Book Cover Organic Chemistry 4e Carey
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Chapter 22: Amines



Overview | Alkylation of Amines by Alkyl Halides | Reaction of Amines with Aldehydes and Ketones | Preparation of Amides | Hofmann Elimination | Electrophilic Aromatic Substitution of Aryl Amines | Nitrosation of Amines |


Reactions of Primary Amines with Aldehydes and Ketones

Chapter 22: Amines

(review of Chapter 17)

Reaction type:  Nucleophilic Addition then Elimination

Summary

NUCLEOPHILIC ADDITION OF A PRIMARY AMINE GIVING AN IMINE.
Step 1:
An acid/base reaction. Protonation of the carbonyl activates it and makes it more susceptible to attack by a neutral nucleophilic like the N of a primary amine.
formation of an imine
Step 2:
Attack of the N nucleophile at the electrophilic C of the C=O group with the electrons from the p bond going to the +ve O.
Step 3:
An acid/base reaction. Removal of the proton neutralizes the +ve charge on the N and forms the carbinolamine intermediate.
Step 4:
To form the imine we need to dehydrate. However, before -OH leaves it needs to be protonated, so a simple acid/base reaction.
Step 5:
Use the electrons of the N to help push out the leaving group, a neutral water molecule, this leaves us with an iminium ion.
Step 6:
An acid/base reaction. Deprotonation of the iminium N reveals the imine product and regenerates the acid catalyst.

 

Reactions of Secondary Amine Derivatives with Aldehydes and Ketones
(review of Chapter 17)

preparation of enamines
                                                                          enamine

Reaction type:  Nucleophilic Addition then Elimination

Summary

NUCLEOPHILIC ADDITION OF A SECONDARY AMINE GIVING AN ENAMINE.
Step 1:
An acid/base reaction. Protonation of the carbonyl activates it and makes it more susceptible to attack by a neutral nucleophilic like the N of a secondary amine.
formation of an enamine
Step 2:
Attack of the N nucleophile at the electrophilic C of the C=O group with the electrons from the p bond going to the +ve O.
Step 3:
An acid/base reaction. Removal of the proton neutralizes the +ve charge on the N and forms the carbinolamine intermediate.
Step 4:
To form the enamine we need to dehydrate. However, before -OH leaves it needs to be protonated, so a simple acid/base reaction.
Step 5:
Removal of a proton from an adjacent C allows the p bond to form and loss of the leaving group, a neutral water molecule, creating the enamine.


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