Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 23, Problem 23.1P

Draw the enol or keto tautomer(s) of each compound.

a. Chapter 23, Problem 23.1P, Problem 23.1 Draw the enol or keto tautomer(s) of each compound.
		a. 		c. e. 
		b. d. f. [Draw mono , example  1 c. Chapter 23, Problem 23.1P, Problem 23.1 Draw the enol or keto tautomer(s) of each compound.
		a. 		c. e. 
		b. d. f. [Draw mono , example  2e. Chapter 23, Problem 23.1P, Problem 23.1 Draw the enol or keto tautomer(s) of each compound.
		a. 		c. e. 
		b. d. f. [Draw mono , example  3

b. Chapter 23, Problem 23.1P, Problem 23.1 Draw the enol or keto tautomer(s) of each compound.
		a. 		c. e. 
		b. d. f. [Draw mono , example  4d. Chapter 23, Problem 23.1P, Problem 23.1 Draw the enol or keto tautomer(s) of each compound.
		a. 		c. e. 
		b. d. f. [Draw mono , example  5f. Chapter 23, Problem 23.1P, Problem 23.1 Draw the enol or keto tautomer(s) of each compound.
		a. 		c. e. 
		b. d. f. [Draw mono , example  6[Draw mono enol

tautomers only]

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The enol or keto tautomer of the given compound is to be drawn.

Concept introduction: The chemical equilibrium that exists between a keto form of a compound and an enol form of the same compound is known as keto-enol tautomerism. Tautomers refer to these keto and enol forms. The keto-enol tautomerism takes place only if the acidic hydrogen is present at the αcarbon atom.

Answer to Problem 23.1P

The enol or keto tautomer of the given compound is shown below.

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  1

Explanation of Solution

The enol or keto tautomer of the given compound is shown as,

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  2

Figure 1

The keto form of the given enol form of a compound is shown appropriately because it contains the acidic hydrogen is present at the αcarbon atom.

Conclusion

The enol or keto tautomer of the given compound is shown in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The enol or keto tautomer of the given compound is to be drawn.

Concept introduction: The chemical equilibrium that exists between a keto form of a compound and an enol form of the same compound is known as keto-enol tautomerism. Tautomers refer to these keto and enol forms. The keto-enol tautomerism takes place only if the acidic hydrogen is present at the αcarbon atom.

Answer to Problem 23.1P

The enol or keto tautomer of the given compound is shown below.

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  3

Explanation of Solution

The enol or keto tautomer of the given compound is shown as,

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  4

Figure 2

The enol form of the given keto form of a compound is shown appropriately because it contains the acidic hydrogen is present at the αcarbon atom.

Conclusion

The enol or keto tautomer of the given compound is shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The enol or keto tautomer of the given compound is to be drawn.

Concept introduction: The chemical equilibrium that exists between a keto form of a compound and an enol form of the same compound is known as keto-enol tautomerism. Tautomers refer to these keto and enol forms. The keto-enol tautomerism takes place only if the acidic hydrogen is present at the αcarbon atom.

Answer to Problem 23.1P

The enol or keto tautomer of the given compound is shown below.

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  5

Explanation of Solution

The enol or keto tautomer of the given compound is shown as,

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  6

Figure 3

The enol form of the given keto form of a compound is shown appropriately because it contains the acidic hydrogen is present at the αcarbon atom.

Conclusion

The enol or keto tautomer of the given compound is shown in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The enol or keto tautomer of the given compound is to be drawn.

Concept introduction: The chemical equilibrium that exists between a keto form of a compound and an enol form of the same compound is known as keto-enol tautomerism. Tautomers refer to these keto and enol forms. The keto-enol tautomerism takes place only if the acidic hydrogen is present at the αcarbon atom.

Answer to Problem 23.1P

The enol or keto tautomer of the given compound is shown below.

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  7

Explanation of Solution

The enol or keto tautomer of the given compound is shown as,

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  8

Figure 4

The keto form of the given enol form of a compound is shown appropriately because it contains the acidic hydrogen is present at the αcarbon atom.

Conclusion

The enol or keto tautomer of the given compound is shown in Figure 4.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The enol or keto tautomer of the given compound is to be drawn.

Concept introduction: The chemical equilibrium that exists between a keto form of a compound and an enol form of the same compound is known as keto-enol tautomerism. Tautomers refer to these keto and enol forms. The keto-enol tautomerism takes place only if the acidic hydrogen is present at the αcarbon atom.

Answer to Problem 23.1P

The enol or keto tautomer of the given compound is shown below.

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  9

Explanation of Solution

The enol or keto tautomer of the given compound is shown as,

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  10

Figure 5

The enol form of the given keto form of a compound is shown appropriately because it contains the acidic hydrogen is present at the αcarbon atom.

Conclusion

The enol or keto tautomer of the given compound is shown in Figure 5.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The enol or keto tautomer of the given compound is to be drawn.

Concept introduction: The chemical equilibrium that exists between a keto form of a compound and an enol form of the same compound is known as keto-enol tautomerism. Tautomers refer to these keto and enol forms. The keto-enol tautomerism takes place only if the acidic hydrogen is present at the αcarbon atom.

Answer to Problem 23.1P

The enol or keto tautomer of the given compound is shown below.

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  11

Explanation of Solution

The enol or keto tautomer of the given compound is shown as,

Organic Chemistry, Chapter 23, Problem 23.1P , additional homework tip  12

Figure 6

The enol form of the given keto form of a compound is shown appropriately because it contains the acidic hydrogen is present at the αcarbon atom.

Conclusion

The enol or keto tautomer of the given compound is shown in Figure 6.

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Chapter 23 Solutions

Organic Chemistry

Ch. 23 - Prob. 23.11PCh. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Prob. 23.21PCh. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.23PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - Draw enol tautomers for each compound. a. b. c.Ch. 23 - Prob. 23.33PCh. 23 - What hydrogen atoms in each compound have a pKa25?...Ch. 23 - Rank the labeled protons in each compound in order...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - Prob. 23.41PCh. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - Draw a stepwise mechanism for each reaction. a. b.Ch. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Use the malonic ester synthesis to prepare each...Ch. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - Synthesize each compound from diethyl malonate....Ch. 23 - Prob. 23.49PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Synthesize each compound from ethyl acetoacetate....Ch. 23 - Draw the organic products formed in each reaction....Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.54PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Explain why each of the following reactions will...Ch. 23 - Prob. 23.58PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.61PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.63PCh. 23 - Prob. 23.64PCh. 23 - Convert acetophenone (C6H5COCH3) into each of the...Ch. 23 - Prob. 23.66PCh. 23 - Prob. 23.67PCh. 23 - Prob. 23.68PCh. 23 - Synthesize each product from ethyl acetoacetate...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.74PCh. 23 - Prob. 23.75PCh. 23 - Prob. 23.76PCh. 23 - Prob. 23.77PCh. 23 - Prob. 23.78P
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