(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 NA D + 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. 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. Figure 1 Conclusion: The product formed in the given reaction including stereochemistry is shown in Figure 1.

Question

Want to see the full answer?

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 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.

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.

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 3−ketobutanoyl 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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

None

Transmitance 3. Which one of the following compounds corresponds to this IR spectrum? Point out the absorption band(s) that helped you decide. OH H3C OH H₂C CH3 H3C CH3 H3C INFRARED SPECTRUM 0.8- 0.6 0.4- 0.2 3000 2000 1000 Wavenumber (cm-1) 4. Consider this compound: H3C On the structure above, label the different types of H's as A, B, C, etc. In table form, list the labeled signals, and for each one state the number of hydrogens, their shifts, and the splitting you would observe for these hydrogens in the ¹H NMR spectrum. Label # of hydrogens splitting Shift (2)

None

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 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.

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.

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 3−ketobutanoyl 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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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 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.

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.

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 3−ketobutanoyl 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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See 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 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.

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.

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 3−ketobutanoyl 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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

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.

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.

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 3−ketobutanoyl 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.

Answer 6

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.

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.

Figure 1

Conclusion:

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

Answer 7

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.

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.

Figure 1

Conclusion:

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

Answer 8

Interpretation Introduction

(b)

Interpretation:

The relative positions of NADPH and the 3−ketobutanoyl 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.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The relative positions of NADPH and the 3−ketobutanoyl 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.

Answer 10

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.

Answer 11

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.

Answer 12

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 15

Ch. 19 - Prob. 19.1P Ch. 19 - Prob. 19.2P Ch. 19 - Prob. 19.3P Ch. 19 - Prob. 19.4P Ch. 19 - Prob. 19.5P Ch. 19 - Prob. 19.6P Ch. 19 - Prob. 19.7P Ch. 19 - Prob. 19.8P Ch. 19 - Prob. 19.9P Ch. 19 - Prob. 19.10P

Concept explainers

Want to see the full answer?

Chapter 19 Solutions