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

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 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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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 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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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