Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β − k e t o a c i d Concept introduction: Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below, If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation . Simple carboxylic acids do not decarboxylate readily. Decarboxylation of β − k e t o a c i d is shown below, The mechanism of thermal decarboxylation involves two processes, (i) Redistribution of electrons in a cyclic transition state. (ii) Cyclic transition state possesses keto-enol tautomerism.

Question

Acetone reacts with carbohydrates in the presence of an acid catalyst to form products that are commonly referred to as “isopropylidene” or “acetonide” derivatives. The carbohydrate d-ribono-(1,4)-lactone reacts with acetone in the presence of hydrochloric acid to give the acetonide shown here. Write a mechanism for this reaction.

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 17, Problem 17.41P

(a)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

The mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

(b)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

Simply the mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

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Acetone reacts with carbohydrates in the presence of an acid catalyst to form products that are commonly referred to as “isopropylidene” or “acetonide” derivatives. The carbohydrate d-ribono-(1,4)-lactone reacts with acetone in the presence of hydrochloric acid to give the acetonide shown here. Write a mechanism for this reaction.

Upon hydration of 2-heptyne in the presence of HgSO4 and H2SO4, the two carbons of the triple bond are similarly but not identically substituted resulting in two regioisomeric enols, each of which gives a different ketone. Supply the names of the two enols formed.

Please show the mechanism for the reagents p-nitrobenzyl ester AND p-Bromophenacyl ester. The unknwon in question is 3-Bromobenzoic Acid.

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 17, Problem 17.41P

(a)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

The mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

(b)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

Simply the mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

Expert Solution & Answer

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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 17, Problem 17.41P

(a)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

The mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

(b)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

Simply the mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

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 17, Problem 17.41P

(a)

Interpretation Introduction