The compound shown is treated with concentrated aqueous KOH. After deprotonation, loss of chloride from the trichloromethyl anion gives a neutral reactive intermediate with a divalent carbon atom. Which structure shown is this intermediate?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

The compound shown is chloroform. Base removes H

^{+}

to give the trichloromethyl anion, which loses

Cl X^{-}

by alpha-elimination. The product is dichlorocarbene,

: CCl X_{2}

, a neutral divalent carbon species with six valence electrons; the anion and cation drawn have an extra Cl and a charge, and the last structure is a radical.

Practice General Organic Chemistry III: Reaction Intermediates More on Stability ranking of drawn radicals, carbanions and carbenes

Previous questionNext question

The compound shown is treated with concentrated aqueous KOH. After deprotonation, loss of chloride from the trichloromethyl anion gives a neutral reactive intermediate with a divalent carbon atom. Which structure shown is this intermediate?

Answer: C

More questions on Stability ranking of drawn radicals, carbanions and carbenes