Writing Reaction Mechanism
1.
Predict the major product from the reaction of the following alkene with HCl. Propose a
reaction mechanism for its formation.
CH3CH2CH=C(CH3)2
2.
O
CH3
D
H3C
HBr
D
D
CH3CO2H,
D
Br
40oC
H3C
D
D
+
H
OCCH3
D
D
D
Major
H
Minor
a) Propose the reaction mechanism for the formation of the major product.
b) Propose the reaction mechanism for the formation of the minor product.
3. Reaction of 1-phenylpropene and dilute sulphuric acid yields only 1-phenylpropanol.
Propose a mechanism for the reaction and explain why this is the only isomer produced.
OH
H2O
H2SO4
4.
Triphenylmethane can be prepared by reaction of benzene and trichloromethane in the
presence of AlCl3. Propose a mechanism for the reaction.
+
5.
AlCl3
CHCl3
H
Propose a mechanism to account for the reaction of benzene with
2,5-dichloro-2,5-dimethylhexane.
1
Cl
+
AlCl3
Cl
6.
Write a possible reaction mechanism for the following reaction.
O
O
Cl
+
N
NH
O
O
7.
Methamphetamine can be synthesized by first reacting phenyl-2-propanone with
methylamine. Propose a reaction mechanism of initial reaction for the formation of
the intermediate as shown below.
CH3NH2
HO
O
NHCH3
NHCH3
Methamphetamine
8.
Write a reaction mechanism for the following reaction.
CH3
Br2
Br
hv
Br
CH3
9.
Suggest a mechanism for the following transformation.
H+
HO
O
OH
CHO
10.
In solid phase synthesis of peptides, the amino group in the amino acid is normally
protected by the following reaction. Propose a mechanism for the transformation.
NH2
O
O
O
O
O
HN
O
CO2Et
O
CO2Et
2