School of Physical & Mathematical Sciences

Division of Chemistry & Biological Chemistry

H3 Organic Synthesis and Mechanism - Tutorial 2

Reaction Mechanism

1) Fill in the curved arrows or the missing products for the following one-step
reactions:
O O

H O H H H +
+ O O O

+ I HO OH 2 HO
I

H O + Br HO + Br

O O

CH2 CH2

O
+

Br

+ H Br

CH3
O CH3
+
O O O
H
H

O O
H O HO + O
O

OH

N + OH
N

CO2CH3 CO2CH3

H3C H 3C
S S
School of Physical & Mathematical Sciences
Division of Chemistry & Biological Chemistry

2) Draw as many resonance structure as possible for the following

compounds:
NH2
H 2N H N
C
NH2 H
H 2N
H

3) Compound A is converted to compound G and the energy diagram is as

shown:
Energy

Reaction progress

a) Which are the intermediates and which are the transition states?
b) How many steps are there in the reaction mechanism?
c) Is the reaction exergonic or endergonic?
d) How would the rate of reaction be affected if A is made less stable
without affecting the energy of the rest of the intermediates and
product?
e) How would Keq be affected if A is made more stable without affecting
the energy of the rest of the intermediates and product?