EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
bartleby

Concept explainers

Question
Book Icon
Chapter 19, Problem 19.57AP
Interpretation Introduction

(a)

Interpretation:

The product of the given reduction reaction including stereochemistry is to be shown.

Concept Introduction:

The compound NADH is a reducing agent. It is used in the biological reduction reactions. The NADH molecule gets converted to NAD+ molecule after reduction. Ketone contains the electrophilic carbonyl carbon center. The hydride ion attacks at the carbonyl carbon which results in the formation of alcohol.

Answer:

The product of the given reduction reaction including stereochemistry is shown below.

EBK ORGANIC CHEMISTRY, Chapter 19, Problem 19.57AP , additional homework tip  1

Explanation:

The enzyme 3-ketobutanoyl thioester reductase catalyzes the reduction of the ketone carbonyl group of the given compound with NADPH to give the R stereoisomer of the product. The compound NADPH provides the hydride ion for the reduction reaction. It attacks the ketone compound in stereospecific manner to form (R) alcohol product only. The product of given reaction including stereochemistry is shown below.

EBK ORGANIC CHEMISTRY, Chapter 19, Problem 19.57AP , additional homework tip  2

Figure 1

Conclusion:

The product formed in the given reaction including stereochemistry is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The relative positions of NADPH and the 3ketobutanoyl thioester molecules in the transition state is to be shown.

Concept Introduction:

The compound NADH is a reducing agent. It is used in the biological reduction reactions. The NADH molecule gets converted to NAD+ molecule after reduction. Ketone contains an electrophilic carbonyl carbon center. The hydride ion attacks at the carbonyl carbon which results in the formation of alcohol.

Interpretation Introduction

(c)

Interpretation:

The role of the side chain hydroxyl group of tyrosine and serine in this reaction is to be stated.

Concept Introduction:

The compound NADH is a reducing agent. It is used in the biological reduction reactions. The NADH molecule gets converted to NAD+ molecule after reduction. Ketone contains an electrophilic carbonyl carbon center. The hydride ion attacks at the carbonyl carbon which results in the formation of alcohol.

Blurred answer
Students have asked these similar questions
Complete the following esterification reactions by drawing the line formulas of the carboxylic acid and alcohol required to form the ester shown. catalyst catalyst catalyst apricot fragrance
Show the saponification products of the following ester: You don't need to draw in the Na+ cation. catalyst, A catalyst, A catalyst, A
What would happen if the carboxylic acid and alcohol groups were on the same molecule? In essence, the molecule reacts with itself. Draw the structure of the products formed in this manner using the reactants below. If two functional groups interact with one another on the same molecule, this is called an “intramolecular" (within one) rather than "intermolecular" (between two or more) attack. OH OH catalyst OH HO catalyst catalyst HO OH

Chapter 19 Solutions

EBK ORGANIC CHEMISTRY

Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning