Chapter 21, Problem 21.61P

Interpretation Introduction

(a)

Interpretation:

The ketone or aldehyde that can be used to produce the given compound when treated with $\text{m-chlorobenzoic}$ acid under acidic condition is to be drawn.

Concept introduction:

${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ are acids and will react with a ketone or aldehyde in a Baeyer-Villiger oxidation. Baeyer–Villiger oxidation produces carboxylic acids from aldehydes, and esters from ketones. In these reactions, a hydrogen or alkyl group departs from the carbonyl carbon, facilitated by the breaking of the weak $\text{O-O}$ bond from peroxyacid $\left({\text{RCO}}_{\text{3}}\text{H}\right)$.

Answer to Problem 21.61P

The ketone that can be used to produce the given compound when treated with $\text{m-chlorobenzoic}$ acid under acidic condition is:

Explanation of Solution

The given compound is:

The given compound is an ester that can be produced when a ketone treated with the ${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ in a Baeyer-Villiger oxidation reaction. In a Baeyer-Villiger oxidation reaction, an O atom from the peroxyacid is inserted between the carbonyl C and one of the groups, initially bonded to the carbonyl C. To reserve the reaction, remove the oxygen next to the carbonyl C and re-form the C-C bond which is shown in red. The ketone that can be used to produce the given acid compound when treated with $\text{m-chlorobenzoic}$ acid under acidic condition is:

Conclusion

The ketone that can be used to produce the given compound is drawn, removing the oxygen next to the carbonyl C which is inserted when it reacts with ${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ and re-forms the C-C bond.

Interpretation Introduction

(b)

Interpretation:

The ketone or aldehyde that can be used to produce the given compound when treated with $\text{m-chlorobenzoic}$ acid under acidic condition is to be drawn.

Concept introduction:

${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ are acids and will react with a ketone or aldehyde in a Baeyer-Villiger oxidation. Baeyer–Villiger oxidation produces carboxylic acids from aldehydes, and esters from ketones. In these reactions, a hydrogen or alkyl group departs from the carbonyl carbon, facilitated by the breaking of the weak $\text{O-O}$ bond from peroxyacid $\left({\text{RCO}}_{\text{3}}\text{H}\right)$.

Answer to Problem 21.61P

The aldehyde that can be used to produce the given compound when treated with $\text{m-chlorobenzoic}$ acid under acidic condition is:

Explanation of Solution

The given compound is:

The given compound is an acid that can be produced when a aldehyde is treated with ${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ in a Baeyer-Villiger oxidation reaction. In Baeyer-Villiger oxidation reaction, an O atom from peroxyacid is inserted between the carbonyl C and one of groups initially bonded to the carbonyl C. To reserve the reaction, remove the oxygen next to the carbonyl C and re-form the C-H bond which is shown in red. The ketone that can be used to produce the given acid compound when treated with $\text{m-chlorobenzoic}$ acid under acidic condition is:

Conclusion

The ketone that can be used to produce the given compound is drawn, removing the oxygen next to the carbonyl C which is inserted when it reacts with ${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ and re-forms the C-H bond.

Interpretation Introduction

(c)

Interpretation:

The ketone or aldehyde that can be used to produce the given compound when treated with $\text{m-chlorobenzoic}$ acid under acidic condition is to be drawn.

Concept introduction:

${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ are acids and will react with a ketone or aldehyde in Baeyer-Villiger oxidation. Baeyer–Villiger oxidation produces carboxylic acids from aldehydes, and esters from ketones. In these reactions, a hydrogen or alkyl group departs from the carbonyl carbon, facilitated by the breaking of the weak $\text{O-O}$ bond from peroxyacid $\left({\text{RCO}}_{\text{3}}\text{H}\right)$.

Answer to Problem 21.61P

The ketone that can be used to produce the given compound when it is treated with $\text{m-chlorobenzoic}$ acid under acidic condition is:

Explanation of Solution

The given compound is:

The given compound is an ester that can be produced when a ketone is treated with ${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ in a Baeyer-Villiger oxidation reaction. In a Baeyer-Villiger oxidation reaction, an O atom from the peroxyacid is inserted between the carbonyl C and one of the groups initially bonded to the carbonyl C. To reserve the reaction, remove the oxygen next to the carbonyl C and re-form the C-C bond which is shown in red. The ketone that can be used to produce the given acid compound when it is treated with $\text{m-chlorobenzoic}$ acid under acidic condition is:

Conclusion

The ketone that can be used to produce the given compound is drawn, removing the oxygen next to the carbonyl C which inserted when it react with ${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ and re-forms the C-C bond.

Interpretation Introduction

(d)

Interpretation:

The ketone or aldehyde that can be used to produce the given compound when treated with $\text{m-chlorobenzoic}$ acid under acidic condition is to be drawn.

Concept introduction:

${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ are acids and will react with a ketone or aldehyde in Baeyer-Villiger oxidation. Baeyer–Villiger oxidation produces carboxylic acids from aldehydes, and esters from ketones. In these reactions, a hydrogen or alkyl group departs from the carbonyl carbon, facilitated by the breaking of the weak $\text{O-O}$ bond from peroxyacid $\left({\text{RCO}}_{\text{3}}\text{H}\right)$.

Answer to Problem 21.61P

The ketone that can be used to produce the given compound when it is treated with $\text{m-chlorobenzoic}$ acid under acidic condition is:

Explanation of Solution

The given compound is:

The given compound is an ester that can be produced when a ketone is treated with ${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ in a Baeyer-Villiger oxidation reaction. In a Baeyer-Villiger oxidation reaction, an O atom from the peroxyacid is inserted between the carbonyl C and one of groups initially bonded to the carbonyl C. To reserve the reaction, remove the oxygen next to the carbonyl C and re-form the C-C bond which is shown in red. The ketone that can be used to produce the given acid compound when treated with $\text{m-chlorobenzoic}$ acid under acidic condition is:

Conclusion

The ketone that can be used to produce the given compound is drawn, removing the oxygen next to the carbonyl C which is inserted when it reacts with ${\text{CF}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$ and $\text{MCPBA}$ and re-forms the C-C bond.