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

Q4: Rank the relative nucleophilicity of halide ions in water solution and DMF solution, respectively. F CI Br | Q5: Determine which of the substrates will and will not react with NaSCH3 in an SN2 reaction to have a reasonable yield of product. NH2 Br Br Br OH Br

Q7: Rank the following groups in order of basicity, nucleophilicity, and leaving group ability. a) H₂O, OH, CH3COOT b) NH3, H₂O, H₂S

Q8: Rank the following compounds in order of increasing reactivity in a nucleophilic substitution reaction with CN as the nucleophile. Br A B NH2 LL F C D OH CI LLI E Q9: Complete the missing entities for following reactions (e.g., major product(s), reactants, and/or solvents) for the SN2 reactions to occur efficiently. Include curved-arrow mechanism for reactions a) to d). a) H "Cl D + -OCH 3 Page 3 of 5

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