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

Question

Want to see the full answer?

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

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

H HgSO4, H2O H2SO4

12. Choose the best diene and dienophile pair that would react the fastest. CN CN CO₂Et -CO₂Et .CO₂Et H3CO CO₂Et A B C D E F

(6 pts - 2 pts each part) Although we focused our discussion on hydrogen light emission, all elements have distinctive emission spectra. Sodium (Na) is famous for its spectrum being dominated by two yellow emission lines at 589.0 and 589.6 nm, respectively. These lines result from electrons relaxing to the 3s subshell. a. What is the photon energy (in J) for one of these emission lines? Show your work. b. To what electronic transition in hydrogen is this photon energy closest to? Justify your answer-you shouldn't need to do numerical calculations. c. Consider the 3s subshell energy for Na - use 0 eV as the reference point for n=∞. What is the energy of the subshell that the electron relaxes from? Choose the same emission line that you did for part (a) and show your work.

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

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

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

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Want to see the full answer?

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

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Want to see the full answer?

Chapter 22 Solutions