, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, and

1-bromopentane.

(d) When methyl bromine is reacted with sodium hydroxide, methanol is produced.
(i) Name and write a detailed reaction mechanism of this reaction
(ii) Give the rate law for this reaction and state the overall order of this reaction
(iii)What happens to the rate when the concentration of the nucleophile is doubled?
(iv) What happens to the rate when the concentration of the nucleophile and substrate are
doubled?

QUESTION TWO

(a) Indicate the effect on the rate of SN1 and SN2 reactions of the following:

(i) Doubling the concentration of substrate (RL) or Nu-

(ii) Using a mixture of ethanol and H2O or only acetone
(iii) Increasing the number of R groups on the C bonded to the leaving group, L
(iv) Using a strong :Nu-
 (b) List the following alkyl bromides in order of decreasing reactivity in the indicated reactions:

Br

Br Br
(I) (II) (III)
(i) SN1 reactivity.
(ii) SN2 reactivity.

(c) Benzyl chloride readily under goes SN1 reactions with water to form benzyl alcohol. Write a
detailed mechanism for this reaction show all resonance structures involved in the stabilization
of the carbocation.
(d) Account for the following observations when (S)-CH3CH2CH2CHID is heated in acetone
solution with NaI.
(i) The enantiomer is racemized
(ii) if radioactive *I- is present in excess, rate of racemization is twice the rate at which the
radioactive *I- is incorporated into the compound.

QUESTION THREE

(a) Which product or products would you expect to obtain form each of the following reactions. In
each part give the mechanism (SN1, SN2, E1, or E2) by which each is formed and predict the
relative amount of each product, say whether; it is the only product, major or minor, etc.
Br EtO-
(i)
EtOH, 50 oC

t-BuO-K+
(ii) Br
t-BuOH, 50 oC

t-BuO-K+
(iii)
Br
t-BuOH, 50 oC

Cl
(iv) MeO-Na+
MeOH, 50 oC

MeO-Na+
(v)
Br MeOH, 50 oC
(b) Provide the starting materials for the preparation of the following compounds via SN2
reactions:
(i) CN

(ii) N CH3I

(iii) N3

(c) Suggest a most likely mechanism to account for the product of the following reaction.

D
H3PO4
D

OH

(d) Your task is to prepare styrene by the following methods; which one would you choose
to give the best yield of styrene?
Br
Br
(1) KOH (2) KOH
EtOH, heat EtOH, heat