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Arrange the following compounds in order of decreasing basic strength: (P) Acetanilide (C6H5NHCOCH3), (Q) Benzylamine (C6H5CH2NH2), (R) N-Methylaniline (C6H5NHCH3).

1. P > Q > R
2. Q > R > P
3. R > Q > P
4. R > P > Q

Correct answer: Q > R > P

Solution

Q (benzylamine, C6H5CH2NH2) is most basic because the nitrogen is not directly attached to the benzene ring — it behaves like an aliphatic amine with only inductive withdrawal. R (N-methylaniline) has nitrogen directly on the ring with partial lone pair delocalization (weaker than in amide), moderately basic. P (acetanilide) has nitrogen lone pair strongly delocalized into the C=O group of the amide, making it least basic. Order: Q > R > P.

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