Answer to Question #116500 in Organic Chemistry for Tiffany Steytler

Question

On which ring and at what position(s) of the compounds shown below will
electrophilic aromatic substitution take place? Explain your answer in detail.
(a)
C N
H
H3C
O
(b)
C N
H
O
O2N
CH3
(5)
2.3) The following scheme is proposed for the synthesis of 4-bromobenzoic acid:
NH2 NH2
Br2
i) NaNO2
/HCl
ii) CuCN
Br
CN
Br
CN
Br
H3O
+
Briefly discuss the limitations of the above scheme and then propose a route
that would accomplish the desired product.

Answer 1

b)