The intermediate in the Pinacol rearrangement that can be stabilized by resonance delocalization has to be identified. Concept Introduction: Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows, Step 1: Add proton (protonation of Pinacol using acid catalyst). Step 2: Break a bond to give a stable molecules or ions (formation of carbocation). Step 3: 1, 2-shift (migration of substituent from α- to β- carbon). Step 4: deprotonation occurs (take a proton away).

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Answer 1

Question

Chapter 10.7, Problem BQ

Interpretation Introduction

Interpretation:

The intermediate in the Pinacol rearrangement that can be stabilized by resonance delocalization has to be identified.

Concept Introduction:

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

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Answer 2

Question

Chapter 10.7, Problem BQ

Interpretation Introduction

Interpretation:

The intermediate in the Pinacol rearrangement that can be stabilized by resonance delocalization has to be identified.

Concept Introduction:

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

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Check out a sample textbook solution

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Answer 3

Question

Chapter 10.7, Problem BQ

Interpretation Introduction

Interpretation:

The intermediate in the Pinacol rearrangement that can be stabilized by resonance delocalization has to be identified.

Concept Introduction:

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

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Answer 4

Question

Chapter 10.7, Problem BQ

Interpretation Introduction

Interpretation:

The intermediate in the Pinacol rearrangement that can be stabilized by resonance delocalization has to be identified.

Concept Introduction:

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

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Answer 5

Chapter 10.7, Problem BQ

Interpretation Introduction

Interpretation:

The intermediate in the Pinacol rearrangement that can be stabilized by resonance delocalization has to be identified.

Concept Introduction:

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 6

Chapter 10.7, Problem BQ

Interpretation Introduction

Interpretation:

The intermediate in the Pinacol rearrangement that can be stabilized by resonance delocalization has to be identified.

Concept Introduction:

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 7

Chapter 10.7, Problem BQ

Interpretation Introduction

Interpretation:

The intermediate in the Pinacol rearrangement that can be stabilized by resonance delocalization has to be identified.

Concept Introduction:

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 10.1 - Write IUPAC names for these alcohols and include...Ch. 10.1 - Classify each alcohol as primary, secondary, or...Ch. 10.1 - Write IUPAC names for these unsaturated alcohols.Ch. 10.2 - Arrange these compounds in order of increasing...Ch. 10.2 - Prob. 10.5P Ch. 10.4 - Predict the position of equilibrium for this...Ch. 10.5 - Show how to convert (R)-2-pentanol to...Ch. 10.6 - Draw structural formulas for the alkenes formed by...Ch. 10.6 - Propose a mechanism to account for this...Ch. 10.7 - Propose a mechanism to account for the following...

Solution Summary: The author explains that the intermediate in the Pinacol rearrangement that can be stabilized by resonance delocalization has to be identified.

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