Pushing Electrons
4th Edition
ISBN:9781133951889
Author:Weeks, Daniel P.
Publisher:Weeks, Daniel P.
Chapter3: Mechanisms
Section: Chapter Questions
Problem 96EQ
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What is the likely mechanism of nucleophilic substitution for attached alkyl halide?

Br
Transcribed Image Text:Br
Expert Solution
Step 1

Alkyl halides undergo nucleophilic substitution reactions. Nucleophilic substitution reactions are reactions where a nucleophile ( species that are negatively charged ) with an abundance of electrons, replace a leaving group by reacting with an electrophile ( species that are positively charged ) that has a dearth of electrons. 

Step 2

Nucleophilic substitution reactions are basically of two types-

(1) SN1 reaction

SN1 reactions are called Nucleophilic substitution unimolecular reactions. The rate of the reaction depends on the concentration of only one species. The first step of these reactions is the formation of a carbocation by the loss of the leaving group. The next step includes the attack of the nucleophile to form the required product. Since tertiary carbocations are most stable thus, the reactivity order of carbocations in the decreasing order is-

tertiary carbocation > secondary carbocation > primary carbocation

 

(2) SN2  reactions are called Nucleophilic substitution bimolecular reactions. The first step includes the formation of a transition state with the nucleophile that attacks from the backside and the second step includes the loss of the leaving group. Both the first and second step occurs in a concerted mechanism. The reactivity order of carbocations in the decreasing order is-

primary carbocation > secondary carbocation > tertiary carbocation

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