The structure of a ketone formed in 73% yield in the pinacol re-arrangement which proceeds by the way of more stable of the two carbocations formed of the given vicinal diol is to be chosen. Concept Introduction: During pinacol re-arrangement, a diol is converted to a ketone. The reaction begins by protonation of one of the hydroxyl groups. The loss of hydroxyl group produces initial carbocation. The initial carbocation results in the most stable carbocation. In the next step, the water molecule departs, and an alkyl group from the adjacent carbon atom migrates to its position. A new carbocation is created, where the hydroxyl group is attached to the carbon bearing the positive charge. The unshared electrons pair on this hydroxyl group stabilizes the carbocation. The final step is the formation of a carbonyl group and abstraction of a proton from the oxygen atom.

Question

Want to see the full answer?

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 16, Problem 46DSP

Interpretation Introduction

Interpretation:

The structure of a ketone formed in 73% yield in the pinacol re-arrangement which proceeds by the way of more stable of the two carbocations formed of the given vicinal diol is to be chosen.

Concept Introduction:

During pinacol re-arrangement, a diol is converted to a ketone.

The reaction begins by protonation of one of the hydroxyl groups.

The loss of hydroxyl group produces initial carbocation. The initial carbocation results in the most stable carbocation.

In the next step, the water molecule departs, and an alkyl group from the adjacent carbon atom migrates to its position.

A new carbocation is created, where the hydroxyl group is attached to the carbon bearing the positive charge.

The unshared electrons pair on this hydroxyl group stabilizes the carbocation.

The final step is the formation of a carbonyl group and abstraction of a proton from the oxygen atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

3) Determine if the pairs are constitutional isomers, enantiomers, diastereomers, or mesocompounds. (4 points)

In the decomposition reaction in solution B → C, only species C absorbs UV radiation, but neither B nor the solvent absorbs. If we call At the absorbance measured at any time, A0 the absorbance at the beginning of the reaction, and A∞ the absorbance at the end of the reaction, which of the expressions is valid? We assume that Beer's law is fulfilled.

> You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: 1. ☑ CI 2. H3O+ O Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. Explanation Check ? DO 18 Ar B © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 16, Problem 46DSP

Interpretation Introduction

Interpretation:

The structure of a ketone formed in 73% yield in the pinacol re-arrangement which proceeds by the way of more stable of the two carbocations formed of the given vicinal diol is to be chosen.

Concept Introduction:

During pinacol re-arrangement, a diol is converted to a ketone.

The reaction begins by protonation of one of the hydroxyl groups.

The loss of hydroxyl group produces initial carbocation. The initial carbocation results in the most stable carbocation.

In the next step, the water molecule departs, and an alkyl group from the adjacent carbon atom migrates to its position.

A new carbocation is created, where the hydroxyl group is attached to the carbon bearing the positive charge.

The unshared electrons pair on this hydroxyl group stabilizes the carbocation.

The final step is the formation of a carbonyl group and abstraction of a proton from the oxygen atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 16, Problem 46DSP

Interpretation Introduction

Interpretation:

The structure of a ketone formed in 73% yield in the pinacol re-arrangement which proceeds by the way of more stable of the two carbocations formed of the given vicinal diol is to be chosen.

Concept Introduction:

During pinacol re-arrangement, a diol is converted to a ketone.

The reaction begins by protonation of one of the hydroxyl groups.

The loss of hydroxyl group produces initial carbocation. The initial carbocation results in the most stable carbocation.

In the next step, the water molecule departs, and an alkyl group from the adjacent carbon atom migrates to its position.

A new carbocation is created, where the hydroxyl group is attached to the carbon bearing the positive charge.

The unshared electrons pair on this hydroxyl group stabilizes the carbocation.

The final step is the formation of a carbonyl group and abstraction of a proton from the oxygen atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 16, Problem 46DSP

Interpretation Introduction