(a) Interpretation: A stepwise mechanism for the given reaction is to be drawn. Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

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Answer 1

Question

Chapter 9, Problem 9.81P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the given reaction is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

Interpretation Introduction

(b)

Interpretation: The rearrangement product formed from diol D is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

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1,2-Diols are converted to carbonyl compounds when treated with strong acids, in a reaction called the pinacol rearrangement. (a) Draw a stepwise mechanism for this reaction. (Hint: The reaction proceeds by way of carbocation intermediates.) (b) Assuming that the pinacol rearrangement occurs via the more stable carbocation, draw the rearrangement product formed from diol D.

1) The carbon-oxygen double bond present in aldehydes and ketones is very polar. What does this mean and how does it arise? 2) The carbon-oxygen double bond is readily attacked by nucleophiles like cyanide ions or ammonia. (i) What do you understand by the term nucleophile? (ii) Which part of the carbon-oxygen double bond is attractive to nucleophiles? 3) Why is there a difference between aldehydes and ketones in their response to oxidizing agents such as potassium dichromate(VI) solution acidified with dilute sulfuric acid?

(a) Add curved arrows for each step to show how A is converted to the epoxy ketone C. (b) Classify the conversion of A to C as a substitution, elimination, or addition. (c) Draw one additional resonance structure for B.

Answer 2

Question

Chapter 9, Problem 9.81P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the given reaction is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

Interpretation Introduction

(b)

Interpretation: The rearrangement product formed from diol D is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

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Answer 3

Question

Chapter 9, Problem 9.81P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the given reaction is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

Interpretation Introduction

(b)

Interpretation: The rearrangement product formed from diol D is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

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Answer 4

Question

Chapter 9, Problem 9.81P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the given reaction is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

Interpretation Introduction

(b)

Interpretation: The rearrangement product formed from diol D is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

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Answer 5

Chapter 9, Problem 9.81P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the given reaction is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

Interpretation Introduction

(b)

Interpretation: The rearrangement product formed from diol D is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

Answer 6

Chapter 9, Problem 9.81P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the given reaction is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

Answer 7

Chapter 9, Problem 9.81P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the given reaction is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

Answer 8

Interpretation Introduction

(b)

Interpretation: The rearrangement product formed from diol D is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

Answer 9

Interpretation Introduction

(b)

Interpretation: The rearrangement product formed from diol D is to be drawn.

Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 9 - Draw all constitutional isomers having molecular...Ch. 9 - Prob. 9.2P Ch. 9 - Give the IUPAC name for each compound.Ch. 9 - Problem 9.3 Give the structure corresponding to...Ch. 9 - Prob. 9.5P Ch. 9 - Name CH33COCH3, a gasoline additive commonly...Ch. 9 - Name each epoxide. a. (two ways) b. c. (two...Ch. 9 - Problem 9.6 Rank the following compounds in order...Ch. 9 - Which mechanism is favored by the use of crown...Ch. 9 - Draw the organic product of each reaction.

Solution Summary: The author describes Pinacol rearrangement as an acid catalyzed conversion of 1, 2-diols into carbonyl compounds.

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