Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
Question
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Chapter 20, Problem 20.47AP
Interpretation Introduction

(a)

Interpretation:

Synthesis of 2-pentanol from propanoic acid using appropriate reagents is to be stated.

Concept introduction:

Synthesis is the process of conversion of one compound into another using reagents. For the conversion of one compound into another, multiple number of steps undergoes using multiple reagents.

Expert Solution
Check Mark

Answer to Problem 20.47AP

Synthesis of 2-pentanol from propanoic acid using appropriate reagents is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  1

Explanation of Solution

The synthesis of 2-pentanol from propanoic acid is done using multiple steps shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  2

Figure 1

The total number of steps in the synthesis are five. In the first step propanoic acid is converted into acid chloride which is converted into ketone using Grignard’s reagent.

The ketone 2-butanone thus formed is brominated at the alpha position. Then the brominated product undergoes dehydrohalogenation in the presence of alcoholic KOH to give α,β- unsaturated ketone. The Michael addition of Gilman’s reagent on the α,β- unsaturated ketone 3-buten-2-one takes place to give the required product 2-pentanol.

Conclusion

Synthesis of 2-pentanol from propanoic acid using appropriate reagents is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the given compound from allyl alcohol using appropriate reagents is to be stated.

Concept introduction:

Synthesis is the process of conversion of one compound into another using reagents. For the conversion of one compound into another, the multiple numbers of steps undergo using multiple reagents.

Expert Solution
Check Mark

Answer to Problem 20.47AP

Synthesis of the given compound from allyl alcohol using appropriate reagents is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  3

Explanation of Solution

The given compound to be synthesized is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  4

Figure 2

The synthesis of the given compound from allyl alcohol is done using multiple steps shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  5

Figure 3

The allyl alcohol, prop-2-en-1-ol is reduced first of all to the propan-1-ol which is then oxidized to carboxylic acid propionic acid. The propionic acid then formed reacts with the allyl alcohol to give the required product.

Conclusion

Synthesis of the given compound from allyl alcohol using appropriate reagents is shown in Figure 3.

Interpretation Introduction

(c)

Interpretation:

Synthesis of 2-methylheptane from pentanoic acid using appropriate reagents is to be stated.

Concept introduction:

Synthesis is the process of conversion of one compound into another using reagents. For the conversion of one compound into another, the multiple numbers of steps undergo using multiple reagents.

Expert Solution
Check Mark

Answer to Problem 20.47AP

Synthesis of 2-methylheptane from pentanoic acid using appropriate reagents is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  6

Explanation of Solution

The synthesis of 2-methylheptane from pentanoic acid using appropriate reagents is done using multiple steps shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  7

Figure 4

The conversion of pentanoic acid to acid chloride is done by using thionyl chloride. The acid chloride thus produced is reacted with DIBAH at 78°C to give pentanal. The pentanal thus produced with a Grignard reagent to give 2-methyl-3-heptanol which is then dehydrated in the presence of concentrated acid to give an alkene 2-methyl-2-heptene. The 2-methyl-2-heptene is then reduced using catalytic hydrogenation to give the required product 2-methylheptane.

Conclusion

Synthesis of 2-methylheptane from pentanoic acid using appropriate reagents is shown in Figure 4.

Interpretation Introduction

(d)

Interpretation:

Synthesis of m-nitrobenzoicacid from toluene using appropriate reagents is to be stated.

Concept introduction:

Synthesis is the process of conversion of one compound into another using reagents. For the conversion of one compound into another, the multiple numbers of steps undergo using multiple reagents.

Expert Solution
Check Mark

Answer to Problem 20.47AP

Synthesis of m-nitrobenzoicacid from toluene using appropriate reagents is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  8

Explanation of Solution

The synthesis of m-nitrobenzoicacid from toluene using appropriate reagents is done using multiple steps shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  9

Figure 5

Toluene is first oxidized using potassium permanganate to give benzoic acid. A carboxylic acid group is a meta-directing group. The benzoic acid is then nitrated to give m-nitrobenzoicacid.

Conclusion

Synthesis of m-nitrobenzoicacid from toluene using appropriate reagents is shown in Figure 5.

Interpretation Introduction

(e)

Interpretation:

Synthesis of PhCH2CH2CH2Ph from benzoic acid using appropriate reagents is to be stated.

Concept introduction:

Synthesis is the process of conversion of one compound into another using reagents. For the conversion of one compound into another, the multiple numbers of steps undergo using multiple reagents.

Expert Solution
Check Mark

Answer to Problem 20.47AP

Synthesis of PhCH2CH2CH2Ph from benzoic acid using appropriate reagents is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  10

Explanation of Solution

The synthesis of PhCH2CH2CH2Ph from benzoic acid using appropriate reagents is done using multiple steps shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  11

Figure 6

Benzoic acid is converted into benzoyl chloride in the first step which is then reacted with Grignard’s reagent to give an appropriate ketone which on Clemmensen reduction gives the required product PhCH2CH2CH2Ph.

Conclusion

Synthesis of PhCH2CH2CH2Ph from benzoic acid using appropriate reagents is shown in Figure 6.

Interpretation Introduction

(f)

Interpretation:

Synthesis of given γ-lactone from 4-oxopentanoicacid using appropriate reagents is to be stated.

Concept introduction:

Synthesis is the process of conversion of one compound into another using reagents. For the conversion of one compound into another, the multiple numbers of steps undergo using multiple reagents.

Expert Solution
Check Mark

Answer to Problem 20.47AP

Synthesis of given γ-lactone from 4-oxopentanoicacid using appropriate reagents is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  12

Explanation of Solution

The synthesized compound is γ-lactone is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  13

Figure 7

Synthesis of given γ-lactone from 4-oxopentanoicacid using appropriate reagents is done using multiple steps shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  14

Figure 8

The 4-oxopentanoicacid is first of selectively reduced using sodium borohydride to give 4-hydroxypentanoicacid a γ-hydroxyacid. The 4-hydroxypentanoicacid is converted into required γ-lactone in the presence of acid.

Conclusion

Synthesis of given γ-lactone from 4-oxopentanoicacid using appropriate reagents is shown in Figure 8.

Interpretation Introduction

(g)

Interpretation:

Synthesis of given dicarboxylic acid from norbornene using appropriate reagents is to be stated.

Concept introduction:

Synthesis is the process of conversion of one compound into another using reagents. For the conversion of one compound into another, the multiple numbers of steps undergo using multiple reagents.

Expert Solution
Check Mark

Answer to Problem 20.47AP

Synthesis of given dicarboxylic acid from norbornene using appropriate reagents is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  15

Explanation of Solution

The given dicarboxylic acid is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  16

Figure 9

Synthesis of given dicarboxylic acid from norbornene using appropriate reagents is done in a single step shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  17

Figure 10

The conversion of norbornene into the required dicarboxylic acid is done in a single reaction. The ozonolysis of norbornene with oxidative work gives the required product.

Conclusion

Synthesis of given dicarboxylic acid from norbornene using appropriate reagents is shown in Figure 10.

Interpretation Introduction

(h)

Interpretation:

Synthesis of 5-oxohexanoicacid from 5-bromo-2-pentanone using appropriate reagents is to be stated.

Concept introduction:

Synthesis is the process of conversion of one compound into another using reagents. For the conversion of one compound into another, the multiple numbers of steps undergo using multiple reagents.

Expert Solution
Check Mark

Answer to Problem 20.47AP

Synthesis of 5-oxohexanoicacid from 5-bromo-2-pentanone using appropriate reagents is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  18

Explanation of Solution

Synthesis of 5-oxohexanoicacid from 5-bromo-2-pentanone using appropriate reagents is done in multiple steps shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  19

Figure 11

The compound, 5-bromo-2-pentanone is first of all reacted with ethylene glycol in the presence of acid to protect the carbonyl group. The bromide group is then substituted in the second by cyanide ion. The resultant product is then hydrolyzed to give the required product 5-oxohexanoicacid.

Conclusion

Synthesis of 5-oxohexanoicacid from 5-bromo-2-pentanone using appropriate reagents is shown in Figure 11.

Interpretation Introduction

(i)

Interpretation:

Synthesis of cis-cinnamicacid from PhCCH using appropriate reagents is to be stated.

Concept introduction:

Synthesis is the process of conversion of one compound into another using reagents. For the conversion of one compound into another, the multiple numbers of steps undergo using multiple reagents.

Expert Solution
Check Mark

Answer to Problem 20.47AP

Synthesis of cis-cinnamicacid from PhCCH using appropriate reagents is shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  20

Explanation of Solution

Synthesis of cis-cinnamicacid from PhCCH using appropriate reagents is done in multiple steps shown below.

Organic Chemistry, Chapter 20, Problem 20.47AP , additional homework tip  21

Figure 12

The compound, PhCCH is first of all reacted with NaNH2 and CO2 to give 3-phenylpropiolicacid. The role of NaNH2 is to abstract the acidic proton to generate a carbanion which reacts with CO2 to give carboxylic acid. The 3-phenylpropiolicacid is then reacted with Lindlar’s catalyst which reduces the alkene functional group into cis-alkene and thus gives the required product cis-cinnamicacid.

Conclusion

Synthesis of cis-cinnamicacid from PhCCH using appropriate reagents is Figure 12.

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