The name of the reactants and products used in the reaction to activate acetoacetate before being used as a fuel has to be determined. Concept introduction: Acetoacetate is a ketone body generated in the mitochondria of the liver cells during ketogenesis. It is the first ketone body to be formed in the body, by the cleavage of a molecule of HMG-CoA The other two ketone bodies, β-hydroxybutyrate and acetone are derived from it. While β-hydroxybutyrate is formed by the reduction of a molecule of acetoacetate by NADH in the liver, acetone is formed by the loss of a carboxyl group from a molecule of acetoacetate in the bloodstream.

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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 25, Problem 25.73EP

Interpretation Introduction

Interpretation:

The name of the reactants and products used in the reaction to activate acetoacetate before being used as a fuel has to be determined.

Concept introduction:

Acetoacetate is a ketone body generated in the mitochondria of the liver cells during ketogenesis. It is the first ketone body to be formed in the body, by the cleavage of a molecule of HMG-CoA The other two ketone bodies, β-hydroxybutyrate and acetone are derived from it. While β-hydroxybutyrate is formed by the reduction of a molecule of acetoacetate by NADH in the liver, acetone is formed by the loss of a carboxyl group from a molecule of acetoacetate in the bloodstream.

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Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)

3. What starting material would you use to synthesize 3-hydroxypentanoic acid using a NaBH4 reduction?

1. Give stereochemical (Fischer projection) formulas for all (but no extras) the stereoisomers that could theoretically form during the reduction of a. the carbonyl group of 2-methyl-3--pentanone b. both carbonyl groups of 2,4-pentanedione (careful!) 2. Predict the products of the reduction of O=CCH2CH2CH2C=O with a. LiAlH4 b. NaBH4 CH3 OH

Answer 2

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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 25, Problem 25.73EP

Interpretation Introduction

Interpretation:

The name of the reactants and products used in the reaction to activate acetoacetate before being used as a fuel has to be determined.

Concept introduction:

Acetoacetate is a ketone body generated in the mitochondria of the liver cells during ketogenesis. It is the first ketone body to be formed in the body, by the cleavage of a molecule of HMG-CoA The other two ketone bodies, β-hydroxybutyrate and acetone are derived from it. While β-hydroxybutyrate is formed by the reduction of a molecule of acetoacetate by NADH in the liver, acetone is formed by the loss of a carboxyl group from a molecule of acetoacetate in the bloodstream.

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Answer 3

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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 25, Problem 25.73EP

Interpretation Introduction

Interpretation:

The name of the reactants and products used in the reaction to activate acetoacetate before being used as a fuel has to be determined.

Concept introduction:

Acetoacetate is a ketone body generated in the mitochondria of the liver cells during ketogenesis. It is the first ketone body to be formed in the body, by the cleavage of a molecule of HMG-CoA The other two ketone bodies, β-hydroxybutyrate and acetone are derived from it. While β-hydroxybutyrate is formed by the reduction of a molecule of acetoacetate by NADH in the liver, acetone is formed by the loss of a carboxyl group from a molecule of acetoacetate in the bloodstream.

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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 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 25, Problem 25.73EP

Interpretation Introduction