Compound A, C 10 H 18 O, when warmed with dilute H 2 SO 4 at 50 o C yields a mixture of two alkenes , C 10 H 16 . The major alkene product, B, gives only cyclopentanone upon ozonolysis followed by reduction with zinc in acetic acid. Compounds A and B are to be identified and the reactions are to be written. Concept introduction: Alcohols gets dehydrated to yield alkenes when warmed with dilute H 2 SO 4 at 50 o C. Symmetrical alkenes upon ozonolysis followed by reduction with zinc in acetic acid will yield only a single product. If the doubly bonded carbons are attached to two substituents then upon ozonolysis a ketone is produced. To identify: The compounds A and B based on the reactions given and to explain the reactions.

Question

Compound A (C11H23Br) is a secondary alkyl halide. On being heated with a solution of sodium ethoxide in ethanol, compound A yielded a mixture of two alkenes B and C, each having molecular formula C11H22. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3,5-diethylheptane. Draw structures for compounds A, B, and C consistent with these observations.

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 8.SE, Problem 61AP

Interpretation Introduction

Interpretation:

Compound A, C₁₀H₁₈O, when warmed with dilute H₂SO₄ at 50^oC yields a mixture of two alkenes, C₁₀H₁₆. The major alkene product, B, gives only cyclopentanone upon ozonolysis followed by reduction with zinc in acetic acid. Compounds A and B are to be identified and the reactions are to be written.

Concept introduction:

Alcohols gets dehydrated to yield alkenes when warmed with dilute H₂SO₄ at 50^oC. Symmetrical alkenes upon ozonolysis followed by reduction with zinc in acetic acid will yield only a single product. If the doubly bonded carbons are attached to two substituents then upon ozonolysis a ketone is produced.

To identify:

The compounds A and B based on the reactions given and to explain the reactions.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Compound A (C11H23Br) is a secondary alkyl halide. On being heated with a solution of sodium ethoxide in ethanol, compound A yielded a mixture of two alkenes B and C, each having molecular formula C11H22. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3,5-diethylheptane. Draw structures for compounds A, B, and C consistent with these observations.

5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.

Compound A (C6H12O2) reacts with water, acid, and heatto yield compound B (C5H10O2) and compound C (CH4O).Compound B is acidic. Deduce possible structures of compounds A, B, and C

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 8.SE, Problem 61AP

Interpretation Introduction

Interpretation:

Compound A, C₁₀H₁₈O, when warmed with dilute H₂SO₄ at 50^oC yields a mixture of two alkenes, C₁₀H₁₆. The major alkene product, B, gives only cyclopentanone upon ozonolysis followed by reduction with zinc in acetic acid. Compounds A and B are to be identified and the reactions are to be written.

Concept introduction:

Alcohols gets dehydrated to yield alkenes when warmed with dilute H₂SO₄ at 50^oC. Symmetrical alkenes upon ozonolysis followed by reduction with zinc in acetic acid will yield only a single product. If the doubly bonded carbons are attached to two substituents then upon ozonolysis a ketone is produced.

To identify:

The compounds A and B based on the reactions given and to explain the reactions.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 8.SE, Problem 61AP

Interpretation Introduction

Interpretation:

Compound A, C₁₀H₁₈O, when warmed with dilute H₂SO₄ at 50^oC yields a mixture of two alkenes, C₁₀H₁₆. The major alkene product, B, gives only cyclopentanone upon ozonolysis followed by reduction with zinc in acetic acid. Compounds A and B are to be identified and the reactions are to be written.

Concept introduction:

Alcohols gets dehydrated to yield alkenes when warmed with dilute H₂SO₄ at 50^oC. Symmetrical alkenes upon ozonolysis followed by reduction with zinc in acetic acid will yield only a single product. If the doubly bonded carbons are attached to two substituents then upon ozonolysis a ketone is produced.

To identify:

The compounds A and B based on the reactions given and to explain the reactions.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 8.SE, Problem 61AP

Interpretation Introduction