Ace Your Next Organic Chemistry Exam.

With these Downloadable PDF Study Guides

Our Study Guides

SN2 reaction of water with alkyl halides to give alcohols

Description: Primary or methyl halides (or tosylates) will react with water to give alcohols. This is an SN2 reaction.
[private_ReactionGuide]

1-header

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

Examples: 

2-examples

Notes: Water is a poor nucleophile and generally isn’t strong enough to displace a leaving group from a secondary alkyl halide.

Mechanism: In this reaction water attacks the carbon in an SN2 reaction displacing the leaving group (bromide in this case) (Step 1, arrows A and B). The bromide ion then removes a proton from the oxygen, providing the neutral alcohol and HBr.

3-mech

Notes: It’s also reasonable to use water as the base here in the second step instead of Br(-). In fact it’s probably more reasonable to do so since water is a stronger base than Br(-).

 

[/private_ReactionGuide]