The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions. Concept Introduction : An azide is converted into an amine through hydrogenation in the presence of platinum or palladium. To find: Draw the structures of 2 and 3 Do hydrogenation on an azide

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Answer 1

Question

Chapter 22, Problem 97CP

(a)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An azide is converted into an amine through hydrogenation in the presence of platinum or palladium.

To find: Draw the structures of 2 and 3

Do hydrogenation on an azide

(b)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Provide an acid-catalyzed mechanism for the conversion of 3 to 4

Do protonation for imine

(c)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Get the reasons for the equilibrium favor enamine 4 over imine 3

Explain the conjugation

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Answer 2

Question

Chapter 22, Problem 97CP

(a)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An azide is converted into an amine through hydrogenation in the presence of platinum or palladium.

To find: Draw the structures of 2 and 3

Do hydrogenation on an azide

(b)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Provide an acid-catalyzed mechanism for the conversion of 3 to 4

Do protonation for imine

(c)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Get the reasons for the equilibrium favor enamine 4 over imine 3

Explain the conjugation

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See solution

Answer 3

Question

Chapter 22, Problem 97CP

(a)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An azide is converted into an amine through hydrogenation in the presence of platinum or palladium.

To find: Draw the structures of 2 and 3

Do hydrogenation on an azide

(b)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Provide an acid-catalyzed mechanism for the conversion of 3 to 4

Do protonation for imine

(c)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Get the reasons for the equilibrium favor enamine 4 over imine 3

Explain the conjugation

Expert Solution & Answer

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Answer 4

Question

Chapter 22, Problem 97CP

(a)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An azide is converted into an amine through hydrogenation in the presence of platinum or palladium.

To find: Draw the structures of 2 and 3

Do hydrogenation on an azide

(b)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Provide an acid-catalyzed mechanism for the conversion of 3 to 4

Do protonation for imine

(c)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Get the reasons for the equilibrium favor enamine 4 over imine 3

Explain the conjugation

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 5

Chapter 22, Problem 97CP

(a)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An azide is converted into an amine through hydrogenation in the presence of platinum or palladium.

To find: Draw the structures of 2 and 3

Do hydrogenation on an azide

(b)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Provide an acid-catalyzed mechanism for the conversion of 3 to 4

Do protonation for imine

(c)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Get the reasons for the equilibrium favor enamine 4 over imine 3

Explain the conjugation

Answer 6

Chapter 22, Problem 97CP

(a)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An azide is converted into an amine through hydrogenation in the presence of platinum or palladium.

To find: Draw the structures of 2 and 3

Do hydrogenation on an azide

Answer 7

Chapter 22, Problem 97CP

(a)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An azide is converted into an amine through hydrogenation in the presence of platinum or palladium.

To find: Draw the structures of 2 and 3

Do hydrogenation on an azide

Answer 8

(b)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Provide an acid-catalyzed mechanism for the conversion of 3 to 4

Do protonation for imine

Answer 9

(b)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Provide an acid-catalyzed mechanism for the conversion of 3 to 4

Do protonation for imine

Answer 10

(c)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Get the reasons for the equilibrium favor enamine 4 over imine 3

Explain the conjugation

Answer 11

(c)

Interpretation Introduction

Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.

Concept Introduction:

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H₂O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.

To find: Get the reasons for the equilibrium favor enamine 4 over imine 3

Explain the conjugation

Answer 12

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Answer 13

Expert Solution & Answer

Answer 14

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Answer 15

Ch. 22.2 - Prob. 1LTS Ch. 22.2 - Prob. 1PTS Ch. 22.2 - Prob. 2PTS Ch. 22.2 - Prob. 3ATS Ch. 22.3 - Prob. 4CC Ch. 22.3 - Prob. 5CC Ch. 22.3 - Prob. 6CC Ch. 22.3 - Prob. 7CC Ch. 22.3 - Prob. 8CC Ch. 22.3 - Prob. 9CC

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Chapter 22 Solutions