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

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 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

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 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