Amines and Nitrogen-Containing Compounds Flashcards
What’s a carbamate?
RNHC(O)OR’
What’s isocyanate?
RN=C=O
How to form a carbamate?
Attack an isocyanate with an alcohol
What’s an enamine?
Equivalent of enol but with amine instead of hydroxyl
Imine
N=C
Nitrile
N(triple bond)C
When diazo compounds lose N2, what do they become?
Highly reactive carbenes, carbons with 6 valence e-s
When azide compounds lose N2, what do they become?
Nitrenes, nitrogen analog of carbene.
Explain nitrogen inversion
Tertiary nitrogen compounds are chrial, but enantiomers interconvert rapidly as the lone pairs flip from one side to the other.
What’s the foundation mechanism for creation of alkylamine?
An SN2 reaction with an alkyl halide
How to avoid side products in formation of alkylamine?
Protect the nitrogen so it cannot react again. Gabriel synthesis makes nitrogen tertiary (starting with pthalimide) then releases it with hydrolysis.
4 ways to form amines from reduction rxns?
- Reduction of a nitro compound (esp aromatic) with Zn + HCl
- Reduction of nitrile with LAH
- Reductive amination. Add amine to carbonyl forming imine. Then reduce to form amine.
- Reduction of an amide with LAH
How to turn amine into alkene?
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.
