Propose a multi-step synthetic route to form the polycyclic molecule on the right hand side using the following reagents on the left hand side of the arrows: i) cyclic ketone; ii) a,ẞ-unsaturated ketone; iii) either the organocuprate OR the organolithium reagent listed; and ii) any other reagents or solvents of your choosing The depicted reagents represent all necessary building blocks that are directly incorporated into the molecule on the right, however you should use additional reagents to help facilitate its construction based on Chem 110 content from Chapters 21 and 23. This is a multi-step synthesis and not all reagents will be used at the same time. When describing your solution, show the stable intermediates along your proposed synthetic route and number the individual synthetic steps. You do not have to worry about stereochemistry in this particular question. For two (2) of your proposed steps, show individual mechanistic arrows that show the flow of electrons during that specific chemical transformation. Mechanisms for every individual reaction are not needed. g) (0), -CuLi or 2 ? HO

Organic Chemistry
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Chapter17: Alcohols And Phenols
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Problem 71AP: A problem often encountered in the oxidation of primary alcohols to acids is that esters are...
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Propose a multi-step synthetic route to form the polycyclic molecule on the right
hand side using the following reagents on the left hand side of the arrows:
i) cyclic ketone;
ii) a,ẞ-unsaturated ketone;
iii) either the organocuprate OR the organolithium reagent listed; and
ii) any other reagents or solvents of your choosing
The depicted reagents represent all necessary building blocks that are directly
incorporated into the molecule on the right, however you should use additional reagents
to help facilitate its construction based on Chem 110 content from Chapters 21 and 23.
This is a multi-step synthesis and not all reagents will be used at the same time. When
describing your solution, show the stable intermediates along your proposed
synthetic route and number the individual synthetic steps. You do not have to worry
about stereochemistry in this particular question.
For two (2) of your proposed steps, show individual mechanistic arrows that show
the flow of electrons during that specific chemical transformation. Mechanisms for every
individual reaction are not needed.
g)
(0),
-CuLi or
2
?
HO
Transcribed Image Text:Propose a multi-step synthetic route to form the polycyclic molecule on the right hand side using the following reagents on the left hand side of the arrows: i) cyclic ketone; ii) a,ẞ-unsaturated ketone; iii) either the organocuprate OR the organolithium reagent listed; and ii) any other reagents or solvents of your choosing The depicted reagents represent all necessary building blocks that are directly incorporated into the molecule on the right, however you should use additional reagents to help facilitate its construction based on Chem 110 content from Chapters 21 and 23. This is a multi-step synthesis and not all reagents will be used at the same time. When describing your solution, show the stable intermediates along your proposed synthetic route and number the individual synthetic steps. You do not have to worry about stereochemistry in this particular question. For two (2) of your proposed steps, show individual mechanistic arrows that show the flow of electrons during that specific chemical transformation. Mechanisms for every individual reaction are not needed. g) (0), -CuLi or 2 ? HO
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