Among (a) acetoacetate (b) β-hydroxybutyrate(c) acetone the one which is not a ketone body has to be identified. Concept introduction: Ketone bodies are water-soluble molecules which are synthesized from acetyl CoA through the process of ketogenesis. Ketogenesis occurs in the mitochondria of the liver cells. The initial reactants are the molecules of acetyl CoA which are produced by the β-oxidation of fatty acid molecules. Ketone bodies are generally produced when the amount of acetyl CoA in the body is much larger than the amount of oxaloacetate. This happens due to the carbohydrate-lipid imbalance in the body caused by much smaller intake of food rich in carbohydrates, or inefficient processing of glucose by the body.

Question

Part I. a) Elucidate the structure of compound A using the following information. • mass spectrum: m+ = 102, m/2=57 312=29 • IR spectrum: 1002.5 % TRANSMITTANCE Ngg 50 40 30 20 90 80 70 60 MICRONS 5 8 9 10 12 13 14 15 16 19 1740 cm M 10 0 4000 3600 3200 2800 2400 2000 1800 1600 13 • CNMR 'H -NMR Peak 8 ppm (H) Integration multiplicity a 1.5 (3H) triplet b 1.3 1.5 (3H) triplet C 2.3 1 (2H) quartet d 4.1 1 (2H) quartet & ppm (c) 10 15 28 60 177 (C=0) b) Elucidate the structure of compound B using the following information 13C/DEPT NMR 150.9 MHz IIL 1400 WAVENUMBERS (CM-1) DEPT-90 DEPT-135 85 80 75 70 65 60 55 50 45 40 35 30 25 20 ppm 1200 1000 800 600 400

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 14.6, Problem 1QQ

Interpretation Introduction

Interpretation:

Among (a) acetoacetate (b) β-hydroxybutyrate(c) acetone the one which is not a ketone body has to be identified.

Concept introduction:

Ketone bodies are water-soluble molecules which are synthesized from acetyl CoA through the process of ketogenesis. Ketogenesis occurs in the mitochondria of the liver cells. The initial reactants are the molecules of acetyl CoA which are produced by the β-oxidation of fatty acid molecules. Ketone bodies are generally produced when the amount of acetyl CoA in the body is much larger than the amount of oxaloacetate. This happens due to the carbohydrate-lipid imbalance in the body caused by much smaller intake of food rich in carbohydrates, or inefficient processing of glucose by the body.

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Part I. a) Elucidate the structure of compound A using the following information. • mass spectrum: m+ = 102, m/2=57 312=29 • IR spectrum: 1002.5 % TRANSMITTANCE Ngg 50 40 30 20 90 80 70 60 MICRONS 5 8 9 10 12 13 14 15 16 19 1740 cm M 10 0 4000 3600 3200 2800 2400 2000 1800 1600 13 • CNMR 'H -NMR Peak 8 ppm (H) Integration multiplicity a 1.5 (3H) triplet b 1.3 1.5 (3H) triplet C 2.3 1 (2H) quartet d 4.1 1 (2H) quartet & ppm (c) 10 15 28 60 177 (C=0) b) Elucidate the structure of compound B using the following information 13C/DEPT NMR 150.9 MHz IIL 1400 WAVENUMBERS (CM-1) DEPT-90 DEPT-135 85 80 75 70 65 60 55 50 45 40 35 30 25 20 ppm 1200 1000 800 600 400

• Part II. a) Elucidate The structure of compound c w/ molecular formula C10 11202 and the following data below: • IR spectra % TRANSMITTANCE 1002.5 90 80 70 60 50 40 30 20 10 0 4000 3600 3200 2800 2400 2000 1800 1600 • Information from 'HAMR MICRONS 8 9 10 11 14 15 16 19 25 1400 WAVENUMBERS (CM-1) 1200 1000 800 600 400 peak 8 ppm Integration multiplicity a 2.1 1.5 (3H) Singlet b 3.6 1 (2H) singlet с 3.8 1.5 (3H) Singlet d 6.8 1(2H) doublet 7.1 1(2H) doublet Information from 13C-nmR Normal carbon 29ppm Dept 135 Dept -90 + NO peak NO peak 50 ppm 55 ppm + NO peak 114 ppm t 126 ppm No peak NO peak 130 ppm t + 159 ppm No peak NO peak 207 ppm по реак NO peak

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Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 14.6, Problem 1QQ

Interpretation Introduction

Interpretation:

Among (a) acetoacetate (b) β-hydroxybutyrate(c) acetone the one which is not a ketone body has to be identified.

Concept introduction:

Ketone bodies are water-soluble molecules which are synthesized from acetyl CoA through the process of ketogenesis. Ketogenesis occurs in the mitochondria of the liver cells. The initial reactants are the molecules of acetyl CoA which are produced by the β-oxidation of fatty acid molecules. Ketone bodies are generally produced when the amount of acetyl CoA in the body is much larger than the amount of oxaloacetate. This happens due to the carbohydrate-lipid imbalance in the body caused by much smaller intake of food rich in carbohydrates, or inefficient processing of glucose by the body.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 14.6, Problem 1QQ

Interpretation Introduction

Interpretation:

Among (a) acetoacetate (b) β-hydroxybutyrate(c) acetone the one which is not a ketone body has to be identified.

Concept introduction:

Ketone bodies are water-soluble molecules which are synthesized from acetyl CoA through the process of ketogenesis. Ketogenesis occurs in the mitochondria of the liver cells. The initial reactants are the molecules of acetyl CoA which are produced by the β-oxidation of fatty acid molecules. Ketone bodies are generally produced when the amount of acetyl CoA in the body is much larger than the amount of oxaloacetate. This happens due to the carbohydrate-lipid imbalance in the body caused by much smaller intake of food rich in carbohydrates, or inefficient processing of glucose by the body.

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Check out sample textbook solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 14.6, Problem 1QQ

Interpretation Introduction