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

Propose a structural formula for compound A, C5H13N, given its IR and calculated 1H-NMR spectra.

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Propose a structural formula for compound A, C5H13N, given its IR and calculated 1H-NMR spectra.

Compound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.

Compound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound.

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