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Chapter 16: PROBLEM 16.62 (page 638)

Question: Which benzylic halide reacts faster in an SN1 reaction? Explain

Short Answer

Expert verified

Answer

Compound A

Step by step solution

01

SN1 mechanism 

TheSN1 reaction forms a stable carbocation.

The more stable the carbocation, the faster is the reactivity of SN1 mechanism.

02

Benzylic halide

Benzylic halide is the most stable carbocation. The electron-withdrawing groups decrease the stability of the carbocation, whereas the electron-donating groups increase it.

03

Explanation

Benzylic halide A reacts faster in theSN1 reaction. In compound A, the para position is occupied by the methoxy group, which is an electron donor for ortho-para positions through the delocalization of electrons.

In compound B, the para position is occupied by the CHO group which is electron-withdrawing at ortho-para positions.

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