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

Question

Want to see the full answer?

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

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Identifying electron-donating and For each of the substituted benzene molecules below, determine the inductive and resonance effects the substituent will have on the benzene ring, as well as the overall electron-density of the ring compared to unsubstituted benzene. Molecule Inductive Effects NH2 ○ donating NO2 Explanation Check withdrawing no inductive effects Resonance Effects Overall Electron-Density ○ donating O withdrawing O no resonance effects O donating O withdrawing O donating withdrawing O no inductive effects Ono resonance effects O electron-rich electron-deficient O similar to benzene O electron-rich O electron-deficient O similar to benzene olo 18 Ar 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility

Rank each of the following substituted benzene molecules in order of which will react fastest (1) to slowest (4) by electrophilic aromatic substitution. Explanation Check Х (Choose one) OH (Choose one) OCH3 (Choose one) OH (Choose one) © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center

Assign R or S to all the chiral centers in each compound drawn below porat bg 9 Br Br

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

Want to see the full answer?

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

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Want to see the full answer?

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

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. 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

Want to see the full answer?

Chapter 23 Solutions