A structure for the compound B (an isomer of A in the problem 19-81) with the following descriptions is to be proposed. IR: 1730 cm -1 ; 1 HNMR: 2.75 δ (Rel.area=2.00), 2.95 δ (Rel.area=2.00), 7.23 δ (Rel.area=3.00), 7.31 δ (Rel.area=2.00), 9.82 δ (Rel.area=1.00). Concept introduction: Aldehydes and ketones show a strong absorption band in IR from 1660-1770 cm -1 . Aldehydes show two characteristic C-H absorptions between 2700-2760 cm -1 and 2800-2860 cm -1 . Saturated aldehydes absorb near 1730 cm -1 while aromatic aldehydes and α, β-unsaturated aldehydes absorb near 1705 cm -1 . Saturated ketones and cyclohexanones absorb near 1715 cm -1 while aromatic ketones and α, β-unsaturated ketones absorb near 1685-1690 cm -1 . Cyclopentanones absorb around 1750 cm -1 . In 1 HNMR the aldehyde protons absorb near 10 δ with a coupling constant, J=3Hz. Hydrogens on the carbon next to aldehyde group absorb near 2.0-2.3 δ. Methyl ketones show a sharp three proton singlet near 2.1 δ. To propose: A structure for the compound B (an isomer of A in the problem 19-81) with the following descriptions is to be proposed. IR: 1730 cm -1 ; 1 HNMR: 2.75 δ (Rel.area=2.00), 2.95 δ (Rel.area=2.00), 7.23 δ (Rel.area=3.00), 7.31 δ (Rel.area=2.00), 9.82 δ (Rel.area=1.00).

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Answer 1

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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 19.SE, Problem 82AP

Interpretation Introduction

Interpretation:

A structure for the compound B (an isomer of A in the problem 19-81) with the following descriptions is to be proposed.

IR: 1730 cm^-1; ¹HNMR: 2.75 δ (Rel.area=2.00), 2.95 δ (Rel.area=2.00), 7.23 δ (Rel.area=3.00), 7.31 δ (Rel.area=2.00), 9.82 δ (Rel.area=1.00).

Concept introduction:

Aldehydes and ketones show a strong absorption band in IR from 1660-1770 cm^-1. Aldehydes show two characteristic C-H absorptions between 2700-2760 cm^-1 and 2800-2860 cm^-1. Saturated aldehydes absorb near 1730 cm^-1 while aromatic aldehydes and α, β-unsaturated aldehydes absorb near 1705 cm^-1. Saturated ketones and cyclohexanones absorb near 1715 cm^-1 while aromatic ketones and α, β-unsaturated ketones absorb near 1685-1690 cm^-1. Cyclopentanones absorb around 1750 cm^-1.

In ¹HNMR the aldehyde protons absorb near 10 δ with a coupling constant, J=3Hz. Hydrogens on the carbon next to aldehyde group absorb near 2.0-2.3 δ. Methyl ketones show a sharp three proton singlet near 2.1 δ.

To propose:

A structure for the compound B (an isomer of A in the problem 19-81) with the following descriptions is to be proposed.

IR: 1730 cm^-1; ¹HNMR: 2.75 δ (Rel.area=2.00), 2.95 δ (Rel.area=2.00), 7.23 δ (Rel.area=3.00), 7.31 δ (Rel.area=2.00), 9.82 δ (Rel.area=1.00).

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Compounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.

As we will learn in Chapter 17, reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600−3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?

As we will learn in Chapter 20, reaction of (CH3)2CO with LiC ≡ CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600–3200, 3303, 2938, and 2120 cm. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?

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 19.SE, Problem 82AP

Interpretation Introduction

Interpretation:

A structure for the compound B (an isomer of A in the problem 19-81) with the following descriptions is to be proposed.

IR: 1730 cm^-1; ¹HNMR: 2.75 δ (Rel.area=2.00), 2.95 δ (Rel.area=2.00), 7.23 δ (Rel.area=3.00), 7.31 δ (Rel.area=2.00), 9.82 δ (Rel.area=1.00).

Concept introduction:

Aldehydes and ketones show a strong absorption band in IR from 1660-1770 cm^-1. Aldehydes show two characteristic C-H absorptions between 2700-2760 cm^-1 and 2800-2860 cm^-1. Saturated aldehydes absorb near 1730 cm^-1 while aromatic aldehydes and α, β-unsaturated aldehydes absorb near 1705 cm^-1. Saturated ketones and cyclohexanones absorb near 1715 cm^-1 while aromatic ketones and α, β-unsaturated ketones absorb near 1685-1690 cm^-1. Cyclopentanones absorb around 1750 cm^-1.

In ¹HNMR the aldehyde protons absorb near 10 δ with a coupling constant, J=3Hz. Hydrogens on the carbon next to aldehyde group absorb near 2.0-2.3 δ. Methyl ketones show a sharp three proton singlet near 2.1 δ.

To propose:

A structure for the compound B (an isomer of A in the problem 19-81) with the following descriptions is to be proposed.

IR: 1730 cm^-1; ¹HNMR: 2.75 δ (Rel.area=2.00), 2.95 δ (Rel.area=2.00), 7.23 δ (Rel.area=3.00), 7.31 δ (Rel.area=2.00), 9.82 δ (Rel.area=1.00).

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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 19.SE, Problem 82AP

Interpretation Introduction

Interpretation:

A structure for the compound B (an isomer of A in the problem 19-81) with the following descriptions is to be proposed.

IR: 1730 cm^-1; ¹HNMR: 2.75 δ (Rel.area=2.00), 2.95 δ (Rel.area=2.00), 7.23 δ (Rel.area=3.00), 7.31 δ (Rel.area=2.00), 9.82 δ (Rel.area=1.00).

Concept introduction:

Aldehydes and ketones show a strong absorption band in IR from 1660-1770 cm^-1. Aldehydes show two characteristic C-H absorptions between 2700-2760 cm^-1 and 2800-2860 cm^-1. Saturated aldehydes absorb near 1730 cm^-1 while aromatic aldehydes and α, β-unsaturated aldehydes absorb near 1705 cm^-1. Saturated ketones and cyclohexanones absorb near 1715 cm^-1 while aromatic ketones and α, β-unsaturated ketones absorb near 1685-1690 cm^-1. Cyclopentanones absorb around 1750 cm^-1.

In ¹HNMR the aldehyde protons absorb near 10 δ with a coupling constant, J=3Hz. Hydrogens on the carbon next to aldehyde group absorb near 2.0-2.3 δ. Methyl ketones show a sharp three proton singlet near 2.1 δ.

To propose:

A structure for the compound B (an isomer of A in the problem 19-81) with the following descriptions is to be proposed.

IR: 1730 cm^-1; ¹HNMR: 2.75 δ (Rel.area=2.00), 2.95 δ (Rel.area=2.00), 7.23 δ (Rel.area=3.00), 7.31 δ (Rel.area=2.00), 9.82 δ (Rel.area=1.00).

Expert Solution & Answer

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Check out a sample textbook solution

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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 19.SE, Problem 82AP

Interpretation Introduction