Compound A, C 10 H 18 O undergoes reaction with dil.H 2 SO 4 at 25 o C to yield a mixture of two alkenes C 10 H 16 . The major alkene product, B, gives only cyclopentanone after ozone treatment followed by reduction with Zn in acetic acid. The reactions involved are to be written and the compounds A and B are to be identified. Concept introduction: Alcohols undergo dehydration on treatment with dil.H 2 SO 4 . The hydrogen required for removing water comes from an adjacent carbon. If two alternate possibilities exist both can be eliminated leading to a mixture of alkenes. During ozonolysis followed by reduction, the double bond in an alkene is cleaved and the two carbons in double bond each get attached to an oxygen atom resulting in the formation of aldehydes or ketones. To give: The structure of compound A, C 10 H 18 O, which gives a mixture of two alkenes, C 10 H 16 , when treated with dil.H 2 SO 4 at 25 o C and that of B which gives only cyclopentanone after ozone treatment followed by reduction with Zn in acetic acid and to write the reactions involved.

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 aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.SE, Problem 65AP

Interpretation Introduction

Interpretation:

Compound A, C₁₀H₁₈O undergoes reaction with dil.H₂SO₄ at 25^oC to yield a mixture of two alkenes C₁₀H₁₆. The major alkene product, B, gives only cyclopentanone after ozone treatment followed by reduction with Zn in acetic acid. The reactions involved are to be written and the compounds A and B are to be identified.

Concept introduction:

Alcohols undergo dehydration on treatment with dil.H₂SO₄. The hydrogen required for removing water comes from an adjacent carbon. If two alternate possibilities exist both can be eliminated leading to a mixture of alkenes.

During ozonolysis followed by reduction, the double bond in an alkene is cleaved and the two carbons in double bond each get attached to an oxygen atom resulting in the formation of aldehydes or ketones.

To give:

The structure of compound A, C₁₀H₁₈O, which gives a mixture of two alkenes, C₁₀H₁₆, when treated with dil.H₂SO₄ at 25^oC and that of B which gives only cyclopentanone after ozone treatment followed by reduction with Zn in acetic acid and to write the reactions involved.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

2. Name the following hydrocarbons. (9 marks) a) HHHHHHHH H-C-C- H-O-S b) HCEC-CH3 H H H H H d) c) H C=C- H H H e) CH3 CH3 CH2CH=CH-CH=CHCH3 HHHH H-C-C-C-C-H H HH H f) large CH2CH3 pola H3C section lovels tower, able ocart firs g) Tower H3C-CH2 then in H3C-CH-CH-CH3 enblbano bne noitsidab Copyright © 2008. Durham Continuing Education CH3

Name the molecules & Identify any chiral center CH3CH2CH2CHCH₂CH₂CH₂CH₂ OH CH₂CHCH2CH3 Br CH3 CH3CHCH2CHCH2CH3 CH3

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electrons-pushing arrows for the following reaction or mechanistic step(s).

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.SE, Problem 65AP

Interpretation Introduction

Interpretation:

Compound A, C₁₀H₁₈O undergoes reaction with dil.H₂SO₄ at 25^oC to yield a mixture of two alkenes C₁₀H₁₆. The major alkene product, B, gives only cyclopentanone after ozone treatment followed by reduction with Zn in acetic acid. The reactions involved are to be written and the compounds A and B are to be identified.

Concept introduction:

Alcohols undergo dehydration on treatment with dil.H₂SO₄. The hydrogen required for removing water comes from an adjacent carbon. If two alternate possibilities exist both can be eliminated leading to a mixture of alkenes.

During ozonolysis followed by reduction, the double bond in an alkene is cleaved and the two carbons in double bond each get attached to an oxygen atom resulting in the formation of aldehydes or ketones.

To give:

The structure of compound A, C₁₀H₁₈O, which gives a mixture of two alkenes, C₁₀H₁₆, when treated with dil.H₂SO₄ at 25^oC and that of B which gives only cyclopentanone after ozone treatment followed by reduction with Zn in acetic acid and to write the reactions involved.

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 aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.SE, Problem 65AP

Interpretation Introduction

Interpretation:

Compound A, C₁₀H₁₈O undergoes reaction with dil.H₂SO₄ at 25^oC to yield a mixture of two alkenes C₁₀H₁₆. The major alkene product, B, gives only cyclopentanone after ozone treatment followed by reduction with Zn in acetic acid. The reactions involved are to be written and the compounds A and B are to be identified.

Concept introduction:

Alcohols undergo dehydration on treatment with dil.H₂SO₄. The hydrogen required for removing water comes from an adjacent carbon. If two alternate possibilities exist both can be eliminated leading to a mixture of alkenes.

During ozonolysis followed by reduction, the double bond in an alkene is cleaved and the two carbons in double bond each get attached to an oxygen atom resulting in the formation of aldehydes or ketones.

To give:

The structure of compound A, C₁₀H₁₈O, which gives a mixture of two alkenes, C₁₀H₁₆, when treated with dil.H₂SO₄ at 25^oC and that of B which gives only cyclopentanone after ozone treatment followed by reduction with Zn in acetic acid and to write the reactions involved.

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 aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.SE, Problem 65AP

Interpretation Introduction