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Asked Dec 8, 2019
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Why do reactions like this require a polar protic solvent even though they mechanistically follow an SN2 pathway?

(e)
HS-
CH;CI
CH3SH
CH;OH
SN2
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(e) HS- CH;CI CH3SH CH;OH SN2

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Step 1

Polar protic solvents are the solvents which have tendency to solvate a nucleophile with the help of hydrogen bonding. The nucleophilicity of a nucleophile decreases and thereby, reactivity in the presence of a polar protic solvent in SN2 reactions.

In spite of this fact, , some larger nucleophiles that has high polarizability and more diffused electrons have lesser tendency to get solvated in the presence of a polar protic solvent through hydrogen bonding. Therefore, for such types of nucleophiles, the nucleophilicity increases in the presence of a polar protic solvent.

Step 2

In the given reaction, methyl chloride undergoes a nucleophilic substitution by SH- ion in the presence of methanol as a solvent. Here, SH- acts as a nucleophile and Cl- acts as a leaving group.

A polar protic solvent is required in this reaction because the nucleophile...

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