Chapter 21, Problem 21.49P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism and the major organic product for given reaction is to be drawn.

Concept introduction:

Sulfonyl chloride has the general form ${\text{R-SO}}_{\text{2}}\text{Cl}$. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the $\text{S=O}$ group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor ${\text{HO}}^{\text{-}}$ leaving group into a great ${\text{RSO}}_{\text{3}}{}^{\text{-}}$ leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the $\text{C-OH}$ carbon.

Interpretation Introduction

(b)

Interpretation:

The complete mechanism and the major organic product for given reaction is to be drawn.

Concept introduction:

Sulfonyl chloride has the general form ${\text{R-SO}}_{\text{2}}\text{Cl}$. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the $\text{S=O}$ group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor ${\text{HO}}^{\text{-}}$ leaving group into a great ${\text{RSO}}_{\text{3}}{}^{\text{-}}$ leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the $\text{C-OH}$ carbon.

Interpretation Introduction

(c)

Interpretation:

The complete mechanism and the major organic product for the given reaction is to be drawn.

Concept introduction:

Sulfonyl chloride has the general form ${\text{R-SO}}_{\text{2}}\text{Cl}$. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the $\text{S=O}$ group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor ${\text{HO}}^{\text{-}}$ leaving group into a great ${\text{RSO}}_{\text{3}}{}^{\text{-}}$ leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the $\text{C-OH}$ carbon.