General, Organic, and Biological Chemistry
General, Organic, and Biological Chemistry
7th Edition
ISBN: 9781285853918
Author: H. Stephen Stoker
Publisher: Cengage Learning
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Chapter 25, Problem 25.29EP

(a)

Interpretation Introduction

Interpretation: To determine the functional group change that occurs in step 1 of a turn of the βoxidation pathway.

Concept introduction: The βoxidation pathway is defined as a repetitive series of four biochemical reactions in which acyl CoA is degraded to acetyl CoA by the removal of two carbon atoms at a time. NADH and FADH2 are also produced in this pathway.

Functional groups are defined as the group of atoms which are attached to the carbon backbone of organic compounds. These are generally heteroatoms which are attached to the parent hydrocarbon chain. Some examples of functional groups are as follows:

General, Organic, and Biological Chemistry, Chapter 25, Problem 25.29EP , additional homework tip  1

Here, R and R' represent an alkyl group. In alkene, R1, R2, R3 , and R4 can be the same or different or can be hydrogen.

Alkanes are saturated hydrocarbons that contain covalently bonded hydrogen and carbon atoms.

(a)

Expert Solution
Check Mark

Answer to Problem 25.29EP

In step 1 of a turn of the βoxidation pathway, an alkane is converted to an alkene.

Explanation of Solution

The reaction in step 1 of a turn of the βoxidation pathway is a dehydrogenation reaction in which hydrogen atoms from the α and β carbons of acyl CoA are removed; a double bond is formed between α and β carbons. FAD oxidizes acyl CoA. This reaction is catalyzed by acyl CoA dehydrogenase enzyme. The reaction for step 1 is as follows:

General, Organic, and Biological Chemistry, Chapter 25, Problem 25.29EP , additional homework tip  2

Therefore, acyl CoA is converted to trans-enoyl CoA. The functional group in acyl CoA and trans-enoyl CoA are represented as follows:

General, Organic, and Biological Chemistry, Chapter 25, Problem 25.29EP , additional homework tip  3

Carbon atoms are bonded with other carbon atoms by a single covalent bond in acyl CoA, therefore; it is an alkane. A double bond is present in trans-enoyl CoA, therefore; it is an alkene. Hence, in step 1 of a turn of the βoxidation pathway, an alkane is converted to an alkene.

(b)

Interpretation Introduction

Interpretation: To determine the functional group change that occurs in step 2 of a turn of the βoxidation pathway.

Concept introduction: The βoxidation pathway is defined as a repetitive series of four biochemical reactions in which acyl CoA is degraded to acetyl CoA by the removal of two carbon atoms at a time. NADH and FADH2 are also produced in this pathway.

Functional groups are defined as the group of atoms which are attached to the carbon backbone of organic compounds. These are generally heteroatoms which are attached to the parent hydrocarbon chain. Some examples of functional groups are as follows:

General, Organic, and Biological Chemistry, Chapter 25, Problem 25.29EP , additional homework tip  4

Here, R and R' represent an alkyl group. In alkene, R1, R2, R3 , and R4 can be the same or different or can be hydrogen.

Alkanes are saturated hydrocarbons that contain covalently bonded hydrogen and carbon atoms. In secondary alcohol, the carbon atom of the hydroxyl group (OH) is bonded to alkyl groups on both sides.

(b)

Expert Solution
Check Mark

Answer to Problem 25.29EP

In step 2 of a turn of the βoxidation pathway, an alkene is converted to 2° alcohol.

Explanation of Solution

The reaction in step 2 of a turn of the βoxidation pathway is a hydration reaction. In step 2, a water (H2O) molecule is added across the trans double bond in trans-enoyl CoA, therefore; secondary alcohol is produced at β carbon. This reaction is catalyzed by enoyl CoA hydratase enzyme. The reaction for step 2 is as follows:

General, Organic, and Biological Chemistry, Chapter 25, Problem 25.29EP , additional homework tip  5

Therefore, acyl CoAtrans-enoyl CoA is converted to L-β-hydroxyacyl CoA. The functional group in trans-enoyl CoA and L-β-hydroxyacyl CoA are represented as follows:

General, Organic, and Biological Chemistry, Chapter 25, Problem 25.29EP , additional homework tip  6

A double bond is present in trans-enoyl CoA, therefore; it is an alkene. In L-β-hydroxyacyl CoA, the carbon atom of the hydroxyl group (OH) is bonded to alkyl groups on both sides. Hence, it is a 2° alcohol. Therefore, in step 2 of a turn of the βoxidation pathway, an alkene is converted to 2° alcohol.

(c)

Interpretation Introduction

Interpretation: To determine the functional group change that occurs in step 3 of a turn of the βoxidation pathway.

Concept introduction: The βoxidation pathway is defined as a repetitive series of four biochemical reactions in which acyl CoA is degraded to acetyl CoA by the removal of two carbon atoms at a time. NADH and FADH2 are also produced in this pathway.

Functional groups are defined as the group of atoms which are attached to the carbon backbone of organic compounds. These are generally heteroatoms which are attached to the parent hydrocarbon chain. Some examples of functional groups are as follows:

General, Organic, and Biological Chemistry, Chapter 25, Problem 25.29EP , additional homework tip  7

Here, R and R' represent an alkyl group. In alkene, R1, R2, R3 , and R4 can be the same or different or can be hydrogen.

Alkanes are saturated hydrocarbons that contain covalently bonded hydrogen and carbon atoms. In secondary alcohol, the carbon atom of the hydroxyl group (OH) is bonded to alkyl groups on either side.

(c)

Expert Solution
Check Mark

Answer to Problem 25.29EP

In step 3 of a turn of the βoxidation pathway, 2° alcohol is converted to a ketone.

Explanation of Solution

The reaction in step 3 of a turn of the βoxidation pathway is a dehydrogenation reaction in which two hydrogen atoms are removed from L-β-hydroxyacyl CoA. In this reaction, β-hydroxy group is converted to a keto group. NAD+ is used as an oxidizing agent. This reaction is catalyzed by β-hydroxyacyl CoA dehydrogenase enzyme. The reaction for step 3 is as follows:

General, Organic, and Biological Chemistry, Chapter 25, Problem 25.29EP , additional homework tip  8

Therefore, L-β-hydroxyacyl CoA is converted to β-ketoacyl CoA. The functional group in L-β-hydroxyacyl CoA and β-ketoacyl CoA are represented as follows:

General, Organic, and Biological Chemistry, Chapter 25, Problem 25.29EP , additional homework tip  9

In L-β-hydroxyacyl CoA, the carbon atom of the hydroxyl group (OH) is bonded to alkyl groups on both sides. Hence, it is a 2° alcohol. Carbonyl group in β-ketoacyl CoA is bonded to alkyl groups on both sides, hence; it is a keto compound. Therefore, in step 3 of a turn of the βoxidation pathway, 2° alcohol is converted to a keto group.

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Chapter 25 Solutions

General, Organic, and Biological Chemistry

Ch. 25.3 - Prob. 3QQCh. 25.4 - Prob. 1QQCh. 25.4 - Prob. 2QQCh. 25.4 - Prob. 3QQCh. 25.4 - Prob. 4QQCh. 25.4 - Prob. 5QQCh. 25.4 - Prob. 6QQCh. 25.5 - Prob. 1QQCh. 25.5 - Prob. 2QQCh. 25.5 - Prob. 3QQCh. 25.6 - Prob. 1QQCh. 25.6 - Prob. 2QQCh. 25.6 - Prob. 3QQCh. 25.6 - Prob. 4QQCh. 25.6 - Prob. 5QQCh. 25.6 - Prob. 6QQCh. 25.7 - Prob. 1QQCh. 25.7 - Prob. 2QQCh. 25.7 - Prob. 3QQCh. 25.7 - Prob. 4QQCh. 25.7 - The reducing agent needed in the process of...Ch. 25.7 - Prob. 6QQCh. 25.8 - Prob. 1QQCh. 25.8 - Prob. 2QQCh. 25.9 - Prob. 1QQCh. 25.9 - Prob. 2QQCh. 25.9 - Prob. 3QQCh. 25.9 - Prob. 4QQCh. 25.10 - Which of the following substances cannot be...Ch. 25.10 - Prob. 2QQCh. 25.10 - Which of the following processes occurs within the...Ch. 25.11 - Prob. 1QQCh. 25.11 - Prob. 2QQCh. 25.11 - Prob. 3QQCh. 25 - Indicate whether each of the following aspects of...Ch. 25 - Indicate whether each of the following aspects of...Ch. 25 - Indicate whether each of the following pairings of...Ch. 25 - Prob. 25.4EPCh. 25 - Indicate whether each of the following statements...Ch. 25 - Prob. 25.6EPCh. 25 - Prob. 25.7EPCh. 25 - What is a chylomicron?Ch. 25 - What are the products of the complete hydrolysis...Ch. 25 - What are the major products of the incomplete...Ch. 25 - Prob. 25.11EPCh. 25 - At what location are free fatty acids and...Ch. 25 - Prob. 25.13EPCh. 25 - Prob. 25.14EPCh. 25 - Prob. 25.15EPCh. 25 - Prob. 25.16EPCh. 25 - Prob. 25.17EPCh. 25 - Prob. 25.18EPCh. 25 - Prob. 25.19EPCh. 25 - Prob. 25.20EPCh. 25 - Prob. 25.21EPCh. 25 - Prob. 25.22EPCh. 25 - Prob. 25.23EPCh. 25 - Prob. 25.24EPCh. 25 - Prob. 25.25EPCh. 25 - Prob. 25.26EPCh. 25 - Prob. 25.27EPCh. 25 - Identify the oxidizing agent needed in Step 3 of a...Ch. 25 - Prob. 25.29EPCh. 25 - Prob. 25.30EPCh. 25 - Prob. 25.31EPCh. 25 - Prob. 25.32EPCh. 25 - Prob. 25.33EPCh. 25 - Prob. 25.34EPCh. 25 - Prob. 25.35EPCh. 25 - Prob. 25.36EPCh. 25 - Prob. 25.37EPCh. 25 - Prob. 25.38EPCh. 25 - Prob. 25.39EPCh. 25 - Prob. 25.40EPCh. 25 - Prob. 25.41EPCh. 25 - Prob. 25.42EPCh. 25 - How many turns of the -oxidation pathway would be...Ch. 25 - How many turns of the -oxidation pathway would be...Ch. 25 - Prob. 25.45EPCh. 25 - Prob. 25.46EPCh. 25 - Prob. 25.47EPCh. 25 - Prob. 25.48EPCh. 25 - Prob. 25.49EPCh. 25 - Explain why fatty acids cannot serve as fuel for...Ch. 25 - Prob. 25.51EPCh. 25 - Prob. 25.52EPCh. 25 - Prob. 25.53EPCh. 25 - Prob. 25.54EPCh. 25 - Prob. 25.55EPCh. 25 - Prob. 25.56EPCh. 25 - Prob. 25.57EPCh. 25 - Prob. 25.58EPCh. 25 - Prob. 25.59EPCh. 25 - Prob. 25.60EPCh. 25 - Prob. 25.61EPCh. 25 - Why does a deficiency of carbohydrates in the diet...Ch. 25 - Prob. 25.63EPCh. 25 - Prob. 25.64EPCh. 25 - Prob. 25.65EPCh. 25 - Prob. 25.66EPCh. 25 - Prob. 25.67EPCh. 25 - Prob. 25.68EPCh. 25 - Prob. 25.69EPCh. 25 - Prob. 25.70EPCh. 25 - Prob. 25.71EPCh. 25 - Prob. 25.72EPCh. 25 - Prob. 25.73EPCh. 25 - Prob. 25.74EPCh. 25 - Prob. 25.75EPCh. 25 - Severe ketosis situations produce acidosis....Ch. 25 - Prob. 25.77EPCh. 25 - Prob. 25.78EPCh. 25 - Prob. 25.79EPCh. 25 - Prob. 25.80EPCh. 25 - Prob. 25.81EPCh. 25 - Prob. 25.82EPCh. 25 - Prob. 25.83EPCh. 25 - Prob. 25.84EPCh. 25 - Prob. 25.85EPCh. 25 - Prob. 25.86EPCh. 25 - Prob. 25.87EPCh. 25 - Prob. 25.88EPCh. 25 - Prob. 25.89EPCh. 25 - Prob. 25.90EPCh. 25 - Prob. 25.91EPCh. 25 - Prob. 25.92EPCh. 25 - Prob. 25.93EPCh. 25 - Prob. 25.94EPCh. 25 - What role does molecular oxygen, O2, play in fatty...Ch. 25 - Prob. 25.96EPCh. 25 - Prob. 25.97EPCh. 25 - Prob. 25.98EPCh. 25 - Prob. 25.99EPCh. 25 - Prob. 25.100EPCh. 25 - Prob. 25.101EPCh. 25 - Prob. 25.102EPCh. 25 - Prob. 25.103EPCh. 25 - Prob. 25.104EPCh. 25 - Prob. 25.105EPCh. 25 - Prob. 25.106EPCh. 25 - Prob. 25.107EPCh. 25 - Prob. 25.108EPCh. 25 - Prob. 25.109EPCh. 25 - Prob. 25.110EPCh. 25 - Prob. 25.111EPCh. 25 - Prob. 25.112EPCh. 25 - Prob. 25.113EPCh. 25 - Prob. 25.114EP
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