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

Use diagram to answer the following: 1.Is the overall rxn endo- or exothermic. Explain briefly your answer____________________2. How many steps in this mechanism?_____________3. Which is the rate determining step? Explain briefly your answer____________________4. Identify (circle and label) the reactants,the products and intermediate (Is a Cation, Anion, or a Radical?) Please explain and provide full understanding.

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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Use diagram to answer the following: 1.Is the overall rxn endo- or exothermic. Explain briefly your answer____________________2. How many steps in this mechanism?_____________3. Which is the rate determining step? Explain briefly your answer____________________4. Identify (circle and label) the reactants,the products and intermediate (Is a Cation, Anion, or a Radical?) Please explain and provide full understanding.

Draw the entire mechanism and add Curved Arrows to show clearly how electrons areredistributed in the process. Please explain and provide steps clearly.

15) Create Lewis structure Br Br

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