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Phthalimide undergoes the following sequence of reactions: first treatment with KOH, then with benzyl chloride. The product obtained is labeled P. How many total pi bonds are present in product P?

1. 5
2. 6
3. 8
4. 10

Correct answer: 8

Solution

Treatment of phthalimide with KOH gives the potassium salt, which on reaction with benzyl chloride (Gabriel synthesis) gives N-benzylphthalimide. This molecule has 3 pi bonds in the phthalimide benzene ring, 2 C=O pi bonds in the imide, and 3 pi bonds in the benzyl phenyl ring, totalling 8 pi bonds.

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