Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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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.

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.

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.

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