Predict the products and propose mechanisms for the reactions of ketones and aldehydes with oxidizing and reducing agents, amines, alcohols, and phosphorus ylides.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
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Problem 36MP: It is not uncommon for organic chemists to prepare acetals by an exchange-type process known as...
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Predict the products and propose mechanisms for the reactions of ketones and aldehydes with oxidizing and reducing agents, amines, alcohols, and phosphorus ylides.

Expert Solution
Step 1

The general structure of aldehyde is shown below:

Chemistry homework question answer, step 1, image 1

The general structure of ketone is given below.

Chemistry homework question answer, step 1, image 2

Step 2

Reaction of Aldehydes:

Aldehyde + reducing agent (LiAlH4) ----> Primary Alcohol

Aldehyde + Oxidizing agent ----> Carboxylic Acid

Aldehyde + Amine ----> Imine

Aldehyde + Alcohol ----> Hemiacetal

Aldehyde + phosphorous ylide ----> Alkene

 

Reaction of Ketones:

Ketone + reducing agent (LiAlH4) ----> Secondary Alcohol

Ketone+ Oxidizing agent ----> No reaction

Ketone + Amine ----> Imine

Ketone + Alcohol ----> Hemiketal

Ketone + phosphorous ylide ----> Alkene

Step 3

1. Reaction of an aldehyde and ketone with reducing agent (LiAlH4) is shown below.

Chemistry homework question answer, step 3, image 1

Chemistry homework question answer, step 3, image 2

Step 4

2. Reaction of Aldehyde and ketone with oxidizing agent is shown below.

Chemistry homework question answer, step 4, image 1

Chemistry homework question answer, step 4, image 2

 

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