The structure of the product formed from acid-catalyzed hydration of ( + ) - α -Pinene should be predicted. Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H 3 O + in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

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Answer 1

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Chapter 10.8, Problem 10E

(a)

Interpretation Introduction

Interpretation: The structure of the product formed from acid-catalyzed hydration of (+)-α-Pinene should be predicted.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

(b)

Interpretation Introduction

Interpretation: The structures of isomeric alcohols with chemical formula C10H18O formed from the treatment of (+)-α-Pinene with aqueous acid should be drawn.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

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5. An unknown hydrocarbon A with the formula C,H12 reacts with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMNO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions and show your reasoning.

Hydrocarbon A, C8H12 absorbs 3 equiv. of hydrogen to give B, C8H18 when hydrogenated over a Pd/C catalyst. Treatment of A with aqueous H2SO4 and Hg(II) gives a single ketone, C. Oxidation of A with KMnO4 gives CO2 and the two carboxylic acids D & E shown below. What would be a structure for A?

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Answer 2

Question

Chapter 10.8, Problem 10E

(a)

Interpretation Introduction

Interpretation: The structure of the product formed from acid-catalyzed hydration of (+)-α-Pinene should be predicted.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

(b)

Interpretation Introduction

Interpretation: The structures of isomeric alcohols with chemical formula C10H18O formed from the treatment of (+)-α-Pinene with aqueous acid should be drawn.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

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Answer 3

Question

Chapter 10.8, Problem 10E

(a)

Interpretation Introduction

Interpretation: The structure of the product formed from acid-catalyzed hydration of (+)-α-Pinene should be predicted.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

(b)

Interpretation Introduction

Interpretation: The structures of isomeric alcohols with chemical formula C10H18O formed from the treatment of (+)-α-Pinene with aqueous acid should be drawn.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

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Answer 4

Question

Chapter 10.8, Problem 10E

(a)

Interpretation Introduction

Interpretation: The structure of the product formed from acid-catalyzed hydration of (+)-α-Pinene should be predicted.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

(b)

Interpretation Introduction

Interpretation: The structures of isomeric alcohols with chemical formula C10H18O formed from the treatment of (+)-α-Pinene with aqueous acid should be drawn.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

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Answer 5

Chapter 10.8, Problem 10E

(a)

Interpretation Introduction

Interpretation: The structure of the product formed from acid-catalyzed hydration of (+)-α-Pinene should be predicted.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

(b)

Interpretation Introduction

Interpretation: The structures of isomeric alcohols with chemical formula C10H18O formed from the treatment of (+)-α-Pinene with aqueous acid should be drawn.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

Answer 6

Chapter 10.8, Problem 10E

(a)

Interpretation Introduction

Interpretation: The structure of the product formed from acid-catalyzed hydration of (+)-α-Pinene should be predicted.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

Answer 7

Chapter 10.8, Problem 10E

(a)

Interpretation Introduction

Interpretation: The structure of the product formed from acid-catalyzed hydration of (+)-α-Pinene should be predicted.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

Answer 8

(b)

Interpretation Introduction

Interpretation: The structures of isomeric alcohols with chemical formula C10H18O formed from the treatment of (+)-α-Pinene with aqueous acid should be drawn.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

Answer 9

(b)

Interpretation Introduction

Interpretation: The structures of isomeric alcohols with chemical formula C10H18O formed from the treatment of (+)-α-Pinene with aqueous acid should be drawn.

Concept introduction: Acid-catalyzed hydration is the electrophilic addition of water. The reactive species that act as a catalyst is H3O+ in the first stage. In the second stage water itself acts as a nucleophile and another water abstracts a proton to give final hydration product as illustrated below.

Answer 10

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Answer 13

Ch. 10.2 - Prob. 1E Ch. 10.2 - Prob. 2E Ch. 10.2 - Prob. 3E Ch. 10.2 - Prob. 4E Ch. 10.2 - Prob. 5E Ch. 10.2 - Prob. 6E Ch. 10.2 - Prob. 7E Ch. 10.2 - Prob. 8E Ch. 10.2 - Prob. 9E Ch. 10.2 - Prob. 10E

Solution Summary: The author illustrates the structure of the product formed from acid-catalyzed hydration.

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