The structure of the compound C 5 H 10 O has to be proposed. Concept introduction: NMR spectroscopy: It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1 H, 13 C, 15 N, 19 F and 31 P 1 H NMR : A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds. Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million). Chemical shift values for protons in different electronic environment: Types of protons Chemical shift Methyl ~0 .9 methylene ~1 .2 Methine ~1 .7 Allylic ~2 Alkynyl ~2 .5 Aromatic methyl ~2-5 Alkyl halide ~2-4 Alcohol ~ 2 − 5 Vinyl ~ 4.5 − 6.5 Aryl ~ 6.5 − 8 Aldehyde ~ 10 carboxylic ~ 12

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Answer 1

Question

Chapter 15, Problem 57PP

(a)

Interpretation Introduction

Interpretation:

The structure of the compound C5H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

(b)

Interpretation Introduction

Interpretation:

The structure of the compound C5H12O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

(c)

Interpretation Introduction

Interpretation:

The structure of the compound C4H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

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Answer 2

Question

Chapter 15, Problem 57PP

(a)

Interpretation Introduction

Interpretation:

The structure of the compound C5H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

(b)

Interpretation Introduction

Interpretation:

The structure of the compound C5H12O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

(c)

Interpretation Introduction

Interpretation:

The structure of the compound C4H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

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Answer 3

Question

Chapter 15, Problem 57PP

(a)

Interpretation Introduction

Interpretation:

The structure of the compound C5H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

(b)

Interpretation Introduction

Interpretation:

The structure of the compound C5H12O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

(c)

Interpretation Introduction

Interpretation:

The structure of the compound C4H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

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Answer 4

Question

Chapter 15, Problem 57PP

(a)

Interpretation Introduction

Interpretation:

The structure of the compound C5H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

(b)

Interpretation Introduction

Interpretation:

The structure of the compound C5H12O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

(c)

Interpretation Introduction

Interpretation:

The structure of the compound C4H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

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Answer 5

Chapter 15, Problem 57PP

(a)

Interpretation Introduction

Interpretation:

The structure of the compound C5H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

(b)

Interpretation Introduction

Interpretation:

The structure of the compound C5H12O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

(c)

Interpretation Introduction

Interpretation:

The structure of the compound C4H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

Answer 6

Chapter 15, Problem 57PP

(a)

Interpretation Introduction

Interpretation:

The structure of the compound C5H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

Answer 7

Chapter 15, Problem 57PP

(a)

Interpretation Introduction

Interpretation:

The structure of the compound C5H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

Answer 8

(b)

Interpretation Introduction

Interpretation:

The structure of the compound C5H12O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

Answer 9

(b)

Interpretation Introduction

Interpretation:

The structure of the compound C5H12O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

Answer 10

(c)

Interpretation Introduction

Interpretation:

The structure of the compound C4H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

Answer 11

(c)

Interpretation Introduction

Interpretation:

The structure of the compound C4H10O has to be proposed.

Concept introduction:

NMR spectroscopy:

It is the study of the interaction between electromagnetic radiation and the nuclei of atoms and the variety of nuclei studied includes 1H, 13C, 15N, 19F and 31P

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

Chemical shift: The frequency of the proton signal in the spectrum with reference to the standard compound which may be TMS(Tetramethylsilane) shows signal at 0 ppm(parts per million).

Chemical shift values for protons in different electronic environment:

Types of protons Chemical shift
Methyl ~0.9
methylene ~1.2
Methine ~1.7
Allylic ~2
Alkynyl ~2.5
Aromatic methyl ~2-5
Alkyl halide ~2-4

Alcohol ~2−5
Vinyl ~4.5−6.5

Aryl ~6.5−8
Aldehyde ~10
carboxylic ~12

Answer 12

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Answer 13

Expert Solution & Answer

Answer 14

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Answer 15

Ch. 15.4 - Prob. 1LTS Ch. 15.4 - Prob. 1PTS Ch. 15.4 - Prob. 2PTS Ch. 15.4 - Prob. 3PTS Ch. 15.4 - Prob. 4ATS Ch. 15.4 - Prob. 2LTS Ch. 15.4 - Prob. 5PTS Ch. 15.4 - Prob. 6PTS Ch. 15.4 - Carvone, a natural product isolated from plants,...Ch. 15.5 - Prob. 3LTS

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Chapter 15 Solutions

Types of protons	Chemical shift
Methyl	~0.9
methylene	~1.2
Methine	~1.7
Allylic	~2
Alkynyl	~2.5
Aromatic methyl	~2-5
Alkyl halide	~2-4