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9.2 Preparation of Amines Through SN2 Reactions
A deprotonation is followed by an S 2 reaction.
The product competes with NH for the alkyl halide.
This structure is neither basic nor nucleophilic because it does not have a lone pair.
The synthesis above is a good way to make a quaternary ammonium salt.
It is difficult to stop the reaction at this stage.
The primary amine will react with the alkyl halide.
We will still get a mixture of products even if we only use one mole of alkyl halide and one mole of ammonia.
We will get some polyalkylated products and some ammonia that is not alkyl halide.
We use a clever trick to get around the problem.
Our dummy groups are easy to remove after we alkylate.
The strategy is called Gabriel.
It is a good way to make primary amine from primary alkyl halides.
The negative charge is delocalized by resonance.
The donors that we saw in the end of the previous chapter were similar to this one.
It is stable.
The tertiary alkyl halides cannot be used in this reaction.
Basic conditions are more common than acidic conditions.
The mechanism of hydrolysis is similar to the mechanism of amides.
Many alternative approaches have been developed.
The desired product is generated in this step.
Gabriel synthesis requires the identification of the alkyl halide that is necessary.
Tell me how you would use a Gabriel synthesis to prepare these compounds.
The Gabriel synthesis has some limitations.
It won't work for tertiary alkyl halides.
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