Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 20, Problem 20.43P
Interpretation Introduction

(a)

Interpretation: The product formed when the α,β unsaturated ketone A is treated with the NaBH4, CH3OH is to be predicted.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Expert Solution
Check Mark

Answer to Problem 20.43P

The product formed when the α,β unsaturated ketone A is treated with the NaBH4, CH3OH is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  1

Figure 1

Explanation of Solution

The reaction that shows the formation of product when α,β unsaturated ketone reacts with NaBH4, CH3OH is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  2

Figure 2

In the given reaction, sodium borohydride is used as a reducing agent. Sodium borohydride is used for the reduction of carbonyl compounds to alcohols.

Conclusion

The product formed when the α,β unsaturated ketone A is treated with the NaBH4, CH3OH is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  3

Figure 1

Interpretation Introduction

(b)

Interpretation: The product formed when the α,β unsaturated ketone A is treated with the H2(1equiv), PdC is to be predicted.

Concept introduction: Addition of hydrogen takes place across a double bond of alkenes to form alkanes. This process is known as hydrogenation. It takes place in the presence of catalysts such as nickel, platinum or palladium.

Expert Solution
Check Mark

Answer to Problem 20.43P

The product formed when the α,β unsaturated ketone A is treated with the H2(1equiv), PdC is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  4

Figure 3

Explanation of Solution

The reaction that shows the formation of product when α,β unsaturated ketone reacts with H2(1equiv), PdC is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  5

Figure 4

In the given reaction, hydrogenation of alkene takes place in the presence of palladium.

Conclusion

The product formed when the α,β unsaturated ketone A is treated with the H2(1equiv), PdC is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  6

Figure 3

Interpretation Introduction

(c)

Interpretation: The product formed when the α,β unsaturated ketone A is treated with the H2(excess), PdC is to be predicted.

Concept introduction: Addition of hydrogen takes place across a double bond of alkenes to form alkanes. This process is known as hydrogenation. It takes place in the presence of catalysts such as nickel, platinum or palladium.

Expert Solution
Check Mark

Answer to Problem 20.43P

The product formed when the α,β unsaturated ketone A is treated with the H2(excess), PdC is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  7

Figure 5

Explanation of Solution

The reaction that shows the formation of product when α,β unsaturated ketone reacts with H2(excess), PdC is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  8

Figure 6

In the given reaction, excess hydrogen is used which will reduce both keto group and double bond. This results in the formation of a saturated compound.

Conclusion

The product formed when the α,β unsaturated ketone A is treated with the H2(excess), PdC is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  9

Figure 5

Interpretation Introduction

(d)

Interpretation: The product formed when the α,β unsaturated ketone A is treated with the [1]CH3Li;[2]H2O is to be predicted.

Concept introduction: Methyllithium in the presence of water reduces carbonyl compounds into alcohol. Methyllithium is a reducing agent.

Expert Solution
Check Mark

Answer to Problem 20.43P

The product formed when the α,β unsaturated ketone A is treated with the [1]CH3Li, [2]H2O is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  10

Figure 7

Explanation of Solution

The reaction that shows the formation of product when α,β unsaturated ketone reacts with [1]CH3Li, [2]H2O is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  11

Figure 8

The product formed in the given reaction is 1,2 addition product. The reagent used in this reaction is organolithium reagent. This reagent attacks on the carbonyl compound to form alkoxides. In the next step, protonation with water takes place to give the final product.

Conclusion

The product formed when the α,β unsaturated ketone A is treated with the [1]CH3Li, [2]H2O is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  12

Figure 7

Interpretation Introduction

(e)

Interpretation: The product formed when the α,β unsaturated ketone A is treated with the [1]CH3CH2MgBr, [2]H2O is to be predicted.

Concept introduction: Grignard reagent is prepared by the reaction of alkyl or aryl bromide with magnesium metal in the presence of ether. The reaction of Grignard reagent with an aldehyde/ketone followed by hydrolysis yields an alcohol.

Expert Solution
Check Mark

Answer to Problem 20.43P

The product formed when the α,β unsaturated ketone A is treated with the [1]CH3CH2MgBr, [2]H2O is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  13

Figure 9

Explanation of Solution

The reaction that shows the formation of product when α,β unsaturated ketone reacts with [1]CH3CH2MgBr, [2]H2O is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  14

Figure 10

In the given reaction, Grignard reagent is used. This reagent attacks on the carbonyl compound to form alkoxides. In the next step, protonation with water takes place to give the final product.

Conclusion

The product formed when the α,β unsaturated ketone A is treated with the [1]CH3CH2MgBr, [2]H2O is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  15

Figure 9

Interpretation Introduction

(f)

Interpretation: The product formed when the α,β unsaturated ketone A is treated with the [1](CH2=CH)2CuLi, [2]H2O is to be predicted.

Concept introduction: The steps involved in the reaction of ketone with organolithium reagent are as follows:

• The first step involves the reduction of carbonyl group into single bonds.

• The second step is the addition of R group from organometallic reagent and hydrogen to oxygen.

Expert Solution
Check Mark

Answer to Problem 20.43P

The product formed when the α,β unsaturated ketone A is treated with the [1](CH2=CH)2CuLi, [2]H2O is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  16

Figure 11

Explanation of Solution

The reaction that shows the formation of product when α,β unsaturated ketone reacts with [1](CH2=CH)2CuLi, [2]H2O is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  17

Figure 12

In the given reaction, organo copper reagent reacts with unsaturated carbonyl compound and forms carbon–carbon double bond with the beta carbon as shown in the above reaction.

Conclusion

The product formed when the α,β unsaturated ketone A is treated with the [1](CH2=CH)2CuLi, [2]H2O is shown below.

Organic Chemistry-Package(Custom), Chapter 20, Problem 20.43P , additional homework tip  18

Figure 11

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Chapter 20 Solutions

Organic Chemistry-Package(Custom)

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