The observation that cycloheptatrienone is stable but cyclopentadienone is so reactive and cannot be isolated is to be explained taking into account the polarity of the carbonyl group. Concept introduction: Carbonyl group is polar as oxygen is more electronegative than carbon. According to Huckel’s rule, any specie that is cyclic, planar and has (4n+2) delocalized Ï€ electrons will be aromatic and stable. Thus species with 2, 6, 10, 14 etc. Ï€ electrons will be aromatic and stable. To explain: The observation that cycloheptatrienone is stable but cyclopentadienone is so reactive and cannot be isolated is taking into account the polarity of the carbonyl group.

Question

Explain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.

Answer 1

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 32AP

Interpretation Introduction

Interpretation:

The observation that cycloheptatrienone is stable but cyclopentadienone is so reactive and cannot be isolated is to be explained taking into account the polarity of the carbonyl group.

Concept introduction:

Carbonyl group is polar as oxygen is more electronegative than carbon. According to Huckel’s rule, any specie that is cyclic, planar and has (4n+2) delocalized Ï€ electrons will be aromatic and stable. Thus species with 2, 6, 10, 14 etc. Ï€ electrons will be aromatic and stable.

To explain:

The observation that cycloheptatrienone is stable but cyclopentadienone is so reactive and cannot be isolated is taking into account the polarity of the carbonyl group.

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Answer 2

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 32AP

Interpretation Introduction

Interpretation:

The observation that cycloheptatrienone is stable but cyclopentadienone is so reactive and cannot be isolated is to be explained taking into account the polarity of the carbonyl group.

Concept introduction:

Carbonyl group is polar as oxygen is more electronegative than carbon. According to Huckel’s rule, any specie that is cyclic, planar and has (4n+2) delocalized Ï€ electrons will be aromatic and stable. Thus species with 2, 6, 10, 14 etc. Ï€ electrons will be aromatic and stable.

To explain:

The observation that cycloheptatrienone is stable but cyclopentadienone is so reactive and cannot be isolated is taking into account the polarity of the carbonyl group.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 3

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 32AP

Interpretation Introduction

Interpretation:

The observation that cycloheptatrienone is stable but cyclopentadienone is so reactive and cannot be isolated is to be explained taking into account the polarity of the carbonyl group.

Concept introduction:

Carbonyl group is polar as oxygen is more electronegative than carbon. According to Huckel’s rule, any specie that is cyclic, planar and has (4n+2) delocalized Ï€ electrons will be aromatic and stable. Thus species with 2, 6, 10, 14 etc. Ï€ electrons will be aromatic and stable.

To explain:

The observation that cycloheptatrienone is stable but cyclopentadienone is so reactive and cannot be isolated is taking into account the polarity of the carbonyl group.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 32AP

Interpretation Introduction