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JEE Main · 2009 · 12 Apr 2009 · Offline · General Organic Chemistry

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Arrange the carbanions, , in order of their decreasing stability :
  1. (A)
  2. (B)
  3. (C)✓ Correct
  4. (D)

Answer: (C)

Solution

A carbanion is more stable when the negative charge is drawn away or spread out, so electron-withdrawing groups help and electron-donating alkyl groups hurt. The trichloromethyl carbanion is steadied most strongly by the inductive pull of its three chlorines, the benzyl carbanion is stabilised by delocalisation into the ring, and between the alkyl carbanions the secondary one is more stable than the tertiary because it carries fewer electron-pushing methyl groups. The decreasing order of stability is thus .

JEE Main · 2009 · 12 Apr 2009 · Offline · Single correct option

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