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  4. A solution of (-)-1-chloro-1-phenylethane in toluene racemises slowly in the presence of a small amount of SbCl5 , due to the formation of :

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Q. A solution of (-)-1-chloro-1-phenylethane in toluene racemises slowly in the presence of a small amount of SbCl5 , due to the formation of :

NTA AbhyasNTA Abhyas 2020Organic Chemistry – Some Basic Principles and Techniques

Solution:

(-) - 1 - chloro - 1 - phenyl ethane Solution

Solution

with SbCl5 carbocation is formed. As the carbocation in planar, $\text{Cl}^{\ominus}$ can again attack from both sides giving racemic mixture. (d, l formed)