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Which of the following amines is the strongest base?

1. (A) C6H5NH2 (aniline)
2. (B) C6H5NHCH3 (N-methylaniline)
3. (C) o-methylaniline (aniline with a methyl substituent on the ortho position of the ring)
4. (D) C6H5CH2NH2 (benzylamine)

Correct answer: (D) C6H5CH2NH2 (benzylamine)

Solution

In aniline-type compounds (A, B, C), the nitrogen lone pair is conjugated with the aromatic ring, making them weakly basic. In benzylamine (D), the sp3 CH2 group breaks this conjugation, so nitrogen retains full electron density. Benzylamine is the strongest base among the options.

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