a) Interpretation: Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given. Concept introduction: Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other. To state: Whether the compound shown can be prepared by a mixed aldol reaction. To give: The reactants from which it can be prepared.

Question

2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O H

Answer 1

Question

Chapter 23.5, Problem 8P

Interpretation Introduction

a)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Interpretation Introduction

b)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Interpretation Introduction

c)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

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2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O H

What are the products of an aldol cyclization for the following compound?

Provide the necessary reagents for the following transformation. Ph Me Ph Et

Answer 2

Question

Chapter 23.5, Problem 8P

Interpretation Introduction

a)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Interpretation Introduction

b)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Interpretation Introduction

c)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Expert Solution & Answer

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Answer 3

Question

Chapter 23.5, Problem 8P

Interpretation Introduction

a)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Interpretation Introduction

b)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Interpretation Introduction

c)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Expert Solution & Answer

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Answer 4

Question

Chapter 23.5, Problem 8P

Interpretation Introduction

a)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Interpretation Introduction

b)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Interpretation Introduction

c)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Expert Solution & Answer

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Answer 5

Chapter 23.5, Problem 8P

Interpretation Introduction

a)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Interpretation Introduction

b)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Interpretation Introduction

c)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Answer 6

Chapter 23.5, Problem 8P

Interpretation Introduction

a)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Answer 7

Chapter 23.5, Problem 8P

Interpretation Introduction

a)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Answer 8

Interpretation Introduction

b)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Answer 9

Interpretation Introduction

b)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Answer 10

Interpretation Introduction

c)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Answer 11

Interpretation Introduction

c)

Interpretation:

Whether the compound shown can be prepared by a mixed aldol reaction is to be stated. Further the reactants from which it can be prepared are to be given.

Concept introduction:

Mixed aldol condensation leads to a single product if i) one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To state:

Whether the compound shown can be prepared by a mixed aldol reaction.

To give:

The reactants from which it can be prepared.

Answer 12

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Answer 23

Ch. 23.1 - Prob. 1P Ch. 23.1 - Prob. 2P Ch. 23.3 - Prob. 3P Ch. 23.3 - Prob. 4P Ch. 23.4 - Prob. 5P Ch. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7P Ch. 23.5 - Prob. 8P Ch. 23.6 - Prob. 9P Ch. 23.6 - What product would you Expect to obtain from base...

Solution Summary: The author states that the compound can be prepared by a mixed aldol reaction between benzaldehyde and acetone.

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Chapter 23 Solutions