SN2 reaction of carboxylate ions with alkyl halides to give esters

by James

Description: Alkyl halides (or tosylates) will react with carboxylate ions to form esters. This is an SN2 reaction. [private_ReactionGuide]

Notes: X here is a halide (Cl, Br, I) or sulfonate (OTs, OMs)

The counter-ion on the carboxylate can be any alkali ion, such as Li, Na (pictured) or K.

Examples: 

Notes: Note that since this is an SN2 reaction and proceeds via backside attack, there will be inversion of configuation at the carbon (note the last two examples).

Mechanism: In the SN2 reaction the nucleophile (RCOO-) attacks the carbon with the good leaving group, forming a C–O bond and breaking the C–Br bond (Step 1, arrows A and B).

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