Naming for primary amines

Replace -e w/ -amine

When substituents are the same, what do you name secondary and tertiary amines

di-, tri- amine

Aryl amines vs heterocyclic amines

Aryl: aromatic rings w/ N as substituent Hetero: include N as part of ring

T/F: amines have BP lower than hydrocarbons

False

Are primary and secondary amines H bond?

Yes, to eachother and to water

Are tertiary amines H bond acceptors or donors?

Acceptors (lower BP)

Which bond is stronger? OH or NH?

OH - N is more electronegative and not as polarized a bond as OH

Are alkyl amines sp3 or sp2?

Sp3 - LP occupies p orbital

How can you protonate an amine? What is the product

H3O+ (HCl) - R/S isomers

Are alkyl amines good acids? Why?

No - High pka

How can u deprotonate an amine?

Strong base - BuLi

Which have lower pka? arylamines or alkylamines

Aryl - due to increased stability of CB

What do amines often do when reacting w/ acidic p+?

Form ammonium salts

The more EDG on the N atom, the more _____ the amine

Basic

In substitution rxns w/ primary amines, what is the Nu?

The amine

What is the problem w/ substitution rxns w/ amine?

Overalkylation - N is more Nu w/ EDG

Describe reductive amination

Amine reacts w/ aldehyhde and ketone to make iminium intermediate then reduced by Nu-H

What reagent cannot be used in reductive amination?

LAH

Why is NaBH3CN a weaker reducing agent?

EWG pulls e- density from H atom = less Nu