Chapter 9.13, Problem 23P

Interpretation Introduction

(a)

Interpretation: The products of the given reaction are to be drawn by indicating the stereochemistry at any stereogenic center.

Concept introduction: Alcohols are converted into alkyl tosylates by treatment with $p\text{-toluenesulfonyl}\text{chloride}\left(\text{TsCl}\right)$ in the presence of pyridine. The overall reaction converts ${}^{-}\text{OH}$ (a poor leaving group) into ${}^{-}\text{OTs}$ (a good leaving group). The stereochemistry of the reaction is retention of configuration.

Interpretation Introduction

(b)

Interpretation: The products of the given reaction are to be drawn by indicating the stereochemistry at any stereogenic center.

Concept introduction: Alcohols are converted into alkyl tosylates by treatment with $p\text{-toluenesulfonyl}\text{chloride}\left(\text{TsCl}\right)$ in the presence of pyridine. The overall reaction converts ${}^{-}\text{OH}$ (a poor leaving group) into ${}^{-}\text{OTs}$ (a good leaving group). The stereochemistry of the reaction is retention of configuration.