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 ☑

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
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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
☑
Transcribed Image Text: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 ☑
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