Chapter 14, Problem 14.72P

Reaction of unknown A with $\text{HCl}$ forms chlorohydrin B as the major product. A shows no absorptions in its IR spectrum at $1700{\text{cm}}^{-1}$ or $3600\text{-}3200{\text{cm}}^{-1}$, and gives the following ${}^1\text{H}\text{NMR}$ data: $\text{1}\text{.4}\left(\text{doublet,}\text{3}\text{H}\right)$, $\text{3}\text{.0}\left(\text{quartet}\text{of}\text{doublets,}\text{1}\text{H}\right)$, $\text{3}\text{.5}\left(\text{doublet,}\text{1}\text{H}\right)$, $\text{3}\text{.8}\left(\text{singlet,}\text{3}\text{H}\right)$, $\text{6}\text{.9}\left(\text{doublet,}2\text{H}\right)$, and $\text{7}\text{.2}\left(\text{doublet,}2\text{H}\right)\text{ppm}$. (a) Propose a structure for A including stereochemistry. (b) Explain why B is the major product in this reaction.