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document Dehydration of Alcohols
The dehydration of alcohols is both regioselective and stereoselective.  Regioselectively, explained by the Zaitsev Rule, the major product is always the more highly substituted alkene (alkene stability is increased by inductive and hyperconjugative electron donation to the electron deficient...
27 May, 2011 Comments: 0
document Student Question: Rearrangement in E1 and E2 - When does rearrangement occur in alcohol dehydration? When does it occur in alkyl halide dehydrohalogenation? For example, can rearrangement change a primary carbocation to a tertiary carbocation? Would that allow the reaction to have an E1 mechanism instead of an E2?
When does rearrangement occur in alcohol dehydration? Because alcohol dehydration is an elimination reaction, rearrangement occurs when a carbocation intermediate or partial carbocation (as in the transition state of an E2 type dehydration) occurs during elimination.  If this carbocation...
29 May, 2012 Comments: 0

Department of Chemistry & Chemical Biology