The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

Question

What would be the reagents and conditions above and below the arrow that will complete the proposed acetoacetic ester synthesis? If it cannot be done efficiently, then I will choose that answer. There could be 2 or 4 reagents involved. Please provide a detailed explanation and drawings showing how it would proceed with the correct reagents.

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 21, Problem 21.62P

(a)

Interpretation Introduction

Interpretation:

The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

(b)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of A to B.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

(c)

Interpretation Introduction

Interpretation:

The mechanism for the conversion of B to C is to be explained.

Concept introduction:

Wittig Reaction: It is an organic reaction where an aldehyde or a ketone gets converted to epoxide by replacing carbonyl group. A sulfur ylide is used for this conversion. It is a neutral molecule where positively charged sulfur is attached to a negatively charged carbon atom.

(d)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of C to D.

Concept introduction:

Amines reaction with epoxide gives ring opening product.

(e)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of D to albuterol.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

(f)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Chiral:

A molecule is non superimposable on its mirror image is called chiral molecule. Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

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What would be the reagents and conditions above and below the arrow that will complete the proposed acetoacetic ester synthesis? If it cannot be done efficiently, then I will choose that answer. There could be 2 or 4 reagents involved. Please provide a detailed explanation and drawings showing how it would proceed with the correct reagents.

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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 21, Problem 21.62P

(a)

Interpretation Introduction

Interpretation:

The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

(b)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of A to B.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

(c)

Interpretation Introduction

Interpretation:

The mechanism for the conversion of B to C is to be explained.

Concept introduction:

Wittig Reaction: It is an organic reaction where an aldehyde or a ketone gets converted to epoxide by replacing carbonyl group. A sulfur ylide is used for this conversion. It is a neutral molecule where positively charged sulfur is attached to a negatively charged carbon atom.

(d)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of C to D.

Concept introduction:

Amines reaction with epoxide gives ring opening product.

(e)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of D to albuterol.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

(f)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Chiral:

A molecule is non superimposable on its mirror image is called chiral molecule. Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

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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 21, Problem 21.62P

(a)

Interpretation Introduction

Interpretation:

The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

(b)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of A to B.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

(c)

Interpretation Introduction

Interpretation:

The mechanism for the conversion of B to C is to be explained.

Concept introduction:

Wittig Reaction: It is an organic reaction where an aldehyde or a ketone gets converted to epoxide by replacing carbonyl group. A sulfur ylide is used for this conversion. It is a neutral molecule where positively charged sulfur is attached to a negatively charged carbon atom.

(d)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of C to D.

Concept introduction:

Amines reaction with epoxide gives ring opening product.

(e)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of D to albuterol.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

(f)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Chiral:

A molecule is non superimposable on its mirror image is called chiral molecule. Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

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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 21, Problem 21.62P

(a)

Interpretation Introduction

Interpretation:

The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

(b)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of A to B.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

(c)

Interpretation Introduction

Interpretation:

The mechanism for the conversion of B to C is to be explained.

Concept introduction:

Wittig Reaction: It is an organic reaction where an aldehyde or a ketone gets converted to epoxide by replacing carbonyl group. A sulfur ylide is used for this conversion. It is a neutral molecule where positively charged sulfur is attached to a negatively charged carbon atom.

(d)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of C to D.

Concept introduction:

Amines reaction with epoxide gives ring opening product.

(e)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of D to albuterol.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

(f)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Chiral:

A molecule is non superimposable on its mirror image is called chiral molecule. Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

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Answer 5

Chapter 21, Problem 21.62P

(a)

Interpretation Introduction

Interpretation:

The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

(b)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of A to B.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

(c)

Interpretation Introduction

Interpretation:

The mechanism for the conversion of B to C is to be explained.

Concept introduction:

Wittig Reaction: It is an organic reaction where an aldehyde or a ketone gets converted to epoxide by replacing carbonyl group. A sulfur ylide is used for this conversion. It is a neutral molecule where positively charged sulfur is attached to a negatively charged carbon atom.

(d)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of C to D.

Concept introduction:

Amines reaction with epoxide gives ring opening product.

(e)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of D to albuterol.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

(f)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Chiral:

A molecule is non superimposable on its mirror image is called chiral molecule. Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Answer 6

Chapter 21, Problem 21.62P

(a)

Interpretation Introduction

Interpretation:

The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

Answer 7

Chapter 21, Problem 21.62P

(a)

Interpretation Introduction

Interpretation:

The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of A to B.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of A to B.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The mechanism for the conversion of B to C is to be explained.

Concept introduction:

Wittig Reaction: It is an organic reaction where an aldehyde or a ketone gets converted to epoxide by replacing carbonyl group. A sulfur ylide is used for this conversion. It is a neutral molecule where positively charged sulfur is attached to a negatively charged carbon atom.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The mechanism for the conversion of B to C is to be explained.

Concept introduction:

Wittig Reaction: It is an organic reaction where an aldehyde or a ketone gets converted to epoxide by replacing carbonyl group. A sulfur ylide is used for this conversion. It is a neutral molecule where positively charged sulfur is attached to a negatively charged carbon atom.

Answer 12

(d)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of C to D.

Concept introduction:

Amines reaction with epoxide gives ring opening product.

Answer 13

(d)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of C to D.

Concept introduction:

Amines reaction with epoxide gives ring opening product.

Answer 14

(e)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of D to albuterol.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

Answer 15

(e)

Interpretation Introduction

Interpretation:

The reagent and experiment condition is to be given for the conversion of D to albuterol.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

Answer 16

(f)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Chiral:

A molecule is non superimposable on its mirror image is called chiral molecule. Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Answer 17

(f)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Chiral:

A molecule is non superimposable on its mirror image is called chiral molecule. Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Answer 18

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Ch. 21.2 - Construct a Frost circle for a planar...Ch. 21.2 - Which compound gives a signal in the 1H-NMR...Ch. 21.2 - Prob. 21.3P Ch. 21.2 - Prob. 21.4P Ch. 21.3 - Prob. 21.5P Ch. 21.4 - Arrange these compounds in order of increasing...Ch. 21.4 - Prob. AQ Ch. 21.4 - Prob. BQ Ch. 21.4 - Prob. CQ Ch. 21.5 - Prob. 21.7P

The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

Interpretation: The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

Interpretation: The reagent and experiment condition is to be given for the conversion of A to B. Concept introduction: Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

Interpretation: The reagent and experiment condition is to be given for the conversion of C to D. Concept introduction: Amines reaction with epoxide gives ring opening product.

Interpretation: The reagent and experiment condition is to be given for the conversion of D to albuterol. Concept introduction: Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

Chapter 21 Solutions

Interpretation:

The mechanism of 4-Hydroxybenzaldehyde to compound A has to be shown.

Interpretation:

The reagent and experiment condition is to be given for the conversion of A to B.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.

Interpretation:

The reagent and experiment condition is to be given for the conversion of C to D.

Concept introduction:

Amines reaction with epoxide gives ring opening product.

Interpretation:

The reagent and experiment condition is to be given for the conversion of D to albuterol.

Concept introduction:

Diol is to protect the ketone and aldehyde (carbonyl group). In this reaction acetone is protected as acetal by using ethylene glycol.