What is the purpose of CH3OH being the solvent? Isn't CH3S- the only reagent needed in order to go through an SN2 reaction with the replacement of the bromine?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter18: Ethers And Epoxides; Thiols And Sulfides
Section18.SE: Something Extra
Problem 59GP: Meerwein's reagent, triethyloxonium tetrafluoroborate, is a powerful ethylating agent that converts...
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What is the purpose of CH3OH being the solvent? Isn't CH3S- the only reagent needed in order to go through an SN2 reaction with the replacement of the bromine?

Because sulfur is larger and more polarizable than oxygen, thiolate ions are even
better nucleophiles than alkoxide ions. Thiolates are such effective nucleophiles that
secondary alkyl halides often react to give good yields of SN2 products.
Br H
H SCH3
C
CH3
C
CH₂CH3
(R)-2-bromobutane
CH₂S-Na+
CH₂OH
CH₂CH3
(S)-2-(methylthio)butane
CH3
Transcribed Image Text:Because sulfur is larger and more polarizable than oxygen, thiolate ions are even better nucleophiles than alkoxide ions. Thiolates are such effective nucleophiles that secondary alkyl halides often react to give good yields of SN2 products. Br H H SCH3 C CH3 C CH₂CH3 (R)-2-bromobutane CH₂S-Na+ CH₂OH CH₂CH3 (S)-2-(methylthio)butane CH3
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