Reactions of Aldehydes and Ketones with Amines-Practice Problems

In the previous two posts, we have seen that aldehydes and ketones react with primary amines, in mildly acidic conditions, forming an imine (a Schiff base). The reaction with secondary amines produces enamines:

 

 

Below are a few practice exmmples of these reactions :

Practice

1.

Draw the mechanism for the reaction of the following ketones with a primary and a secondary amine to demonstrate the formation of the imine and enamine:

Answer

Check the following posts for a detailed mechanism of these reactions:

2.

Predict the product for each reaction of aldehydes and ketones with amines:

a)
Answer

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b)
Answer

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c)
Answer

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d)
Answer

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e)
Answer

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Solution

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3.

Draw a mechanism for the formation of products B and D:

 

 

a)
Answer

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b)
Answer

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4.

Propose a mechanism for the following condensation of cyclopentadienyl with carbonyl compounds:

 

Answer

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5.

Predict the major product(s) obtained when each of the following compounds undergoes hydrolysis in the presence of an acid:

a)
Answer

b)
Answer

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c)
Answer

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d)
Answer

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e)
Answer

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f)
Answer

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g)
Answer

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h)
Answer

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Solution

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