Given that to be aromatic , a molecule must have (4n+2) Ï€ electrons and must have a planar monocyclic system of conjugation. Cyclodecapentaene fulfills one of these criteria but not the other and has resisted all attempts at synthesis. This observation is to be explained. Concept introduction: According to Huckel’s rule, a molecule orb an ion or bradical will be stable and aromatic if it is planar, cyclic and conjugated (4n+2) electrons. For a cyclic system to be aromatic both conditions are to be satisfied. If only one of the conditions is satisfied the specie will not be aromatic, becomes less stable and cannot be synthesized. To explain: The observation that cyclodecapentaene fulfills one of the criteria for aromaticity but not the other and has resisted all attempts at synthesis.

Question

Compound A whose molecular formula is C9H11ClO, is found to be aromatic, and on vigorous oxidation with hot, concentrated, basic potassium permanganate followed by acidification, a new aromatic, compound B with the molecular formula of C7H5ClO2 is formed. On treatment with bromine and a ferric bromide catalyst, compound B produces ONLY 2 monobrominated derivatives, compounds C and D, each having the molecular formula C7H4BrClO2. On treatment with sodium metal, compound A produces bubbles of hydrogen gas. Controlled oxidation of compound A with PCC first gives compound E, with formula C9H9ClO. Compound E produces a silver mirror with Tollen’s reagent. Mild oxidation of compound E by chromic acid produces compound F, with the molecular formula C9H9ClO2 which turns blue litmus red. When compound A is heated with concentrated sulfuric acid, a single compound G, whose molecular formula is C9H9Cl, is produced. On ozonolysis followed by reaction with dimethyl sulfide, compound G gives…

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 15.3, Problem 5P

Interpretation Introduction

Interpretation:

Given that to be aromatic, a molecule must have (4n+2) Ï€ electrons and must have a planar monocyclic system of conjugation. Cyclodecapentaene fulfills one of these criteria but not the other and has resisted all attempts at synthesis. This observation is to be explained.

Concept introduction:

According to Huckel’s rule, a molecule orb an ion or bradical will be stable and aromatic if it is planar, cyclic and conjugated (4n+2) electrons. For a cyclic system to be aromatic both conditions are to be satisfied. If only one of the conditions is satisfied the specie will not be aromatic, becomes less stable and cannot be synthesized.

To explain:

The observation that cyclodecapentaene fulfills one of the criteria for aromaticity but not the other and has resisted all attempts at synthesis.

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Compound A whose molecular formula is C9H11ClO, is found to be aromatic, and on vigorous oxidation with hot, concentrated, basic potassium permanganate followed by acidification, a new aromatic, compound B with the molecular formula of C7H5ClO2 is formed. On treatment with bromine and a ferric bromide catalyst, compound B produces ONLY 2 monobrominated derivatives, compounds C and D, each having the molecular formula C7H4BrClO2. On treatment with sodium metal, compound A produces bubbles of hydrogen gas. Controlled oxidation of compound A with PCC first gives compound E, with formula C9H9ClO. Compound E produces a silver mirror with Tollen’s reagent. Mild oxidation of compound E by chromic acid produces compound F, with the molecular formula C9H9ClO2 which turns blue litmus red. When compound A is heated with concentrated sulfuric acid, a single compound G, whose molecular formula is C9H9Cl, is produced. On ozonolysis followed by reaction with dimethyl sulfide, compound G gives…

Which of the following are consistent with the requirements for aromaticity?I. A system with delocalized p electrons in a ring.II. 4n p electrons in the ring.III. All the ring atoms must be carbons.IV. (4n + 2) p electrons in the ring. Give the answer why.

Starting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.)2,4,6-Trinitrotoluene (TNT)

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 15.3, Problem 5P

Interpretation Introduction

Interpretation:

Given that to be aromatic, a molecule must have (4n+2) Ï€ electrons and must have a planar monocyclic system of conjugation. Cyclodecapentaene fulfills one of these criteria but not the other and has resisted all attempts at synthesis. This observation is to be explained.

Concept introduction:

According to Huckel’s rule, a molecule orb an ion or bradical will be stable and aromatic if it is planar, cyclic and conjugated (4n+2) electrons. For a cyclic system to be aromatic both conditions are to be satisfied. If only one of the conditions is satisfied the specie will not be aromatic, becomes less stable and cannot be synthesized.

To explain:

The observation that cyclodecapentaene fulfills one of the criteria for aromaticity but not the other and has resisted all attempts at synthesis.

Expert Solution & Answer

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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 15.3, Problem 5P

Interpretation Introduction

Interpretation:

Given that to be aromatic, a molecule must have (4n+2) Ï€ electrons and must have a planar monocyclic system of conjugation. Cyclodecapentaene fulfills one of these criteria but not the other and has resisted all attempts at synthesis. This observation is to be explained.

Concept introduction:

According to Huckel’s rule, a molecule orb an ion or bradical will be stable and aromatic if it is planar, cyclic and conjugated (4n+2) electrons. For a cyclic system to be aromatic both conditions are to be satisfied. If only one of the conditions is satisfied the specie will not be aromatic, becomes less stable and cannot be synthesized.

To explain:

The observation that cyclodecapentaene fulfills one of the criteria for aromaticity but not the other and has resisted all attempts at synthesis.

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 15.3, Problem 5P

Interpretation Introduction