Question

Predict the order of reactivity of the following compounds by S_Nl reaction mechanism.

\[\ce{\underset{\text{(I)}}{C6H5CH(C6H5)Cl}}\]

\[\ce{\underset{\text{(II)}}{C6H5CH2Cl}}\]

\[\ce{\underset{\text{(III)}}{C6H5C(CH3)(C6H5)Cl}}\]

Options

• I < II < III

• III < I < II

• II < I < III

• III < II < I

Answer 1

II < I < III

Explanation:

The reactivity towards S_Nl reaction mechanism follows the order:

\[\ce{\underset{\text{Forms 1° carbocation (II)}}{C6H5CH2Cl} < \underset{\text{Forms 2° carbocation (I)}}{C6H5CH(C6H5)Cl} < \underset{\text{Forms 3° carbocation (III)}}{C6H5C(CH3)(C6H5)Cl}}\]