A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found. Concept Introduction : Amides on reduction with lithium aluminum hydride followed by water work-up give the corresponding amines . To find: Draw a structure for the alkaloid halosaline Get the formation of lithium salt by reduction

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Answer 1

Question

Chapter 23, Problem 91CP

(a)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

Amides on reduction with lithium aluminum hydride followed by water work-up give the corresponding amines.

To find: Draw a structure for the alkaloid halosaline

Get the formation of lithium salt by reduction

(b)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

If a compound contains both the azide and lactone ring, lithium aluminum hydride reduces both the groups, azide into the corresponding amine and the lactone ring into the diol groups. LAH is a non-selective reducing agent. For example:

To find: Get the reason for achieving the given transformation in just one step (rather than two) using LAH to reduce both the azide and the amide in one reaction flask

Get the formation of lithium salt by reduction

(c)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

The simple lactone-to-lactam transformation occurs due to the driving force of amine nucleophiles. A nucleophile is a chemical species that donates an electron pair to an electrophile to form a chemical bond in relation to a reaction. All molecules or ions with a free pair of electrons or at least one pi bond can act as nucleophiles.

To find: Provide a mechanism for the lactone-to-lactam ring contraction

Provide the nucleophilic attack in the starting material

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Answer 2

Question

Chapter 23, Problem 91CP

(a)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

Amides on reduction with lithium aluminum hydride followed by water work-up give the corresponding amines.

To find: Draw a structure for the alkaloid halosaline

Get the formation of lithium salt by reduction

(b)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

If a compound contains both the azide and lactone ring, lithium aluminum hydride reduces both the groups, azide into the corresponding amine and the lactone ring into the diol groups. LAH is a non-selective reducing agent. For example:

To find: Get the reason for achieving the given transformation in just one step (rather than two) using LAH to reduce both the azide and the amide in one reaction flask

Get the formation of lithium salt by reduction

(c)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

The simple lactone-to-lactam transformation occurs due to the driving force of amine nucleophiles. A nucleophile is a chemical species that donates an electron pair to an electrophile to form a chemical bond in relation to a reaction. All molecules or ions with a free pair of electrons or at least one pi bond can act as nucleophiles.

To find: Provide a mechanism for the lactone-to-lactam ring contraction

Provide the nucleophilic attack in the starting material

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 23, Problem 91CP

(a)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

Amides on reduction with lithium aluminum hydride followed by water work-up give the corresponding amines.

To find: Draw a structure for the alkaloid halosaline

Get the formation of lithium salt by reduction

(b)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

If a compound contains both the azide and lactone ring, lithium aluminum hydride reduces both the groups, azide into the corresponding amine and the lactone ring into the diol groups. LAH is a non-selective reducing agent. For example:

To find: Get the reason for achieving the given transformation in just one step (rather than two) using LAH to reduce both the azide and the amide in one reaction flask

Get the formation of lithium salt by reduction

(c)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

The simple lactone-to-lactam transformation occurs due to the driving force of amine nucleophiles. A nucleophile is a chemical species that donates an electron pair to an electrophile to form a chemical bond in relation to a reaction. All molecules or ions with a free pair of electrons or at least one pi bond can act as nucleophiles.

To find: Provide a mechanism for the lactone-to-lactam ring contraction

Provide the nucleophilic attack in the starting material

Expert Solution & Answer

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Check out a sample textbook solution

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Answer 4

Question

Chapter 23, Problem 91CP

(a)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

Amides on reduction with lithium aluminum hydride followed by water work-up give the corresponding amines.

To find: Draw a structure for the alkaloid halosaline

Get the formation of lithium salt by reduction

(b)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

If a compound contains both the azide and lactone ring, lithium aluminum hydride reduces both the groups, azide into the corresponding amine and the lactone ring into the diol groups. LAH is a non-selective reducing agent. For example:

To find: Get the reason for achieving the given transformation in just one step (rather than two) using LAH to reduce both the azide and the amide in one reaction flask

Get the formation of lithium salt by reduction

(c)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

The simple lactone-to-lactam transformation occurs due to the driving force of amine nucleophiles. A nucleophile is a chemical species that donates an electron pair to an electrophile to form a chemical bond in relation to a reaction. All molecules or ions with a free pair of electrons or at least one pi bond can act as nucleophiles.

To find: Provide a mechanism for the lactone-to-lactam ring contraction

Provide the nucleophilic attack in the starting material

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 5

Chapter 23, Problem 91CP

(a)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

Amides on reduction with lithium aluminum hydride followed by water work-up give the corresponding amines.

To find: Draw a structure for the alkaloid halosaline

Get the formation of lithium salt by reduction

(b)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

If a compound contains both the azide and lactone ring, lithium aluminum hydride reduces both the groups, azide into the corresponding amine and the lactone ring into the diol groups. LAH is a non-selective reducing agent. For example:

To find: Get the reason for achieving the given transformation in just one step (rather than two) using LAH to reduce both the azide and the amide in one reaction flask

Get the formation of lithium salt by reduction

(c)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

The simple lactone-to-lactam transformation occurs due to the driving force of amine nucleophiles. A nucleophile is a chemical species that donates an electron pair to an electrophile to form a chemical bond in relation to a reaction. All molecules or ions with a free pair of electrons or at least one pi bond can act as nucleophiles.

To find: Provide a mechanism for the lactone-to-lactam ring contraction

Provide the nucleophilic attack in the starting material

Answer 6

Chapter 23, Problem 91CP

(a)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

Amides on reduction with lithium aluminum hydride followed by water work-up give the corresponding amines.

To find: Draw a structure for the alkaloid halosaline

Get the formation of lithium salt by reduction

Answer 7

Chapter 23, Problem 91CP

(a)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

Amides on reduction with lithium aluminum hydride followed by water work-up give the corresponding amines.

To find: Draw a structure for the alkaloid halosaline

Get the formation of lithium salt by reduction

Answer 8

(b)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

If a compound contains both the azide and lactone ring, lithium aluminum hydride reduces both the groups, azide into the corresponding amine and the lactone ring into the diol groups. LAH is a non-selective reducing agent. For example:

To find: Get the reason for achieving the given transformation in just one step (rather than two) using LAH to reduce both the azide and the amide in one reaction flask

Get the formation of lithium salt by reduction

Answer 9

(b)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

If a compound contains both the azide and lactone ring, lithium aluminum hydride reduces both the groups, azide into the corresponding amine and the lactone ring into the diol groups. LAH is a non-selective reducing agent. For example:

To find: Get the reason for achieving the given transformation in just one step (rather than two) using LAH to reduce both the azide and the amide in one reaction flask

Get the formation of lithium salt by reduction

Answer 10

(c)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

The simple lactone-to-lactam transformation occurs due to the driving force of amine nucleophiles. A nucleophile is a chemical species that donates an electron pair to an electrophile to form a chemical bond in relation to a reaction. All molecules or ions with a free pair of electrons or at least one pi bond can act as nucleophiles.

To find: Provide a mechanism for the lactone-to-lactam ring contraction

Provide the nucleophilic attack in the starting material

Answer 11

(c)

Interpretation Introduction

Interpretation: A structure for the alkaloid halosaline, a reason for not getting the product in the given transformation in one step using LAH and a mechanism for the lactone-to-lactam ring contraction have to be found.

Concept Introduction:

The simple lactone-to-lactam transformation occurs due to the driving force of amine nucleophiles. A nucleophile is a chemical species that donates an electron pair to an electrophile to form a chemical bond in relation to a reaction. All molecules or ions with a free pair of electrons or at least one pi bond can act as nucleophiles.

To find: Provide a mechanism for the lactone-to-lactam ring contraction

Provide the nucleophilic attack in the starting material

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 23.2 - Prob. 1LTS Ch. 23.2 - Prob. 1PTS Ch. 23.2 - Prob. 2ATS Ch. 23.2 - Prob. 3ATS Ch. 23.3 - Prob. 4CC Ch. 23.3 - Prob. 5CC Ch. 23.3 - Prob. 6CC Ch. 23.3 - Prob. 7CC Ch. 23.3 - Prob. 8CC Ch. 23.3 - Prob. 9CC

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Chapter 23 Solutions