a) Interpretation: How mass spectrometry is useful in distinguishing between 3-methyl-2-hexanone and 4-methyl-2-hexanone is to be stated. Concept introduction: In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene . The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation. To state: How to distinguish between 3-methyl-2-hexanone and 4-methyl-2-hexanone using mass spectrometry.

Question

The following compounds undergo McLafferty rearrangement in the mass spectrometer. Predict the masses of theresulting charged fragments. ) 4-methylhexan-2-one

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 19.14, Problem 25P

Interpretation Introduction

a)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-methyl-2-hexanone and 4-methyl-2-hexanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-methyl-2-hexanone and 4-methyl-2-hexanone using mass spectrometry.

Interpretation Introduction

b)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-heptanone and 4-heptanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-heptanone and 4-heptanone using mass spectrometry.

Interpretation Introduction

c)

Interpretation:

How mass spectrometry is useful in distinguishing between 2-methylpentanal and 3-methylpentanal is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To show:

How to distinguish between 2-methylpentanal and 3-methylpentanal using mass spectrometry.

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The following compounds undergo McLafferty rearrangement in the mass spectrometer. Predict the masses of theresulting charged fragments. ) 4-methylhexan-2-one

The following compounds undergo McLafferty rearrangement in the mass spectrometer. Predict the masses of the resulting charged fragments. (a) pentanal (b) 3-methylhexan-2-one (c) 4-methylhexan-2-one

From the following 1H-NMR and 13C-NMR spectra, assign a structure for a compound with a formula of C4H9Br:

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 19.14, Problem 25P

Interpretation Introduction

a)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-methyl-2-hexanone and 4-methyl-2-hexanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-methyl-2-hexanone and 4-methyl-2-hexanone using mass spectrometry.

Interpretation Introduction

b)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-heptanone and 4-heptanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-heptanone and 4-heptanone using mass spectrometry.

Interpretation Introduction

c)

Interpretation:

How mass spectrometry is useful in distinguishing between 2-methylpentanal and 3-methylpentanal is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To show:

How to distinguish between 2-methylpentanal and 3-methylpentanal using mass spectrometry.

Expert Solution & Answer

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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 19.14, Problem 25P

Interpretation Introduction

a)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-methyl-2-hexanone and 4-methyl-2-hexanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-methyl-2-hexanone and 4-methyl-2-hexanone using mass spectrometry.

Interpretation Introduction

b)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-heptanone and 4-heptanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-heptanone and 4-heptanone using mass spectrometry.

Interpretation Introduction

c)

Interpretation:

How mass spectrometry is useful in distinguishing between 2-methylpentanal and 3-methylpentanal is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To show:

How to distinguish between 2-methylpentanal and 3-methylpentanal using mass spectrometry.

Expert Solution & Answer

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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 19.14, Problem 25P

Interpretation Introduction

a)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-methyl-2-hexanone and 4-methyl-2-hexanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-methyl-2-hexanone and 4-methyl-2-hexanone using mass spectrometry.

Interpretation Introduction

b)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-heptanone and 4-heptanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-heptanone and 4-heptanone using mass spectrometry.

Interpretation Introduction

c)

Interpretation:

How mass spectrometry is useful in distinguishing between 2-methylpentanal and 3-methylpentanal is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To show:

How to distinguish between 2-methylpentanal and 3-methylpentanal using mass spectrometry.

Expert Solution & Answer

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Answer 5

Chapter 19.14, Problem 25P

Interpretation Introduction

a)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-methyl-2-hexanone and 4-methyl-2-hexanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-methyl-2-hexanone and 4-methyl-2-hexanone using mass spectrometry.

Interpretation Introduction

b)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-heptanone and 4-heptanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-heptanone and 4-heptanone using mass spectrometry.

Interpretation Introduction

c)

Interpretation:

How mass spectrometry is useful in distinguishing between 2-methylpentanal and 3-methylpentanal is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To show:

How to distinguish between 2-methylpentanal and 3-methylpentanal using mass spectrometry.

Answer 6

Chapter 19.14, Problem 25P

Interpretation Introduction

a)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-methyl-2-hexanone and 4-methyl-2-hexanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-methyl-2-hexanone and 4-methyl-2-hexanone using mass spectrometry.

Answer 7

Chapter 19.14, Problem 25P

Interpretation Introduction

a)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-methyl-2-hexanone and 4-methyl-2-hexanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-methyl-2-hexanone and 4-methyl-2-hexanone using mass spectrometry.

Answer 8

Interpretation Introduction

b)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-heptanone and 4-heptanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-heptanone and 4-heptanone using mass spectrometry.

Answer 9

Interpretation Introduction

b)

Interpretation:

How mass spectrometry is useful in distinguishing between 3-heptanone and 4-heptanone is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To state:

How to distinguish between 3-heptanone and 4-heptanone using mass spectrometry.

Answer 10

Interpretation Introduction

c)

Interpretation:

How mass spectrometry is useful in distinguishing between 2-methylpentanal and 3-methylpentanal is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To show:

How to distinguish between 2-methylpentanal and 3-methylpentanal using mass spectrometry.

Answer 11

Interpretation Introduction

c)

Interpretation:

How mass spectrometry is useful in distinguishing between 2-methylpentanal and 3-methylpentanal is to be stated.

Concept introduction:

In the mass spectrum of organic compounds, normally peaks due to Mc Lafferty rearrangement and α cleavage are generally visible. In Mc Lafferty rearrangement, aldehydes and ketones that have hydrogens on the γ carbons transfer the hydrogen on the carbon to the carbonyl oxygen and the bond between the α and β carbons is broken to yield an alkene. The charge remains with the oxygen containing fragment. In the α cleavage, the bond between the carbonyl carbon and the α carbon breaks to yield a neutral radical and a resaonance stabilized acyl cation.

To show:

How to distinguish between 2-methylpentanal and 3-methylpentanal using mass spectrometry.

Answer 12

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Answer 13

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Answer 23

Ch. 19.1 - Prob. 1P Ch. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3P Ch. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7P Ch. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9P Ch. 19.8 - Show the products you would obtain by...

Solution Summary: The author explains how mass spectrometry is useful in distinguishing between 3-methyl-2-hexanone and 4-methyl-2. The two compounds can be distinguished by the peaks observed due to Mc Lafferty rearrange

Chapter 19 Solutions