Heterocyclic Chemistry 1, Semester 2, 2012 (06522)

1.

Answer ALL of the following parts.

(a)-(d) RWB questions.
(e)

For TWO of the following sections (i)-(iii) work out the structure(s) of the
unknown product(s). In each case draw key intermediates to justify your
answer (full mechanisms are not required).
O

NH2NH2, cat. H+

(i)

(i) NH2NH2, cat. H+

(ii) oxidation

(ii)

G
C7H10N2

(iii)

C7H12N2

NH2NH2, cat. H+

E
C7H12N2

H
C7H12N2

J
C7H9N

(2 5 marks)

Heterocyclic Chemistry, Semester 2, 2011 (06522)

MODEL ANSWER
(e)

For TWO of the following sections (i)-(iii) work out the structure(s) of the
unknown product(s). In each case draw key intermediates to justify your
answer (full mechanisms are not required).
O

NH2NH2, cat. H+

(i)

NH2NH2, cat. H+

E
C7H12N2

N NH

C
H2N

C7H12N2

HN N

N NH

OH

+
O

NH2

HN N
HO

(i) NH2NH2, cat. H+

(ii) oxidation

(ii)
O

C7H10N2

O
N
F

(ii) oxidation

O
H2N

NH2

O
(i) NH2NH2, cat. H+

H2N

H
C7H12N2

HN

H
N
OH

HN

H
N
NH2

NH

N
OH
O

NH2NH2, cat. H+

(iii)

C7H9N

I
O

O
N

I
H2 N

J
N

- NH3

H2 N

NH

H 2N

OH
N

H2N