MEDIUMMCQ SINGLEIChO (Chemistry Olympiad)Inorganic ChemistryAlkyl and Aryl HalidesE elimination follows an antiperiplanar structure

Which one is most reactive towards SN1 reaction? (AIPMT 2011)

A.C6H5CH(C6H5)Br

B.C6H5CH(CH3)Br

C.C6H5C(CH3)(C6H5)Br✓ Correct

D.C6H5CH2Br

Explanation

SN1 reactions proceed via the formation of a carbocation intermediate. More stable is the carbocation more reaction more reactive is the alkyl/aryl halide towards SN1. In C6H5C+(CH3)(C6H5) carbocation, the two phenyl rings by their –R effect and –CH3 by its +I effect diminish the positive charge and make it stable.

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