Consider the compound shown. Select all the correct statements, comparing it with aniline and ammonia in water.

AIt is a stronger base than aniline
BIts nitrogen lone pair is delocalised into the benzene ring
CIts conjugate acid is a weaker acid than the anilinium ion
DWith cold $NaNO X_{2}$ / $HCl$ it gives a stable diazonium salt

Answer: A, C

The compound shown is benzylamine; the

CH X_{2}

insulates nitrogen from the ring, so the lone pair is localised (pKb about 4.7 against 9.4 for aniline). Hence it is a stronger base and its conjugate acid is a weaker acid than anilinium. Aliphatic primary amines such as this one do not give stable diazonium salts; they lose

N X_{2}

to give alcohol.

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Consider the compound shown. Select all the correct statements, comparing it with aniline and ammonia in water.

Answer: A, C

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