chem 219 module 6 Test with Questions Solved
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alkyl: 3-4, aromatic: 9 (resonance sharing in aromatic) - ✔✔pKb of alkyl amines vs
aromatic amines
amine - ✔✔ammonia + alkyl halide =
1. ammonia as nucleophile displaces halide ion via Sn2 reaction
2.sodium hydroxide (base) added to deprotonate the alkylammonium cation to produce
the "free base" of the amine - ✔✔2 steps to alkylation of ammonia and amines
alkyl halide added to an ammonia to create an amine - ✔✔alkylation of ammonia and
amines
secondary amine (R2NH) - ✔✔what does a primary amine alkylate to?
tertiary amine (R3N) - ✔✔What does a secondary amine alkylate to?
quaternary ammonium salt - ✔✔what does a tertiary amine alkylate to?
can produce all degrees of amines - ✔✔what is advantage of alkylation of amines ?
Polyalkylation: yield a mix of amine products because no reaction stops cleanly after a
single alkylation - ✔✔what is the disadvantage of alkylation of amines?
, use large concentration of ammonia or amines as the excess helps the halides not react
with the new amines created - ✔✔how to combat possible polyalkylation?
reduced state - ✔✔all bonds to Nitrogen are either Carbons or Hydrogens
Catalytic Hydrogenation - ✔✔reducing an aromatic nitrogen compound to an
aromatic primary amine on a metal catalyst like nickel or platimum with the addition of
high pressured hydrogen gas
surface-catalyzed reaction - ✔✔H2 + nitro compounds are absorbed to the surface of
the metal where reduction takes place. The reduction product desorbs from the surface
of the metal back into the reaction mixture
Lithium Aluminum Hydride (LiAlH4) - ✔✔what molecule can be used to reduce
amides to amines?
1st, 2nd, and 3rd degree amines - ✔✔what type of amines can be produced by
reducing amides?
tin(II) chloride + HCL followed by aqueous sodium hydroxide - ✔✔chemical reducing
agent to use rather than highly flammable pressurized hydrogen?
primary amines - ✔✔what do nitriles reduce to?
1) LiAlH4 (chemical reagent)
2) H2(g)/Ni (catalytic hydrogenation) - ✔✔what two molecules can be used to reduce
a nitrile?
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