Given an optically active alcohol, A has the molecular formula C 11 H 16 O. It does not adsorb any hydrogen during catalytic reduction in the presence of Pd. It gets dehydrated when treated with dilute sulphuric acid to yield an optically inactive alkene , B (C 11 H 14 ). The alkene B yields propanol, CH 3 CH 2 CHO and a ketone, C (C 8 H 8 O). The number of degrees of unsaturation in A is to be calculated. A, B and C are to be identified and the reactions are to be written. Concept introduction: The degree of unsaturation in a compound can be calculated by considering the molecular formula of the compound and its parent hydrocarbon. Any compound with a chiral centre will be optically active. Alcohols undergo dehydration when warmed with dilute sulphuric acid. During ozonolysis the double bond is cleaved to yield carbonyl compounds. If the doubly bonded carbon is disubstituted then ketones are produced and if the doubly bonded carbon is monoisubstituted then aldehydes are produced. To calculate: The number of degrees of unsaturation in compound A. To identify: The structures of compounds A, B and C. To write: The reactions given.

Question

Compound A, C11H16O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H2SO4, dehydration occurred and an optically inactive alkene B, C11H14 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C8H8O, was shown to be a methyl ketone while product D, C3H6O, was shown to be an aldehyde.

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 8.SE, Problem 72AP

Interpretation Introduction

Interpretation:

Given an optically active alcohol, A has the molecular formula C₁₁H₁₆O. It does not adsorb any hydrogen during catalytic reduction in the presence of Pd. It gets dehydrated when treated with dilute sulphuric acid to yield an optically inactive alkene, B (C₁₁H₁₄). The alkene B yields propanol, CH₃CH₂CHO and a ketone, C (C₈H₈O). The number of degrees of unsaturation in A is to be calculated. A, B and C are to be identified and the reactions are to be written.

Concept introduction:

The degree of unsaturation in a compound can be calculated by considering the molecular formula of the compound and its parent hydrocarbon. Any compound with a chiral centre will be optically active. Alcohols undergo dehydration when warmed with dilute sulphuric acid. During ozonolysis the double bond is cleaved to yield carbonyl compounds. If the doubly bonded carbon is disubstituted then ketones are produced and if the doubly bonded carbon is monoisubstituted then aldehydes are produced.

To calculate:

The number of degrees of unsaturation in compound A.

To identify:

The structures of compounds A, B and C.

To write:

The reactions given.

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Compound A, C11H16O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H2SO4, dehydration occurred and an optically inactive alkene B, C11H14 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C8H8O, was shown to be a methyl ketone while product D, C3H6O, was shown to be an aldehyde.

Compound A, C11H16O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H2SO4, dehydration occurred and an optically inactive alkene B, C11H14 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C7H6O, was shown to be an aldehyde while product D, C4H8O, was shown to be a ketone. Draw the structure of compound C. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. HELP PLEASE I DONT UNDERSTAND THE PROCESS

An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.

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 8.SE, Problem 72AP

Interpretation Introduction

Interpretation:

Given an optically active alcohol, A has the molecular formula C₁₁H₁₆O. It does not adsorb any hydrogen during catalytic reduction in the presence of Pd. It gets dehydrated when treated with dilute sulphuric acid to yield an optically inactive alkene, B (C₁₁H₁₄). The alkene B yields propanol, CH₃CH₂CHO and a ketone, C (C₈H₈O). The number of degrees of unsaturation in A is to be calculated. A, B and C are to be identified and the reactions are to be written.

Concept introduction:

The degree of unsaturation in a compound can be calculated by considering the molecular formula of the compound and its parent hydrocarbon. Any compound with a chiral centre will be optically active. Alcohols undergo dehydration when warmed with dilute sulphuric acid. During ozonolysis the double bond is cleaved to yield carbonyl compounds. If the doubly bonded carbon is disubstituted then ketones are produced and if the doubly bonded carbon is monoisubstituted then aldehydes are produced.

To calculate:

The number of degrees of unsaturation in compound A.

To identify:

The structures of compounds A, B and C.

To write:

The reactions given.

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 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 8.SE, Problem 72AP

Interpretation Introduction

Interpretation:

Given an optically active alcohol, A has the molecular formula C₁₁H₁₆O. It does not adsorb any hydrogen during catalytic reduction in the presence of Pd. It gets dehydrated when treated with dilute sulphuric acid to yield an optically inactive alkene, B (C₁₁H₁₄). The alkene B yields propanol, CH₃CH₂CHO and a ketone, C (C₈H₈O). The number of degrees of unsaturation in A is to be calculated. A, B and C are to be identified and the reactions are to be written.

Concept introduction:

The degree of unsaturation in a compound can be calculated by considering the molecular formula of the compound and its parent hydrocarbon. Any compound with a chiral centre will be optically active. Alcohols undergo dehydration when warmed with dilute sulphuric acid. During ozonolysis the double bond is cleaved to yield carbonyl compounds. If the doubly bonded carbon is disubstituted then ketones are produced and if the doubly bonded carbon is monoisubstituted then aldehydes are produced.

To calculate:

The number of degrees of unsaturation in compound A.

To identify:

The structures of compounds A, B and C.

To write:

The reactions given.

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 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 8.SE, Problem 72AP

Interpretation Introduction