ORGANIC CHEMISTRY (LOOSELEAF)
ORGANIC CHEMISTRY (LOOSELEAF)
6th Edition
ISBN: 9781260475630
Author: SMITH
Publisher: MCG
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Chapter 21, Problem 30P

Draw enol tautomer(s) for each compound. Ignore stereoisomers.

Chapter 21, Problem 30P, 23.29 Draw enol tautomer(s) for each compound. Ignore stereoisomers.

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Interpretation Introduction

(a)

Interpretation: Enol tautomer(s) of the given compound is to be drawn.

Concept introduction: Tautomers are the isomers which differ only in the position of the hydrogens and electrons of electronegative element, generally oxygen. There is no change in the carbon skeleton of the compound. This phenomenon which involves simple proton transfer in an intramolecular fashion is known as tautomerism.

The very common example of tautomerism is Keto-enol tautomerism. It can be acid or base catalysed.

Answer to Problem 30P

. The enol tautomer of this compound is shown below:

ORGANIC CHEMISTRY (LOOSELEAF), Chapter 21, Problem 30P , additional homework tip  1

Explanation of Solution

Tautomers are isomers which differ only in the position of the protons and electrons of the compound. There is no change in the carbon skeleton of the compound. The ball and stick model as shown in Figure 1.

ORGANIC CHEMISTRY (LOOSELEAF), Chapter 21, Problem 30P , additional homework tip  2

Figure 1

The enol tautomer of this compound is shown in Figure 2.

ORGANIC CHEMISTRY (LOOSELEAF), Chapter 21, Problem 30P , additional homework tip  3

Figure 2

Conclusion

The tautomer of the given compound is showed in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: Enol tautomer(s) of the given compound is to be drawn.

Concept introduction:

Tautomers are the isomers which differ only in the position of the hydrogens and electrons of electronegative element, generally oxygen. There is no change in the carbon skeleton of the compound. This phenomenon which involves simple proton transfer in an intramolecular fashion is known as tautomerism.

The very common example of tautomerism is Keto-enol tautomerism. It can be acid or base catalysed.

Answer to Problem 30P

. The enol tautomer of this compound is shown below:

ORGANIC CHEMISTRY (LOOSELEAF), Chapter 21, Problem 30P , additional homework tip  4

Explanation of Solution

Tautomers are isomers which differ only in the position of the protons and electrons of the compound. There is no change in the carbon skeleton of the compound. The ball and stick model as shown in Figure 3.

ORGANIC CHEMISTRY (LOOSELEAF), Chapter 21, Problem 30P , additional homework tip  5

Figure 3

The enol tautomer of this compound is shown in Figure 4.

ORGANIC CHEMISTRY (LOOSELEAF), Chapter 21, Problem 30P , additional homework tip  6

Figure 4

Conclusion

The tautomer of the given compound is showed in Figure 4.

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