SIC 2002 Assignment 2020/21(S1)

Name : Muhamad Nabil Najmuddin Bin Azman No. Matriks : 17188965/2 [ IIV180031 ]

1. Consider the following structures.

OH O O O
O OCH3 N
H OH

A B C D

a) Which compounds cannot easily be oxidized? Explain.

Generally, compound D cannot easily be oxidized because it is basically aromatic

and aromatic rings are resistant to oxidation.In addition, the second side chain group
on this compound are also readily oxidized.

b) Provide the structures of the common oxidation products for the compounds not listed
under (a).
SIC 2002 Assignment 2020/21(S1)

c) Determine the oxidation numbers for all carbon atoms connected to oxygen in B.

(10 marks)
SIC 2002 Assignment 2020/21(S1)

2. Consider the following reaction.

OCH3
Br Zn
E
F

a) Draw the structure of reaction product E.

b) Provide the reaction mechanism and explain the selectivity of the reaction.

Basically,the reaction that occur is an elimination reaction as it looks like 3

fundamental things of an elimination reaction occur such as 1) removal of proton, 2)
C-C pi bond is formed and 3) there is a breakage in the bond of the leaving group.

The reaction happen by Zn attack the Br on the substituent chain as Zn is a base

and tend to act as a nucleophile and Br is soft acid.The selectivity of the reaction
probably because, Zn preferably did not attack F because of F is a hard acid and is
highly charged density.

Generally, Br is a good leaving group.An E1 elimination step seems to happen by the

breaking bond of -Br-Zn and F groups.Hence gives the final product in F.
SIC 2002 Assignment 2020/21(S1)

(10 marks)

3. Consider the following reaction.

HBr (aq)

G+H+K
OH
F1
O
L
1 product
O
F2

a) Provide the structures of products G, H and K.

b) Which will be the major reaction product? Explain.

Compound K will be the major product since the product is from a 3° carbocation
intermediate and generally a tertiary carbocation,3° is more stable than 1° and 2°
carbocation.So the reaction will prefer this step of reaction as major product.

c) Which of the substrates, F1 and F2, is more reactive? Explain.

F1 is an alcohol while F2 is an ester.F2 is more reactive than F1 because basically it

has a functional group of carbonyl which is known more reactive than alcohol.In
addition,.ester is a good leaving group as it is a weak base.Alcohol is a strong base
thus it is a bad leaving group.
SIC 2002 Assignment 2020/21(S1)

d) Provide reaction conditions L to obtain a single reaction product from F2. Explain.

The reaction is effective for non-acidic condition such as NaOH or KOH in order to
prevent the increasing of the acidity of the alcohol and result into an alcoholate
instead of carbanion.

(10 marks)
SIC 2002 Assignment 2020/21(S1)

4. Consider the following reaction.

N P
M X N
 

X = Cl, Br, I

a) Provide the structures of products M and N and specify the respective reaction type.
Explain your answer.

• Both step in the reaction are nucleophilic substitution reaction since the
electron pairs on the electronegative nitrogen and phosphorus are attracted
to the positive carbon-halogen bond in the halogenalkane.

• The lone pair of electrons at Nitrogen and Phosphorus act as nucleophile

and attack at the electrophilic side of the carbon that attached to halogen
(carbon-halogen bond).

• Single step process where the formation bond and cleavage bond occur in
the same time.

• The reaction pathway occur in SN2 mechanism.

b) Sort the different halide substrate according to increasing reactivity. Explain.

The order of the ability of the leaving group is I > Br > Cl. This is because I have the
largest orbital size and the distance between atomic centre and effective centre in
terms of electrostatic interactions is longer. This results a weaker interaction for the
partial charges.And also, as the size increases, the basicity decreases and the weak
bases are the best leaving group.Hence, the better leaving group the more reactivity.

(10 marks)