Chapter 8, Problem 47P

(a) Which primary alcohol of molecular formula ${\text{C}}_5{\text{H}}_{12}\text{O}$ cannot be prepared from an alkene by hydroboration–oxidation? Why?

(b) Write equations describing the preparation of three isomeric primary alcohols ofmolecular formula ${\text{C}}_5{\text{H}}_{12}\text{O}$ from alkenes.

(c) Write equations describing the preparation of the tertiary alcohol of molecular formula ${\text{C}}_5{\text{H}}_{12}\text{O}$ by acid-catalyzed hydration of two different alkenes.