(a) Interpretation: Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed. Concept introduction: The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Question

Protecting Groups and Carbonyls 6) The synthesis generates allethrolone that exhibits high insect toxicity but low mammalian toxicity. They are used in pet shampoo, human lice shampoo, and industrial sprays for insects and mosquitos. Propose detailed mechanistic steps to generate the allethrolone label the different types of reagents (Grignard, acid/base protonation, acid/base deprotonation, reduction, oxidation, witting, aldol condensation, Robinson annulation, etc.) III + VI HS HS H+ CH,CH,Li III I II IV CI + P(Ph)3 V ༼ Hint: no strong base added VI S VII IX HO VIII -MgBr HgCl2,HgO HO. isomerization aqeuous solution H,SO, ༽༽༤༽༽ X MeOH Hint: enhances selectivity for reaction at the S X ☑

Answer 1

Question

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Protecting Groups and Carbonyls 6) The synthesis generates allethrolone that exhibits high insect toxicity but low mammalian toxicity. They are used in pet shampoo, human lice shampoo, and industrial sprays for insects and mosquitos. Propose detailed mechanistic steps to generate the allethrolone label the different types of reagents (Grignard, acid/base protonation, acid/base deprotonation, reduction, oxidation, witting, aldol condensation, Robinson annulation, etc.) III + VI HS HS H+ CH,CH,Li III I II IV CI + P(Ph)3 V ༼ Hint: no strong base added VI S VII IX HO VIII -MgBr HgCl2,HgO HO. isomerization aqeuous solution H,SO, ༽༽༤༽༽ X MeOH Hint: enhances selectivity for reaction at the S X ☑

Draw the complete mechanism for the acid-catalyzed hydration of this alkene. esc 田 Explanation Check 1 888 Q A slock Add/Remove step Q F4 F5 F6 A བྲA F7 $ % 5 @ 4 2 3 & 6 87 Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Ce W E R T Y U S D LL G H IK DD 요 F8 F9 F10 F1 * ( 8 9 0 O P J K L Z X C V B N M H He command

Explanation Check F1 H₂O H₂ Pd 1) MCPBA 2) H3O+ 1) Hg(OAc)2, H₂O 2) NaBH4 OH CI OH OH OH hydration halohydrin formation addition halogenation hydrogenation inhalation hydrogenation hydration ☐ halohydrin formation addition halogenation formation chelation hydrogenation halohydrin formation substitution hydration halogenation addition Ohalohydrin formation subtraction halogenation addition hydrogenation hydration F2 80 F3 σ F4 F5 F6 1 ! 2 # 3 $ 4 % 05 Q W & Å © 2025 McGraw Hill LLC. All Rights Reserved. F7 F8 ( 6 7 8 9 LU E R T Y U A F9

Answer 2

Question

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 3

Question

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 4

Question

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 5

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

Answer 6

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Answer 7

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Answer 10

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Answer 11

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Answer 12

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

Answer 13

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

Answer 14

Expert Solution & Answer

Answer 15

Expert Solution & Answer

Answer 16

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 17

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 18

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 19

Trending nowThis is a popular solution!

Answer 20

Trending nowThis is a popular solution!

Answer 21

Trending nowThis is a popular solution!

Answer 22

Trending now

Answer 23

This is a popular solution!

Answer 24

See solution

Check out sample textbook solution

Answer 25

Ch. 24 - Prob. 24.1P Ch. 24 - Prob. 24.2P Ch. 24 - Prob. 24.3P Ch. 24 - Prob. 24.4P Ch. 24 - Prob. 24.5P Ch. 24 - Prob. 24.6P Ch. 24 - Prob. 24.7P Ch. 24 - Prob. 24.8P Ch. 24 - Prob. 24.9P Ch. 24 - Prob. 24.10P

Chapter 24 Solutions