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PROBLEM 7.21

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Organic Chemistry
Found in: Page 268

Short Answer

Question: Which compound in each pair undergoes a faster SN2 reaction?

a.

and

b.

and

a. The compound mentioned below undergoes a faster SN2 reaction.

b.The structure provided below undergoes a faster SN2 reaction.

See the step by step solution

Step by Step Solution

  SN2 reaction

The SN2 reaction involves two steps, and a carbocation is not created in this reaction. Their reactions occur smoothly with unhindered halides as a hindered substrate makes the nucleophilic attack more difficult.

Compound that undergoes faster SN2  reaction in question a

The reaction rate of SN2 reaction depends on the nature of the alkyl halide. The SN2 reaction occurs faster in less bulky and unhindered alkyl halides. In the compounds given in the question, one is a primary alkyl halide, and the other is a secondary alkyl halide. The rate of SN2 reaction is faster for a primary halide. Hence, the compound showing a more rapid SN2 reaction is illustrated below:

Compound exhibiting faster SN2 reaction in question a

Compound that undergoes faster SN2  reaction in question b

The reaction is more rapid for an unhindered alkyl halide than a hindered alkyl halide. One of the compounds in question b is a secondary halide, and the other is a tertiary halide.

Tertiary halides do not undergo reaction because of the bulky groups present in them. The compound that exhibits a faster reaction is provided below:

Compound exhibiting faster reaction in question b

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