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Topic: sodium azide reaction  (Read 6063 times)

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Offline robvba

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sodium azide reaction
« on: April 05, 2009, 05:35:22 PM »
1,3-dibromo-3-methylpentane + N3- (in THF) ::equil:: a six member ring structure consisting of three Ns?
sodium azide is a weak base, so it will displace the brimine. however, will it form a ring?

Offline 408

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Re: sodium azide reaction
« Reply #1 on: April 05, 2009, 06:55:01 PM »
No, it will displace the bromine because it is a really strong nucleophile. Not because it is a weak base.

Look at it SN2ing off the terminal Br, and then the lone pair on the other side of the azide(formally - charged) knocking off the central Bromide ion.  Follow it up with the Br- ion eliminating the proton on carbon one with e- pushing taking care of the positive charge on the central N...and you get your desired cpd.

Offline robvba

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Re: sodium azide reaction
« Reply #2 on: April 05, 2009, 07:30:19 PM »
makes sense. thank you

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