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

For each reaction shown below follow the curved arrows to complete each equationby showing the structure of the products. Identify the acid, the base, the conjugated acid andconjugated base. Consutl the pKa table and choose the direciton theequilibrium goes. However show the curved arrows. Please explain if possible.

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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For each reaction shown below follow the curved arrows to complete each equationby showing the structure of the products. Identify the acid, the base, the conjugated acid andconjugated base. Consutl the pKa table and choose the direciton theequilibrium goes. However show the curved arrows. Please explain if possible.

A molecule shows peaks at 1379, 1327, 1249, 739 cm-1. Draw a diagram of the energy levels for such a molecule. Draw arrows for the possible transitions that could occur for the molecule. In the diagram imagine exciting an electron, what are its various options for getting back to the ground state? What process would promote radiation less decay? What do you expect for the lifetime of an electron in the T1 state? Why is phosphorescence emission weak in most substances? What could you do to a sample to enhance the likelihood that phosphorescence would occur over radiationless decay?

Rank the indicated C—C bonds in increasing order of bond length. Explain as why to the difference.

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.

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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.

Expert Solution & Answer

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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