4-Bromo-2-nitroaniline (a ring bearing -NH_2, -Br and -NO_2) is subjected to the sequence (i) diazotisation, (ii) CuCl I; I Sn/HCl II; II [ (ii) H_3PO_2] (i) diazotisation III. The final product (III) obtained is

JEE Main Chemistry question

4-Bromo-2-nitroaniline (a ring bearing , and ) is subjected to the sequence (i) diazotisation, (ii) CuCl I; I II; II III. The final product (III) obtained is

(A)a ring bearing two substituents and one substituent, with the original nitro-derived position now unsubstituted (H)Correct
(B)a ring bearing two substituents with the group still intact
(C)a ring bearing , , on three consecutive positions
(D)None of these

Answer: (A)

Solution

Diazotisation and Sandmeyer substitution with CuCl converts the original group into (step to I, Br and NO2 untouched). then reduces the nitro group to a new (step to II). A second diazotisation followed by reductive deamination with

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Question ID VK-150357