Amino Products - Organic Chemistry

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Question

A secondary alkyl halide is treated with , then , then acid. The final product is __________.

Answer

The group replaces the halogen as the halogen is a better leaving group. Lithium aluminum hydride is a strong reducing agent. It takes nitrogen-nitrogen bonds and allows for nitrogen hydrogen bonds to be formed instead. A primary nitrogen is bonded to two hydrogens and one R group. After reduction, a primary amine is formed.

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Question

Screen shot 2015 12 29 at 6.37.18 pm

What product would be obtained for the acid catalyzed reaction shown above?

Answer

The reaction given is for the nucleophilic addition of a secondary amine to a ketone. Below is the mechanism for this acid catalyzed reaction:

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The protonation of the hydroxyl group makes it a better leaving group.

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