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Which of the following compounds does NOT show resonance?

1. CH3CH2-O-CH=CH2 (ethyl vinyl ether)
2. Benzyl alcohol (C6H5-CH2-OH)
3. CH3CH2CH2-C(=O)-NH2 (butanamide)
4. CH3CH2-CH=CH-CH2-NH2

Correct answer: CH3CH2-CH=CH-CH2-NH2

Solution

In ethyl vinyl ether the oxygen lone pair conjugates with the vinyl C=C. In benzyl alcohol the benzene ring itself is a resonance system. In butanamide the amide nitrogen lone pair conjugates with the C=O. In CH3CH2-CH=CH-CH2-NH2 the C=C and the -NH2 are separated by a saturated sp3 CH2, so there is no conjugation between them and no resonance involving these groups.

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