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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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Most popular questions from this chapter

Question: Treatment of alkenes A and B with HBr gives the same alkyl halide C. Draw a mechanism for each reaction, including all reasonable resonance structures for any intermediate.

Question: The major product formed by addition of HBr to CH32C=CH-CH=CCH32 is the same at low and high temperature. Draw the structure of the major product and explain why the kinetic and thermodynamic products are the same in this reaction

Question: Draw the products formed when each diene is treated with one equivalent of HCl.

a.

b.

c.

d.

Question: Addition of HCl to alkene X forms two alkyl halides Y and Z.

a. Label Y and Z as a 1,2-addition product or a 1,4-addition product.

b. Label Y and Z as the kinetic or thermodynamic product and explain why.

c. Explain why addition of HCl occurs at the indicated C=C(called an exocyclic double bond), rather than the other C=C (called an endocyclic double bond).

Question: Rank the following dienes in order of increasing heat of hydrogenation.
See all solutions

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