Organic Chemistry : Help with Amine Synthesis

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #1 : Help With Amine Synthesis

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

Possible Answers:

None of the other answers

a primary amine

a secondary amine

phthalimide

an amide

Correct answer:

a primary amine

Explanation:

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.

Example Question #2 : Help With Amine Synthesis

Screen shot 2015 12 29 at 6.37.18 pm

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

Possible Answers:

Screen shot 2015 12 29 at 6.43.04 pm

Screen shot 2015 12 29 at 6.45.53 pm

Screen shot 2015 12 29 at 6.42.00 pm

Screen shot 2015 12 29 at 6.42.32 pm

Correct answer:

Screen shot 2015 12 29 at 6.42.00 pm

Explanation:

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

Screen shot 2015 12 31 at 11.33.07 am

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

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