SN2 reaction between azide ion and alkyl halides to give alkyl azides

by James

Description: Alkyl halides (or tosylates) will react with azide ions (such as NaN3 or KN3) in an SN2 reaction to give alkyl azides.
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Notes: X here is a halide (Cl, Br, I) or sulfonate (OTs, OMs)

Although Na is often shown as the counter-ion any alkali metal can also be used (e.g. Li, Na, K)

Examples:

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

Mechanisms: In the SN2 reaction the nucleophile (N3-) attacks the carbon with the good leaving group, forming a C–N bond and breaking the C–I bond (Step 1, arrows A and B).

Notes: For more information on the SN2 see the summary sheet on this reaction. For our purposes using Na or K is immaterial.

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{ 1 comment… read it below or add one }

Andres Vanegas October 9, 2014 at 10:40 pm

Is an alkyl halide formation possible from an alkyl azide?

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