Br or Br

Pushing Electrons
4th Edition
ISBN:9781133951889
Author:Weeks, Daniel P.
Publisher:Weeks, Daniel P.
Chapter3: Mechanisms
Section: Chapter Questions
Problem 111EQ
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Which compound in attached pair undergoes a faster SN2 reaction?

Br or
Br
Transcribed Image Text:Br or Br
Expert Solution
Step 1

SN2 reaction is the bimolecular nucleophilic substitution reaction. This type of mechanism does not involve the formation of carbonation. The bond-forming and breaking take place simultaneously. Inversion of configuration occurs in this mechanism. It follows the order i.e 1o>2o>3o.

 

Step 2

To determine which compound undergoes SN2 faster.

The SN2 reaction is faster in 2o as compared to 3o. In the bromocyclohexane, the carbon atom attached to the halogen atom is further attached to two substituents shown by two dashed lines. Hence, it is 2o. In the 1-bromo-1-methylcyclohexane, the carbon atom attached to the halogen atom is further attached to three substituents shown by three dashed lines. Hence, it is 3o.

Chemistry homework question answer, step 2, image 1

Bromocyclohexane goes faster in 2o.

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