In each reaction box, place the best reagent and conditions from the list below. (A reagent may be used more than once…
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Question “In each reaction box, place the best reagent and conditions from the list below. (A reagent may be used more than once…”
In each reaction box, place the best reagent
and conditions from the list below. (A reagent may be used more
than once.) Hint: step 1 is conducted at �78 �C.
Answer
This question can be solved using the concept of formation of a ketone by a series of reactions between organolithium compounds and ester to create an alcohol, and then the oxidation.
Organolithium reagent acts in a nucleophile and attacks carbonyl carbon to create an intermediate metal alkoxide sodium. Acidic work up transforms the metal alkoxide sodium into an alcohol, which is then oxidized by an oxidizing agent to make the carbonyl compound.
DIBAL H at - 70^\circ {\rm{C}}
Organolithium reagent reacts with aldehydes to produce primary or secondary alcohols. The alcohol is made up of equal number carbon atoms from the carbonyl compound as well as the organolithium-reagent.
The formula for an organolithium reagent is $math_tag_1
Hydrolysis of aldehydes reacting with an organolithium reagent, followed by reaction to form an alcohol (new {\rm{C}} - {\rm{O}}).
Jones reagent \left( {{\rm{Cr}}{{\rm{O}}_3},{{\rm{H}}_2}{\rm{S}}{{\rm{O}}_4}} \right)
This is the reaction to reduce methyl acetate into acetaldehyde:
This is the reaction of the nucleophilic attack on phenyllithium by acetaldehyde in order to make the alcohol:
Acetophenone is produced by oxidation of alcohol.
This is the reaction:
Ans:
The complete reaction to convert the reactant to the product is as follows:
Conclusion
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