(a) Interpretation: The reason as to why ionization of a π electron requires less energy than ionization of a σ electron is to be stated. Concept introduction: Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency.

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Answer 1

Question

Chapter 12, Problem 12.44AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why ionization of a π electron requires less energy than ionization of a σ electron is to be stated.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency.

Interpretation Introduction

(b)

Interpretation:

The structure of the molecular ion of 1-heptene formed by ionization of a π electron is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism that shows the conversion of the molecular ion of 1-heptene into the allyl cation is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

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1 (c) 2-Methyl-3-pentanol reacts with PCC to form compound F. (i) Draw the structure of F. (ii) In the mass spectrum, identify the m/z value of the molecular ion peak for compound F. (ii) Fragmentation of radical cation F exhibits two fragment ion peaks at m/z 57 and m/z 71. Propose the structures of these two fragments. (iv) Draw the resonance structure for each of the cation in (iii).

Account for the following observations: (a) The 1H NMR spectrum of cyclohexane shows a single peak at room temperature, but when the temperate is lowered significantly the peak starts to broaden and then separates into two. (b) At room temperature, the 19F NMR spectrum of PF5 shows two lines, and even at the lowest experimentally accessible temperatures the spectrum is substantially unchanged. (c) In the 1H NMR spectrum of a casually prepared sample of ethanol a triplet and a quartet are seen. These multiplets show additional splittings if the sample is prepared with the careful exclusion of water.

2,3-Dimethylbutane and 2,2-dimethylbutane have the same molecular ion in the mass spectrum, but only one of these isomers gives a significant fragment at m/z = 57. (a) Which isomer shows an intense peak at m/z = 57? (b) Propose a structure for the ion that gives rise to this peak. (c) The base peak in the mass spectrum of the other isomer occurs at m/z = 43. What ion gives rise to this peak?

Answer 2

Question

Chapter 12, Problem 12.44AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why ionization of a π electron requires less energy than ionization of a σ electron is to be stated.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency.

Interpretation Introduction

(b)

Interpretation:

The structure of the molecular ion of 1-heptene formed by ionization of a π electron is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism that shows the conversion of the molecular ion of 1-heptene into the allyl cation is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

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Answer 3

Question

Chapter 12, Problem 12.44AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why ionization of a π electron requires less energy than ionization of a σ electron is to be stated.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency.

Interpretation Introduction

(b)

Interpretation:

The structure of the molecular ion of 1-heptene formed by ionization of a π electron is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism that shows the conversion of the molecular ion of 1-heptene into the allyl cation is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

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Answer 4

Question

Chapter 12, Problem 12.44AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why ionization of a π electron requires less energy than ionization of a σ electron is to be stated.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency.

Interpretation Introduction

(b)

Interpretation:

The structure of the molecular ion of 1-heptene formed by ionization of a π electron is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism that shows the conversion of the molecular ion of 1-heptene into the allyl cation is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

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Answer 5

Chapter 12, Problem 12.44AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why ionization of a π electron requires less energy than ionization of a σ electron is to be stated.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency.

Interpretation Introduction

(b)

Interpretation:

The structure of the molecular ion of 1-heptene formed by ionization of a π electron is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism that shows the conversion of the molecular ion of 1-heptene into the allyl cation is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

Answer 6

Chapter 12, Problem 12.44AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why ionization of a π electron requires less energy than ionization of a σ electron is to be stated.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency.

Answer 7

Chapter 12, Problem 12.44AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why ionization of a π electron requires less energy than ionization of a σ electron is to be stated.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The structure of the molecular ion of 1-heptene formed by ionization of a π electron is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The structure of the molecular ion of 1-heptene formed by ionization of a π electron is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism that shows the conversion of the molecular ion of 1-heptene into the allyl cation is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism that shows the conversion of the molecular ion of 1-heptene into the allyl cation is to be drawn.

Concept introduction:

Each group in a compound exhibits a characteristic fragmentation pattern that help to analyze its mass spectrum. The peak of each and every fragment is observed at different frequency. Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 12 - Prob. 12.1P Ch. 12 - Prob. 12.2P Ch. 12 - Prob. 12.3P Ch. 12 - Prob. 12.4P Ch. 12 - Prob. 12.5P Ch. 12 - Prob. 12.6P Ch. 12 - Prob. 12.7P Ch. 12 - Prob. 12.8P Ch. 12 - Prob. 12.9P Ch. 12 - Prob. 12.10P

Solution Summary: The author explains the reason why ionization of a electron requires less energy. The peak of each and every fragment is observed at different frequency.

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Chapter 12 Solutions