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Organic Chemistry

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Aldehydes and Ketones

Question
14 out of 16
 

Students of an organic chemistry class conducted several experiments with aldehydes and ketones. Some of the reactions are summarized below:

Experiment 1

Acetophenone was reacted with Reagent A. The product was ethyl benzene.

image\Ch 22 pass, g1.png

Experiment 2

Propanal underwent acid-catalyzed reaction with alcohol.


image\Ch 22 pass, g2.png

Experiment 3

image\Ch 22 pass, g3.png

Experiment 3 involved merely the analysis of a conversion. Students were asked to discuss a method to accomplish this synthesis reaction.

Experiment 4

image\Ch 22 pass, g4.png


In Experiment 3, which of the following is a possible scenario?

A Reaction is possible, because propanal can be directly oxidized to form the product indicated
B Reaction is not possible, because you cannot convert an aldehyde to a secondary alcohol
C Reaction is possible, if the reactant is treated with an appropriate Grignard reagent followed by hydrolysis
D Reaction is not possible, because aldehyde carbonyls are nucleophilic and are thus unreactive
Ans. C In the experiment, 3-propanal is converted to 2-butanol. Direct oxidation is not an option because there aren't enough carbons in propanal to form an alcohol with four carbons. So Choice A is ruled out. Choice B is not completely true. With appropriate steps, the reaction is possible. One of the best ways to accomplish the reaction is to first treat the reactant with the appropriate Grignard reagent. Since Grignard reagents are nucleophilic, they can add to the carbonyl group. This extends the carbon chain. The product formed can be then hydrolyzed to form the alcohol.

image\Solutions ch 22, Q 14.png

Aldehydes and Ketones Flashcard List

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