DAT destroyer OChem #77 (2011 version)

[DentistDMD]

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Shouldn't there be a double bond between a tertiary carbon and a secondary carbon, not between a tertiary and primary carbons after the bromine leaves?

 

[Dew517]

Tert-but Oxide will eliminate to give the Hoffman product or the less substituted alkene - the primary-tertiary in this case as opposed to the secondary-tertiary.

 

[LaughingGas]

Shouldn't there be a double bond between a tertiary carbon and a secondary carbon, not between a tertiary and primary carbons after the bromine leaves?

You know the tert-butoxide ion in tert-butanol is a very BULKY BASE. Bulky base , which that causes to remove H from less stericically available space, which is the methyl group. Think about it, would a bulky base able to approach close enough to remove the H+ from secondary carbon? Probably not, so that causes to do an Anti-Zaitsev elimination. Hope that is clear enough..