Chapter 8, Problem 8.65SP

(a)

Interpretation Introduction

To determine: The conversion of fumaric acid to $(\pm )-\text{tartaric}\text{acid}$.

Interpretation: The given question stated that two butenedioic acids are called fumaric acids (trans) and maleic acid (cis) and $2,3-\text{Dihydroxybutanedioic}\text{acid}$ is called tartaric acid. The given conversion is to be predicted.

Concept introduction: Osmium tetroxide also called osmic acid reacts with alkenes to form cyclic osmate ester. Hydrogen peroxide is used as an oxidizing agent to hydrolyze the osmate ester. The attack of oxygen from osmic acid to the double bond of alkene is from the same side. Thus they have syn stereochemistry.

(b)

Interpretation Introduction

To determine: The conversion of fumaric acid to meso-tartaric acid.

Interpretation: The given question stated that two butenedioic acids are called fumaric acids (trans) and maleic acid (cis) and $2,3-\text{Dihydroxybutanedioic}\text{acid}$ is called tartaric acid. The given conversion is to be predicted.

Concept introduction: Epoxidation of alkene is an oxidation process. Epoxides are also called an oxirane and they are intermediates that are used to convert alkenes into other functional group. Peroxyacid is used to convert alkene into an epoxide.

The steps followed by the given reaction are stated as:

• First step is the formation of epoxide.
• Second step is the attack of water to opens the ring.
• The third step is deprotonation that gives diol product.

(c)

Interpretation Introduction

To determine: The conversion of maleic acid to $(\pm )-\text{tartaric}\text{acid}$.

Interpretation: The given question stated that two butenedioic acids are called fumaric acids (trans) and maleic acid (cis) and $2,3-\text{Dihydroxybutanedioic}\text{acid}$ is called tartaric acid. The given conversion is to be predicted.

Concept introduction: Epoxidation of alkene is an oxidation process. Epoxides are also called an oxirane and they are intermediates that are used to convert alkenes into other functional group. Peroxyacid is used to convert alkene into an epoxide.

The steps followed by the given reaction are stated as:

• First step is the formation of epoxide.
• Second step is the attack of water to opens the ring.
• The third step is deprotonation that gives diol product.

(d)

Interpretation Introduction

To determine: The conversion of maleic acid to meso-tartaric acid.

Interpretation: The given question stated that two butenedioic acids are called fumaric acids (trans) and maleic acid (cis) and $2,3-\text{Dihydroxybutanedioic}\text{acid}$ is called tartaric acid. The given conversion is to be predicted.

Concept introduction: Osmium tetroxide also called osmic acid reacts with alkenes to form cyclic osmate ester. Hydrogen peroxide is used as an oxidizing agent to hydrolyze the osmate ester. The attack of oxygen from osmic acid to the double bond of alkene is from the same side. Thus, they have syn stereochemistry.