The major product X formed in the following reaction sequence is : [figure]
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Answer
(3) [figure]
Solution
(i) In chlorination, -C2H5 (activating, o/p-directing) and -NO2 (deactivating, m-directing) both direct Cl to the carbon ortho to -C2H5 (meta to -NO2).
(ii) Sn/HCl reduces -NO2 to -NH2.
(iii) NaNO2/HCl at 273–278 K converts -NH2 into the diazonium salt -N2 Cl .
(iv) KI replaces -N2 by -I.
[figure]
X = 2-chloro-1-ethyl-4-iodobenzene
Answer: (3)