Heterocyclic Chemistry 1, Semester 2, 2013 (06522)

2.

Answer ALL of the following parts.

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

For TWO of the following sections (i)-(iii) work out the structure of the
unknown product. In each case draw key intermediates to justify your answer
(mechanisms are not required).
H2S

(i)

C
H+ cat.

(ii)

C11H14S

O
+

2 eq.

pH 8.5

O
1 eq.

D
H

Ph

NH3

C17H19NO2

(iii)

O
O

+
O

H+ cat.

E
C14H23NO2

NH2

(2 5 marks)

Heterocyclic Chemistry 1, Semester 2, 2013 (06522)

MODEL ANSWER
(d)

For TWO of the following sections (i)-(iii) work out the structure of the
unknown product. In each case draw key intermediates to justify your answer
(mechanisms are not required).
H2S

(i)

H+ cat.

SH O

(ii)

2 eq.

Ph

Ph

1 eq.
H

Ph

pH 8.5

O
+

OH

NH3

Ph

N
H

Ph

+
H2N

N
HO H

O H2N

(iii)

O
O

H+ cat.

+
O

N
H

NH2

O
O
N

O
OH

O
O

O
N
H

O
N
H