CHEM 219 MODULE 6 ADVANCED EXAM
PREP MATERIAL WITH TESTED QUESTIONS
AND EXPERT SOLUTIONS
◉ small amines (up to 6 carbons) are soluble
Answer: are amines soluble in water? in alcohol?
◉ solubility decreases as molecular weight increases
Answer: amine aqueous solubility does what?
◉ basic and nucleophilic
Answer: are amines acidic or basic?
◉ pKb (lower score = more basic)
Answer: what measures bases
◉ alkyl: 3-4, aromatic: 9 (resonance sharing in aromatic)
Answer: pKb of alkyl amines vs aromatic amines
◉ amine
Answer: 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
Answer: 2 steps to alkylation of ammonia and amines
◉ alkyl halide added to an ammonia to create an amine
Answer: alkylation of ammonia and amines
◉ secondary amine (R2NH)
Answer: what does a primary amine alkylate to?
◉ tertiary amine (R3N)
Answer: What does a secondary amine alkylate to?
◉ quaternary ammonium salt
Answer: what does a tertiary amine alkylate to?
◉ can produce all degrees of amines
Answer: what is advantage of alkylation of amines ?
◉ Polyalkylation: yield a mix of amine products because no
reaction stops cleanly after a single alkylation
Answer: what is the disadvantage of alkylation of amines?
PREP MATERIAL WITH TESTED QUESTIONS
AND EXPERT SOLUTIONS
◉ small amines (up to 6 carbons) are soluble
Answer: are amines soluble in water? in alcohol?
◉ solubility decreases as molecular weight increases
Answer: amine aqueous solubility does what?
◉ basic and nucleophilic
Answer: are amines acidic or basic?
◉ pKb (lower score = more basic)
Answer: what measures bases
◉ alkyl: 3-4, aromatic: 9 (resonance sharing in aromatic)
Answer: pKb of alkyl amines vs aromatic amines
◉ amine
Answer: 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
Answer: 2 steps to alkylation of ammonia and amines
◉ alkyl halide added to an ammonia to create an amine
Answer: alkylation of ammonia and amines
◉ secondary amine (R2NH)
Answer: what does a primary amine alkylate to?
◉ tertiary amine (R3N)
Answer: What does a secondary amine alkylate to?
◉ quaternary ammonium salt
Answer: what does a tertiary amine alkylate to?
◉ can produce all degrees of amines
Answer: what is advantage of alkylation of amines ?
◉ Polyalkylation: yield a mix of amine products because no
reaction stops cleanly after a single alkylation
Answer: what is the disadvantage of alkylation of amines?
