It is to be determined which of the two given molecules D and E would be expected to undergo hydration to a greater extent. Concept introduction: The carbon atom in the carbonyl group is relatively electron-poor, and a nucleophile such as water can attack this carbon. This bond formation and subsequent solvent-mediated proton transfer result in the formation of a geminal diol . The overall reaction is equivalent to the hydration of the carbonyl group. In ketones , there are two alkyl groups attached to the carbonyl carbon, so the inductive effect does not differ much from molecule to molecule. The extent of hydration then depends primarily on the steric effect associated with the alkyl groups. The presence of bulky groups on the carbonyl carbon makes it more difficult for the nucleophile to attack, reducing the extent of hydration. The steric crowding in the hydrate with two bulky alkyl groups also makes it less stable.

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 17, Problem 17.4P

Interpretation Introduction

Interpretation:

It is to be determined which of the two given molecules D and E would be expected to undergo hydration to a greater extent.

Concept introduction:

The carbon atom in the carbonyl group is relatively electron-poor, and a nucleophile such as water can attack this carbon. This bond formation and subsequent solvent-mediated proton transfer result in the formation of a geminal diol. The overall reaction is equivalent to the hydration of the carbonyl group.

In ketones, there are two alkyl groups attached to the carbonyl carbon, so the inductive effect does not differ much from molecule to molecule. The extent of hydration then depends primarily on the steric effect associated with the alkyl groups.

The presence of bulky groups on the carbonyl carbon makes it more difficult for the nucleophile to attack, reducing the extent of hydration. The steric crowding in the hydrate with two bulky alkyl groups also makes it less stable.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

PROPOSE REACTION MECHANISM FOR ACID-CATALYZED REACTION OF 3-PENTANONE WITH DIMETHYLAMINE

Assign all the protons

Assign all the carbons

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 17, Problem 17.4P

Interpretation Introduction

Interpretation:

It is to be determined which of the two given molecules D and E would be expected to undergo hydration to a greater extent.

Concept introduction:

The carbon atom in the carbonyl group is relatively electron-poor, and a nucleophile such as water can attack this carbon. This bond formation and subsequent solvent-mediated proton transfer result in the formation of a geminal diol. The overall reaction is equivalent to the hydration of the carbonyl group.

In ketones, there are two alkyl groups attached to the carbonyl carbon, so the inductive effect does not differ much from molecule to molecule. The extent of hydration then depends primarily on the steric effect associated with the alkyl groups.

The presence of bulky groups on the carbonyl carbon makes it more difficult for the nucleophile to attack, reducing the extent of hydration. The steric crowding in the hydrate with two bulky alkyl groups also makes it less stable.

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 17, Problem 17.4P

Interpretation Introduction

Interpretation:

It is to be determined which of the two given molecules D and E would be expected to undergo hydration to a greater extent.

Concept introduction:

The carbon atom in the carbonyl group is relatively electron-poor, and a nucleophile such as water can attack this carbon. This bond formation and subsequent solvent-mediated proton transfer result in the formation of a geminal diol. The overall reaction is equivalent to the hydration of the carbonyl group.

In ketones, there are two alkyl groups attached to the carbonyl carbon, so the inductive effect does not differ much from molecule to molecule. The extent of hydration then depends primarily on the steric effect associated with the alkyl groups.

The presence of bulky groups on the carbonyl carbon makes it more difficult for the nucleophile to attack, reducing the extent of hydration. The steric crowding in the hydrate with two bulky alkyl groups also makes it less stable.

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 17, Problem 17.4P

Interpretation Introduction