medchem 20 Flashcards
amines have lone pairs which makes them —
basic and nucleophiles
– have higher boiling point that alkanes due to the —- bonding
- amines
- intermolecular hydrogen bonding
amines react as base if there’s a — and produce –
- acid proton
- amine salt
arrange the basicity of the following
annaline
ammonia
cyclohexylamine
ch3nh2
ch3nh2 > cyclohexylamine > ammonia > aniline ( bc the lone pairs are not available in the aliphatic amines and they are in an aromatic sexts )
electron — increases the basicity if amines as they push the electrons density towards the nitrogen and making it easier to accept a proton so its a better base
donating groups
electron — groups decreases the basicity of the amines and pull the electrons density away from the N making it less easy to accept a proton and is a poor base
withdrawing groups
reactions of amines w/ alkyl halids:
ammonia + ch3ch2-br –>
1 amine –>
2nd amine –>
3rd amine —>
primary amine (hydrobromide salt )
secondary amine (hydrobromide salt
teritary amine (hydrobromide salt )
quantatry amine ( ammonium bromide salt )
reactions of amines w/ carbonyl groups produce
immine (schiff base + h20 )
reduction of imime ( by h2 and metal catalyst ) leads to –
amine
amines can be produced directly from —– by the formation of — and their — in a — step
- aldehyde , keton
- imine
- reduction ( reduction of mines by hydrogenation aka h2 or Ni aka a metal or by reducing agent )
- single
amines cant be formed by —- under normal conditions bc they will produce —
- carbolyxic acid
- amine salts ( c.a + amines as a base —> amine salts )
many amine drugs as —- which is a local anasethic and are — and are poorly soluble in —- which is why they are administered as —— to make them —-
- lidocaine
- lipophilic
- blood plasma
- hydrochloride salts
- water soluble
( only one will be protonated )
so they are formulated as hydrochloride and not dihydrochloide due to the solubility and stability of hydrochlorides