The mechanism for the hydrolysis of the given compound under basic conditions is to be drawn, the product that contains 18 O label is to be predicted and also if the product butan-2-ol would be pure ( R ), pure ( S ) or racemized is to be predicted. Concept introduction: Hydrolysis of esters occurs under acidic and basic conditions. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

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Answer 1

Question

Chapter 21.7B, Problem 21.16P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under basic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic conditions. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under acidic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic condition. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

(c)

Interpretation Introduction

Interpretation:

An experimental proof for the position of 18O label in the product is to be explained.

Concept introduction:

The replacement of atom with its isotope in a chemical compound is termed as isotope labelling. The physical and chemical properties of compound change on attachment of isotope to it.

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10. For the following, use ONLY reactions we have studied in class. a) Write out 6 completely different reactions of acetophenone (reagent, product). b) Write out 3 preparations of 2-methyl-2-butanola different starting material for each one. You may use preps where you just change the functional group, and/or preps where you have to construct the carbon chain. c) Write out 3 preparations of pentanoic acid, a different starting material for each one. You may use preps where you just change the functiona group, and/or preps where you have to construct the carbon chain.

For the reduction of 2-methyl cyclohexanone to methyl cyclohexanol using NaBH4... 1. What is the reaction mechanism (draw curved arrows)? What is the nucleophile? Electrophile? 2. Using your reaction mechanism from the above question, sketch the reaction coordinatediagram. What does the transition state most likely look like? What is the rate-determining step?

Complete the mechanism for the reaction of butanone with NaBH, followed by the addition of aqueous acid. 1. NABH4 final product 2. H3O* Step 2: Draw the charged organic intermediate product. Include nonbonding electrons and Step 1: draw curved arrows. Select Draw Rings More Erase charges. Omit the counterion. HB Na o C Select Draw Rings More Erase C H В :0 : H. H, O* H - B Na + ↑

Answer 2

Question

Chapter 21.7B, Problem 21.16P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under basic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic conditions. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under acidic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic condition. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

(c)

Interpretation Introduction

Interpretation:

An experimental proof for the position of 18O label in the product is to be explained.

Concept introduction:

The replacement of atom with its isotope in a chemical compound is termed as isotope labelling. The physical and chemical properties of compound change on attachment of isotope to it.

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Answer 3

Question

Chapter 21.7B, Problem 21.16P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under basic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic conditions. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under acidic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic condition. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

(c)

Interpretation Introduction

Interpretation:

An experimental proof for the position of 18O label in the product is to be explained.

Concept introduction:

The replacement of atom with its isotope in a chemical compound is termed as isotope labelling. The physical and chemical properties of compound change on attachment of isotope to it.

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Answer 4

Question

Chapter 21.7B, Problem 21.16P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under basic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic conditions. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under acidic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic condition. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

(c)

Interpretation Introduction

Interpretation:

An experimental proof for the position of 18O label in the product is to be explained.

Concept introduction:

The replacement of atom with its isotope in a chemical compound is termed as isotope labelling. The physical and chemical properties of compound change on attachment of isotope to it.

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Answer 5

Chapter 21.7B, Problem 21.16P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under basic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic conditions. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under acidic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic condition. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

(c)

Interpretation Introduction

Interpretation:

An experimental proof for the position of 18O label in the product is to be explained.

Concept introduction:

The replacement of atom with its isotope in a chemical compound is termed as isotope labelling. The physical and chemical properties of compound change on attachment of isotope to it.

Answer 6

Chapter 21.7B, Problem 21.16P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under basic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic conditions. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

Answer 7

Chapter 21.7B, Problem 21.16P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under basic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic conditions. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under acidic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic condition. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The mechanism for the hydrolysis of the given compound under acidic conditions is to be drawn, the product that contains 18O label is to be predicted and also if the product butan-2-ol would be pure (R), pure (S) or racemized is to be predicted.

Concept introduction:

Hydrolysis of esters occurs under acidic and basic condition. Carboxylate ion and alcohol are obtained by the hydrolysis of ester under basic condition whereas; carboxylic acid and alcohol are obtained from the hydrolysis of ester under acidic condition.

Answer 10

(c)

Interpretation Introduction

Interpretation:

An experimental proof for the position of 18O label in the product is to be explained.

Concept introduction:

The replacement of atom with its isotope in a chemical compound is termed as isotope labelling. The physical and chemical properties of compound change on attachment of isotope to it.

Answer 11

(c)

Interpretation Introduction

Interpretation:

An experimental proof for the position of 18O label in the product is to be explained.

Concept introduction:

The replacement of atom with its isotope in a chemical compound is termed as isotope labelling. The physical and chemical properties of compound change on attachment of isotope to it.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 21.2F - Name the following carboxylic acid derivatives,...Ch. 21.4A - Prob. 21.2P Ch. 21.4A - Prob. 21.3P Ch. 21.4A - Prob. 21.4P Ch. 21.5C - Prob. 21.7P Ch. 21.6 - When ethyl 4-hydroxybutyrate is heated in the...Ch. 21.6 - Propose a mechanism for the following ring-opening...Ch. 21.6 - Prob. 21.15P Ch. 21.7B - Prob. 21.16P Ch. 21.7C - Prob. 21.19P

Solution Summary: The author explains the mechanism for hydrolysis of esters under acidic and basic conditions. Hydroxide ion attacks the carbonyl carbon to form an intermediate.

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Chapter 21 Solutions