Problems and exercisesSubstitution of Alcohols

1. Products with HBr

Give the main product of the reaction with HBr of:

1. 2-Methyl-2-propanol
2. 1-Butanol
3. 3,3-Dimethyl-2-butanol

2. Without rearrangement

How would you obtain 2-bromo-3-methylbutane from 3-methyl-2-butanol without rearrangement?

3. Thionyl chloride

Which by-products are formed in the reaction of an alcohol with SOCl₂ in pyridine? Why is this reagent convenient?