Amines and Nitrogen-Containing Compounds

Question 1

What’s a carbamate?

Answer 1

RNHC(O)OR’

Question 2

What’s isocyanate?

Answer 2

RN=C=O

Question 3

How to form a carbamate?

Answer 3

Attack an isocyanate with an alcohol

Question 4

What’s an enamine?

Answer 4

Equivalent of enol but with amine instead of hydroxyl

Question 5

Imine

Answer 5

N=C

Question 6

Nitrile

Answer 6

N(triple bond)C

Question 7

When diazo compounds lose N2, what do they become?

Answer 7

Highly reactive carbenes, carbons with 6 valence e-s

Question 8

When azide compounds lose N2, what do they become?

Answer 8

Nitrenes, nitrogen analog of carbene.

Question 9

Explain nitrogen inversion

Answer 9

Tertiary nitrogen compounds are chrial, but enantiomers interconvert rapidly as the lone pairs flip from one side to the other.

Question 10

What’s the foundation mechanism for creation of alkylamine?

Answer 10

An SN2 reaction with an alkyl halide

Question 11

How to avoid side products in formation of alkylamine?

Answer 11

Protect the nitrogen so it cannot react again. Gabriel synthesis makes nitrogen tertiary (starting with pthalimide) then releases it with hydrolysis.

Question 12

4 ways to form amines from reduction rxns?

Answer 12

1. Reduction of a nitro compound (esp aromatic) with Zn + HCl
2. Reduction of nitrile with LAH
3. Reductive amination. Add amine to carbonyl forming imine. Then reduce to form amine.
4. Reduction of an amide with LAH

Question 13

How to turn amine into alkene?

Answer 13

Exhaustive methylation, “Hofmann elimination”. Amine converted to quaternary ammonium by repeated SN2’s when supplied with excess methyl iodide. Silver oxide then creates hydroxide which does E2 and forms double bond on the <> substituted carbon.