Organic Chemistry Study Guide and Solutions
Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
Question
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Chapter 5, Problem 5.32AP
Interpretation Introduction

(a)

Interpretation:

The preparation of the given compound from the alkene and other reagents is to be stated.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as CnH2n. They give rise to geometrical and stereoisomers- cistrans or EZ configuration.

The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 5.32AP

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  1

The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  2

Explanation of Solution

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  3

Figure 1

The alkene 3ethylpent2ene undergoes oxymercuration-reduction reaction in the presence of Hg(OAc)2 followed by NaBH4,NaOH results in the formation of the addition product 3ethylpentan3ol. The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  4

Figure 2

Conclusion

The preparation of the given compound from the alkene and other reagents is shown in Figure 2.

Interpretation Introduction

(b)

Interpretation:

The preparation of the given compound from the alkene with and other reagents is to be stated.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as CnH2n. They give rise to geometrical and stereoisomers- cistrans or EZ configuration.

The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name

Expert Solution
Check Mark

Answer to Problem 5.32AP

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  5

The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  6

Explanation of Solution

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  7

Figure 3

The alkene hex1ene undergoes hydroboration oxidation reaction in presence BH3 followed by NaBH4,NaOH results in the formation of the addition product hexanol. The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  8

Figure 4

Conclusion

The preparation of the given compound from the alkene and other reagents is shown in Figure 4.

Interpretation Introduction

(c)

Interpretation:

The preparation of the given compound from the alkene and other reagents is to be stated.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as CnH2n. They give rise to geometrical and stereoisomers- cistrans or EZ configuration.

The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 5.32AP

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  9

The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  10

Explanation of Solution

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  11

Figure 5

The alkene pent1ene reacts with HBr in presence of peroxide follows Anti-Markovnikov rule and forms bromopentane as the addition product. The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  12

Figure 6

Conclusion

The preparation of the given compound from the alkene and other reagents is shown in Figure 6.

Interpretation Introduction

(d)

Interpretation:

The preparation of the given compound from the alkene and other reagents is to be stated.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as CnH2n. They give rise to geometrical and stereoisomers- cistrans or EZ configuration.

The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 5.32AP

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  13

The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  14

Explanation of Solution

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  15

Figure 7

The alkene 3methylenepentane reacts with Br2 water and it result in the formation of 3bromopentan3ol addition product. The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  16

Figure 8

Conclusion

The preparation of the given compound from the alkene and other reagents is shown in Figure 8.

Interpretation Introduction

(e)

Interpretation:

The preparation of the given compound from the alkene and other reagents is to be stated.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as CnH2n. They give rise to geometrical and stereoisomers- cistrans or EZ configuration.

The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 5.32AP

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  17

The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  18

Explanation of Solution

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  19

Figure 9

The alkene 3methylpent2ene reacts with Br2 in presence of CCl4 result in the formation of dibromo substituted product 2,3dibromo3methylpentane The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  20

Figure 10

Conclusion

The preparation of the given compound from the alkene and other reagents is shown in Figure 10.

Interpretation Introduction

(f)

Interpretation:

The preparation of the given compound from the alkene and other reagents is to be stated.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as CnH2n. They give rise to geometrical and stereoisomers- cistrans or EZ configuration.

The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 5.32AP

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  21

The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  22

Explanation of Solution

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  23

Figure 11

The alkene 1methylcyclohex1ene undergoes ozonolysis reaction followed by reduction reaction with dimethyl sulfide. It results in the formation of 1,6 dicarbonyl compound. The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  24

Figure 12

Conclusion

The preparation of the given compound from the alkene and other reagents is shown in Figure 12.

Interpretation Introduction

(g)

Interpretation:

The preparation of the given compound from the alkene and other reagents is to be stated.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as CnH2n. They give rise to geometrical and stereoisomers- cistrans or EZ configuration.

The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 5.32AP

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  25

The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  26

Explanation of Solution

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  27

Figure 13

The alkene cyclopentene undergoes ozonolysis reaction followed by oxidation reaction in presence of H2O2/NaOH It results in the formation of glutaric acid. The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  28

Figure 14

Conclusion

The preparation of the given compound from the alkene and other reagents is shown in Figure 14.

Interpretation Introduction

(h)

Interpretation:

The preparation of the given compound from the alkene and other reagents is to be stated.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as CnH2n. They give rise to geometrical and stereoisomers- cistrans or EZ configuration.

The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 5.32AP

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  29

The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  30

Explanation of Solution

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  31

Figure 15

The alkene pent1ene undergoes addition reaction with HBr. It results in the formation of addition product 2bromopentane. The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  32

Figure 16

Conclusion

The preparation of the given compound from the alkene and other reagentsis shown in Figure 16.

Interpretation Introduction

(i)

Interpretation:

The preparation of the given compound from the alkene and other reagents is to be stated.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as CnH2n. They give rise to geometrical and stereoisomers- cistrans or EZ configuration.

The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name.

Expert Solution
Check Mark

Answer to Problem 5.32AP

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  33

The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  34

Explanation of Solution

The alkene which is used to synthesize the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  35

Figure 17

The alkene 3ethylpent2ene undergoes hydrogenation reaction in presence of H2, Pd/C results in the formation of 3ethylpentane. The synthesis of the given compound is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 5, Problem 5.32AP , additional homework tip  36

Figure 18

Conclusion

The preparation of the given compound from the alkene and other reagents is shown in Figure 18.

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Students have asked these similar questions
Give the systematic (IUPAC) names of the following alkenes. (а) СH— CH— CH— CH(CH3)2 (b) CH3(CH2)3¬C-CH2CH3 CH2 (c) CH2=CH-CH,–CH=CH2 (d) CH, —С—CH—CH—СH, CH3 (е) (f) (g) CH3 CH2 CH3 (h) .CH3 (j)
Compounds B and C are hydrocarbons with the structural formulae as shown below. CH, „CH, в (a) Name compounds B and C according to the IUPAC nomenclature. (b) Both B and C can undergo oxidation reaction with the same oxidizing agent. Write chemical equations involved and explain the differences between these two reactions. (c) Name one reaction that converts B to methylcyclohexane.
Draw a structural formula of an alkene that undergoes acid-catalyzed hydration to give each alcohol as the major product (more than one alkene may give each alcohol as the major product). (a) 3-Hexanol (b) 1-Methylcyclobutanol (c) 2-Methyl-2-butanol (d) 2-Propanol
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