To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of 2,6-heptanedione Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones . Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide. One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β -hydroxy aldehyde if two aldehydes combine and β -hydroxy ketone if two ketones combine. If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

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Answer 1

Question

Chapter 17.15, Problem 33P

(a)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,6-heptanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

(b)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,8-nonanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

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a. Write the structure for the β-hydroxycarbonyl compound and their dehydration product formed by aldol condensation of (a) butanal (b) cyclohexanone. b. Can 3,3-dimethyl-2-butanone be synthesized from acetoacetic ester? Explain.

Grignard reagents react with oxirane (ethylene oxide) to form 1° alcohols but can be prepared in tetrahydrofuran solvent. Why is this difference in behavior observed? A. There is a better leaving group in the oxirane molecule. B. Steric hindrance in the case of tetrahydrofuran precludes reaction with the Grignard. C. It is easier to obtain tetrahydrofuran in anhydrous condition. D. Oxirane is a cyclic ether, while tetrahydrofuran is a hydrocarbon. E. The oxirane ring is the more highly strained.

In the Friedel-Crafts alkylation of benzene, dialkylation is often a significant by-product. In the Friedel-Crafts acylation of benzene, diacylation is not a significant by-product. Which of the following is the primary reason for this difference? a. Acyl cations are more difficult to make with Lewis acids b.Unlike acyl cations, carbocations can undergo rearrangements. c.Alkyl groups activate the ring to further substitution, acyl groups deactivate it. d. Alkyl groups activate the ring to further substitution, acyl groups deactivate it

Answer 2

Question

Chapter 17.15, Problem 33P

(a)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,6-heptanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

(b)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,8-nonanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

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Answer 3

Question

Chapter 17.15, Problem 33P

(a)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,6-heptanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

(b)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,8-nonanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

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Answer 4

Question

Chapter 17.15, Problem 33P

(a)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,6-heptanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

(b)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,8-nonanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

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Check out a sample textbook solution

See solution

Answer 5

Chapter 17.15, Problem 33P

(a)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,6-heptanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

(b)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,8-nonanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

Answer 6

Chapter 17.15, Problem 33P

(a)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,6-heptanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

Answer 7

Chapter 17.15, Problem 33P

(a)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,6-heptanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

Answer 8

(b)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,8-nonanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

Answer 9

(b)

Interpretation Introduction

Interpretation: To prepare the cyclic product other than six-membered rings from intramolecular aldol addition of

2,8-nonanedione

Concept introduction: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

If a compound has two functional groups that can react with each other, an intramolecular reaction readily occurs if the reaction leads to occur five or six-membered rings.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 17.1 - Prob. 1P Ch. 17.1 - Prob. 2P Ch. 17.1 - Prob. 3P Ch. 17.1 - Prob. 4P Ch. 17.1 - Rank the compounds in each of the following groups...Ch. 17.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 17.3 - Draw the enol tautomers for each of the following...Ch. 17.3 - Prob. 8P Ch. 17.4 - Prob. 9P Ch. 17.4 - Prob. 10P

Solution Summary: The author explains that aldol reaction is an addition reaction of aldehydes and ketones.

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Chapter 17 Solutions