a) Interpretation: Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not is to be stated. A mechanism to explain the formation of the ketone is to be proposed. Concept introduction: The decarboxylation of a Î²- keto acid takes place through the formation of a planar enol intermediate which then tautomerizes to the keto form. If the Î²- keto acid is optically active and if the chiral centre is involved in the reaction, the ketone product will be racemic and optically inactive. If the chiral centre is not involved in the reaction then the optical activity is retained in the ketone product. To state: Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not. To propose: A mechanism to explain the formation of the ketone.

Question

b) Esters can undergo hydrolysis to give an alcohol and a carboxylic acid. Lactone P which is a cyclic ester, can undergo base-catalyzed hydrolysis to give a hydroxy carboxylic acid. Write the plausible mechanism for the transformation.

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not is to be stated. A mechanism to explain the formation of the ketone is to be proposed.

Concept introduction:

The decarboxylation of a Î²- keto acid takes place through the formation of a planar enol intermediate which then tautomerizes to the keto form. If the Î²- keto acid is optically active and if the chiral centre is involved in the reaction, the ketone product will be racemic and optically inactive. If the chiral centre is not involved in the reaction then the optical activity is retained in the ketone product.

To state:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not.

To propose:

A mechanism to explain the formation of the ketone.

Interpretation Introduction

b)

Interpretation:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not is to be stated. A mechanism to explain the formation of the ketone is to be proposed.

Concept introduction:

The decarboxylation of a Î²- keto acid takes place through the formation of a planar enol intermediate which then tautomerizes to the keto form. If the Î²- keto acid is optically active and if the chiral centre is involved in the reaction, the ketone product will be racemic and optically inactive. If the chiral centre is not involved in the reaction then the optical activity is retained in the ketone product.

To state:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not.

To propose:

A mechanism to explain the formation of the ketone.

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b) Esters can undergo hydrolysis to give an alcohol and a carboxylic acid. Lactone P which is a cyclic ester, can undergo base-catalyzed hydrolysis to give a hydroxy carboxylic acid. Write the plausible mechanism for the transformation.

Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed tosynthesize the drug?

A ketone undergoes acid-catalyzed bromination, acid-catalyzed chlorination, racemization, and acid-catalyzed deuterium exchange at the α-carbon. All of these reactions have similar rate constants. What does this tell you about the mechanisms of these reactions?

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not is to be stated. A mechanism to explain the formation of the ketone is to be proposed.

Concept introduction:

The decarboxylation of a Î²- keto acid takes place through the formation of a planar enol intermediate which then tautomerizes to the keto form. If the Î²- keto acid is optically active and if the chiral centre is involved in the reaction, the ketone product will be racemic and optically inactive. If the chiral centre is not involved in the reaction then the optical activity is retained in the ketone product.

To state:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not.

To propose:

A mechanism to explain the formation of the ketone.

Interpretation Introduction

b)

Interpretation:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not is to be stated. A mechanism to explain the formation of the ketone is to be proposed.

Concept introduction:

The decarboxylation of a Î²- keto acid takes place through the formation of a planar enol intermediate which then tautomerizes to the keto form. If the Î²- keto acid is optically active and if the chiral centre is involved in the reaction, the ketone product will be racemic and optically inactive. If the chiral centre is not involved in the reaction then the optical activity is retained in the ketone product.

To state:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not.

To propose:

A mechanism to explain the formation of the ketone.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not is to be stated. A mechanism to explain the formation of the ketone is to be proposed.

Concept introduction:

The decarboxylation of a Î²- keto acid takes place through the formation of a planar enol intermediate which then tautomerizes to the keto form. If the Î²- keto acid is optically active and if the chiral centre is involved in the reaction, the ketone product will be racemic and optically inactive. If the chiral centre is not involved in the reaction then the optical activity is retained in the ketone product.

To state:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not.

To propose:

A mechanism to explain the formation of the ketone.

Interpretation Introduction

b)

Interpretation:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not is to be stated. A mechanism to explain the formation of the ketone is to be proposed.

Concept introduction:

The decarboxylation of a Î²- keto acid takes place through the formation of a planar enol intermediate which then tautomerizes to the keto form. If the Î²- keto acid is optically active and if the chiral centre is involved in the reaction, the ketone product will be racemic and optically inactive. If the chiral centre is not involved in the reaction then the optical activity is retained in the ketone product.

To state:

Whether the ketone obtained by the decarboxylation of the optically active Î²- keto acid will be optically active or not.

To propose:

A mechanism to explain the formation of the ketone.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.SE, Problem 23MP

Interpretation Introduction