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A set of three nucleophilic displacement reactions is shown below: CH3 CH2CI CI Cl CH3 H20, CH3CH20H SN1 reaction Which reaction (A, B, or C) proceeds the fastest? Which reaction (A, B, or C) proceeds the slowest? A set of three nucleophilic displacement reactions is shown below CH3 CH3 CH3Br CH3CHCH2CH2Br CH3CHCHBr 0% CH3 Nal acetone SN2 reaction Which reaction (A, B, or C) proceeds the fastest? Which reaction (A, B, or C) proceeds the slowest?

Chemistry Jan 25, 2021

A set of three nucleophilic displacement reactions is shown below: CH3 CH2CI CI Cl CH3 H20, CH3CH20H SN1 reaction Which reaction (A, B, or C) proceeds the fastest? Which reaction (A, B, or C) proceeds the slowest?
A set of three nucleophilic displacement reactions is shown below CH3 CH3 CH3Br CH3CHCH2CH2Br CH3CHCHBr 0% CH3 Nal acetone SN2 reaction Which reaction (A, B, or C) proceeds the fastest? Which reaction (A, B, or C) proceeds the slowest?

Expert Solution

In SN1 reaction, rate of reaction depends upon stablity of carbocation. Stablity order is 3o>2o>1o

A forms 3o carbocation and hence will proceed fastest. B forms 1o carbocation and will proceed the slowest.

In SN2, the rate of reaction depends on stablity of transition state. For SN2 stablity order is 3o<2o<1o . Another factor is steric hinderance. For more rate less steric hinderence should be there.

A is 1o so it will proceed the fastest. B is also 1o but it has more steric hinderance compared to A. C is 2o so it will proceed with slowest rate.

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