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

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter17: Aldehydes And Ketones
Section: Chapter Questions
Problem 17.60P: 17-60 1-Propanol can be prepared by the reduction of an aldehyde, but it cannot be prepared by the...
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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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