(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.

Question

Want to see the full answer?

Answer 1

Question

Chapter 9, Problem 9.79P

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Determine if CH3CH2ONa is a suitable reagent to deprotonate the following compound. Explain why. Draw the complete reaction, including the curved arrow mechanism.

(a) What is the major alkene formed when A is dehydrated with HS2O4? (b) What is the major alkene formed when A is treated with POCl3 and pyridine? Explain why the major product is different in these reactions.

1,2-Diols are converted to carbonyl compounds when treated with strongacids, in a reaction called the pinacol rearrangement. (a) Draw a stepwisemechanism for this reaction. (Hint: The reaction proceeds by way ofcarbocation intermediates.) (b) Assuming that the pinacol rearrangementoccurs via the more stable carbocation, draw the rearrangement productformed from diol D.

Answer 2

Question

Chapter 9, Problem 9.79P

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 9, Problem 9.79P

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 9, Problem 9.79P

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 9, Problem 9.79P

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 9.79P

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 9.79P

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

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 13

Ch. 9 - Problem 9.1 Label each ether and alcohol in...Ch. 9 - Give the IUPAC name for each compound.Ch. 9 - Problem 9.3 Give the structure corresponding to...Ch. 9 - Name each of the following ethers.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 - Problem 9.8 Draw the organic product of each...Ch. 9 - Prob. 9.9P Ch. 9 - Problem 9.10 Draw the products of each reaction. ...

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

Concept explainers

Want to see the full answer?

Chapter 9 Solutions