Practicing Success
The solution of (+)-2-chloro-2-phenylethane in toluene racemizes slowly in the presence of small amount of SbCl5; due to the formation of |
carbanion carbene free radical carbocation |
carbocation |
The correct answer is option 4. carbocation. SbCl5 is a Lewis acid, which means that it can accept a pair of electrons. When it reacts with (+)-2-chloro-2-phenylethane, it accepts the electron pair from the chlorine atom, forming a carbocation. The carbocation is a planar molecule, so the chloride ion can attack from either side, resulting in a racemic mixture. The other options are incorrect. Carbanion: A carbanion is a negatively charged carbon atom with three bonds. It is not formed in this reaction. Carbene: A carbene is a neutral carbon atom with two unbonded electrons. It is not formed in this reaction. Free radical: A free radical is an atom or molecule with an unpaired electron. It is not formed in this reaction. Therefore, the carbocation is formed in the reaction of (+)-2-chloro-2-phenylethane with SbCl5, resulting in racemization. |