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 :
free radical
carbanion
carbene
carbocation
As we have learnt,
Racemisation take place when an optically active species undergoes at the chiral carbon.
There is formation of a carbocation and the attack of the nucleophile can take place from both above the plane as well as below the plane to obtain an equimolar mixture of enantiomers leading to Racemisation.
1-chloro - 1 - phenylethane on treatment with SbCl5 :
Therefore, option(4) is correct.