Master Organic Chemistry Reaction Guide

SN2 reaction of hydrosulfide ion with alkyl halides to give thiols

Description: Alkyl halides (or tosylates) will react with the hydrosulfide ion (HS–) to give thiols.

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Real-Life Example:

Org. Synth. 1932, 12, 68
DOI Link: 10.15227/orgsyn.012.0068

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3 thoughts on “SN2 reaction of hydrosulfide ion with alkyl halides to give thiols

    1. A polar aprotic solvent like DMSO or acetonitrile would certainly be helpful for these reactions. It’s unlikely to have any competition with the E2 since the sulfide anion is not particularly basic (good threshold is the E2 doesn’t compete if the pKa of the conjugate acid is 12 or below. Thiols have a pKa of 12).

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