Dehydration of 3,3,-Dimethyl-2-Butanol-Example of molecular Rearrangement

Slide 31 of 39

Notes:

1. C(CH3)3-CH(OH)-CH3 + H3O + ---> C(CH3)3-CH(OH2 +)-CH3

2. C(CH3)3-CH(OH2 +)-CH3 ---> C(CH3)3-CH +-CH3 + H2O

3. C(CH3)3-CH +-CH3 -----> C + (CH3)2 -CH(CH3)2

4. C +(CH3)2 -CH(CH3)2 + H2O ----> CH3-C(CH3)=CH(CH3)2 (major product)

4’ C +(CH3)2 -CH(CH3)2 +H2O ----> CH2=C(CH3)-CH(CH3)2 (minor product)