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

Predict the major organic product(s) of the following reactions. Indicate which of the following mechanisms is in operation: SN1, SN2, E1, or E2.

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Predict the major organic product(s) of the following reactions. Indicate which of the following mechanisms is in operation: SN1, SN2, E1, or E2.

(c) (4pts) Mechanism: heat (E1) CH3OH + 1.5pts each _E1 _ (1pt) Br CH3OH (d) (4pts) Mechanism: SN1 (1pt) (e) (3pts) 1111 I H 10 Ill!! H LDA THF (solvent) Mechanism: E2 (1pt) NC (f) Bri!!!!! CH3 NaCN (3pts) acetone Mechanism: SN2 (1pt) (SN1) -OCH3 OCH3 1.5pts each 2pts for either product 1pt if incorrect stereochemistry H Br (g) “,、 (3pts) H CH3OH +21 Mechanism: SN2 (1pt) H CH3 2pts 1pt if incorrect stereochemistry H 2pts 1pt if incorrect stereochemistry

A mixture of butyl acrylate and 4'-chloropropiophenone has been taken for proton NMR analysis. Based on this proton NMR, determine the relative percentage of each compound in the mixture

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