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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3nc164

Which of the following can be used to prepare aniline?

ANitrobenzene with $Sn / HCl$
BBenzamide with $Br X_{2} + NaOH$
CChlorobenzene with potassium phthalimide, followed by hydrolysis (Gabriel synthesis)
DBenzonitrile with $LiAlH X_{4}$

Answer: A, B

Nitrobenzene is reduced to aniline by Sn/HCl, and Hofmann bromamide degradation of benzamide gives aniline (one carbon less). The Gabriel synthesis fails for aryl halides because they do not undergo SN2 with the phthalimide anion. LiAlH4 reduces benzonitrile to benzylamine, which has one carbon more.

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