A structure for the compound A, C 8 H 10 O 2 , with the following spectral data is to be proposed. IR: 1750 cm -1 ; 13 CNMR: 219 δ (20), two signals between 35 δ to 45 δ. 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 2700-2760cm -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 13 CNMR, carbons in double bond which are sp2 hybridized absorb from 110 to 220 δ. Saturated aldehydes and ketones usually absorb in the region from 200 to 215 δ While aromatic and unsaturated carbonyl compounds absorb in the 190 to 200 δ region. The primary alkyl carbon absorbs in the range 10-15δ, a secondary alkyl radical in the range 16-25δ while a tertiary alkyl in the range 25-35 δ. To propose: A structure for the compound A, C 8 H 10 O 2 , with the following spectral data. IR: 1750 cm -1 ; 13 CNMR: 219 δ (20), two signals between 35 δ to 45 δ.

Question

Treatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.

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 19.SE, Problem 70AP

Interpretation Introduction

Interpretation:

A structure for the compound A, C₈H₁₀O₂, with the following spectral data is to be proposed.

IR: 1750 cm^-1; ¹³CNMR: 219 δ (20), two signals between 35 δ to 45 δ.

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 2700-2760cm^-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 ¹³CNMR, carbons in double bond which are sp2 hybridized absorb from 110 to 220 δ. Saturated aldehydes and ketones usually absorb in the region from 200 to 215 δ While aromatic and unsaturated carbonyl compounds absorb in the 190 to 200 δ region. The primary alkyl carbon absorbs in the range 10-15δ, a secondary alkyl radical in the range 16-25δ while a tertiary alkyl in the range 25-35 δ.

To propose:

A structure for the compound A, C₈H₁₀O₂, with the following spectral data.

IR: 1750 cm^-1; ¹³CNMR: 219 δ (20), two signals between 35 δ to 45 δ.

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Treatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.

Propose a structure for D (molecular formula C9H9ClO2) consistent with the given spectroscopic data. 13C NMR signals at 30, 36, 128, 130, 133, 139, and 179 ppm

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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 70AP

Interpretation Introduction

Interpretation:

A structure for the compound A, C₈H₁₀O₂, with the following spectral data is to be proposed.

IR: 1750 cm^-1; ¹³CNMR: 219 δ (20), two signals between 35 δ to 45 δ.

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 2700-2760cm^-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 ¹³CNMR, carbons in double bond which are sp2 hybridized absorb from 110 to 220 δ. Saturated aldehydes and ketones usually absorb in the region from 200 to 215 δ While aromatic and unsaturated carbonyl compounds absorb in the 190 to 200 δ region. The primary alkyl carbon absorbs in the range 10-15δ, a secondary alkyl radical in the range 16-25δ while a tertiary alkyl in the range 25-35 δ.

To propose:

A structure for the compound A, C₈H₁₀O₂, with the following spectral data.

IR: 1750 cm^-1; ¹³CNMR: 219 δ (20), two signals between 35 δ to 45 δ.

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 19.SE, Problem 70AP

Interpretation Introduction

Interpretation:

A structure for the compound A, C₈H₁₀O₂, with the following spectral data is to be proposed.

IR: 1750 cm^-1; ¹³CNMR: 219 δ (20), two signals between 35 δ to 45 δ.

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 2700-2760cm^-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 ¹³CNMR, carbons in double bond which are sp2 hybridized absorb from 110 to 220 δ. Saturated aldehydes and ketones usually absorb in the region from 200 to 215 δ While aromatic and unsaturated carbonyl compounds absorb in the 190 to 200 δ region. The primary alkyl carbon absorbs in the range 10-15δ, a secondary alkyl radical in the range 16-25δ while a tertiary alkyl in the range 25-35 δ.

To propose:

A structure for the compound A, C₈H₁₀O₂, with the following spectral data.

IR: 1750 cm^-1; ¹³CNMR: 219 δ (20), two signals between 35 δ to 45 δ.

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 19.SE, Problem 70AP

Interpretation Introduction