a) Interpretation: The product formed in the addition reaction of butanal along with the mechanism of its formation is to be predicted. Concept introduction: Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate. To identify: The product formed in the addition reaction of butanal along with the mechanism of its formation.

Question

Explain the types of electromeric effects +E and -E.

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product formed in the addition reaction of butanal along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of butanal along with the mechanism of its formation.

Interpretation Introduction

b)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of cyclobutanone along with the mechanism of its formation.

Interpretation Introduction

c)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

The reaction given is a mixed aldol reaction. Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Interpretation Introduction

d)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

In intramolecular aldol reactions dicarbonyl compounds such as diketones react with a base to yield a cyclic keto alcohol as the products. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

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Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product formed in the addition reaction of butanal along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of butanal along with the mechanism of its formation.

Interpretation Introduction

b)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of cyclobutanone along with the mechanism of its formation.

Interpretation Introduction

c)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

The reaction given is a mixed aldol reaction. Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Interpretation Introduction

d)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

In intramolecular aldol reactions dicarbonyl compounds such as diketones react with a base to yield a cyclic keto alcohol as the products. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Expert Solution & Answer

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product formed in the addition reaction of butanal along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of butanal along with the mechanism of its formation.

Interpretation Introduction

b)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of cyclobutanone along with the mechanism of its formation.

Interpretation Introduction

c)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

The reaction given is a mixed aldol reaction. Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Interpretation Introduction

d)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

In intramolecular aldol reactions dicarbonyl compounds such as diketones react with a base to yield a cyclic keto alcohol as the products. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product formed in the addition reaction of butanal along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of butanal along with the mechanism of its formation.

Interpretation Introduction

b)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of cyclobutanone along with the mechanism of its formation.

Interpretation Introduction

c)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

The reaction given is a mixed aldol reaction. Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Interpretation Introduction

d)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

In intramolecular aldol reactions dicarbonyl compounds such as diketones react with a base to yield a cyclic keto alcohol as the products. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Expert Solution & Answer

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Answer 5

Chapter 23.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product formed in the addition reaction of butanal along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of butanal along with the mechanism of its formation.

Interpretation Introduction

b)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of cyclobutanone along with the mechanism of its formation.

Interpretation Introduction

c)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

The reaction given is a mixed aldol reaction. Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Interpretation Introduction

d)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

In intramolecular aldol reactions dicarbonyl compounds such as diketones react with a base to yield a cyclic keto alcohol as the products. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Answer 6

Chapter 23.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product formed in the addition reaction of butanal along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of butanal along with the mechanism of its formation.

Answer 7

Chapter 23.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product formed in the addition reaction of butanal along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of butanal along with the mechanism of its formation.

Answer 8

Interpretation Introduction

b)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of cyclobutanone along with the mechanism of its formation.

Answer 9

Interpretation Introduction

b)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction of cyclobutanone along with the mechanism of its formation.

Answer 10

Interpretation Introduction

c)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

The reaction given is a mixed aldol reaction. Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Answer 11

Interpretation Introduction

c)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

The reaction given is a mixed aldol reaction. Aldehydes and ketones that have α- hydrogen atom undergo aldol condensation to yield a β- hydroxyl aldehyde or ketone as the product. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Answer 12

Interpretation Introduction

d)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

In intramolecular aldol reactions dicarbonyl compounds such as diketones react with a base to yield a cyclic keto alcohol as the products. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Answer 13

Interpretation Introduction

d)

Interpretation:

The product formed in the addition reaction given along with the mechanism of its formation is to be predicted.

Concept introduction:

In intramolecular aldol reactions dicarbonyl compounds such as diketones react with a base to yield a cyclic keto alcohol as the products. The reaction occurs in three steps i) Abstraction of α- hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon of the another molecule iii) Protonation of the alkoxide intermediate.

To identify:

The product formed in the addition reaction given along with the mechanism of its formation.

Answer 14

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Answer 25

Ch. 23.1 - Prob. 1P Ch. 23.1 - Prob. 2P Ch. 23.3 - Prob. 3P Ch. 23.3 - Prob. 4P Ch. 23.4 - Prob. 5P Ch. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7P Ch. 23.5 - Prob. 8P Ch. 23.6 - Prob. 9P Ch. 23.6 - What product would you Expect to obtain from base...

Solution Summary: The author explains that the product formed in the addition reaction of butanal along with the mechanism of its formation is to be predicted.

Chapter 23 Solutions