CHEM 219 MODULE 6 COMPREHENSIVE
EXAM PAPER WITH FULL QUESTIONS AND
RELIABLE ANSWERS
◉ NaBH4 (Sodium borohydride)
or catalytic hydrogenation
Answer: reducing agents for reductive aminiation?
◉ avoids polyalkylation
Answer: why is reductive amination superior to direct alkylation?
◉ Nucleophilic Acyl Substitution
Answer: amines function as nitrogen nucleophiles and the amine
is acylated to create an amide
◉ 1st and 2nd degree amines
Answer: which amines can undergo nucleophilic acyl
substitution?
◉ tertiary amines do not have NH bonds to substitute an R-C=O
bond for a hydrogen
Answer: why cant 3rd degree amines undergo nucleophilic acyl
substitution?
, ◉ pyridine or non-nucleophilic bases
Answer: what is used to neutralize the acid byproduct of
nucleophilic acyl substitution?
◉ diazotization of primary aromatic amines
Answer: what unique reaction does aniline undergo with nitrous
acid (HONO)?
◉ very low temperatures
Answer: what temps most diazotization be reacted at?
◉ generated by combining sodium nitrate (NaNO2) with
concentrated HCL at very low temps
Answer: how is the nitrous acid generated for diazotization?
◉ Diazonium Ion
Answer: N(triple bond)N+
(no NH bonds)
◉ only primary amines (have the 2 hydrogen bonds necessary for
reaction to occur)
Answer: which amines can undergo diazotization?
◉ leave a nitrogen gas (bubbles out of the mixture)
EXAM PAPER WITH FULL QUESTIONS AND
RELIABLE ANSWERS
◉ NaBH4 (Sodium borohydride)
or catalytic hydrogenation
Answer: reducing agents for reductive aminiation?
◉ avoids polyalkylation
Answer: why is reductive amination superior to direct alkylation?
◉ Nucleophilic Acyl Substitution
Answer: amines function as nitrogen nucleophiles and the amine
is acylated to create an amide
◉ 1st and 2nd degree amines
Answer: which amines can undergo nucleophilic acyl
substitution?
◉ tertiary amines do not have NH bonds to substitute an R-C=O
bond for a hydrogen
Answer: why cant 3rd degree amines undergo nucleophilic acyl
substitution?
, ◉ pyridine or non-nucleophilic bases
Answer: what is used to neutralize the acid byproduct of
nucleophilic acyl substitution?
◉ diazotization of primary aromatic amines
Answer: what unique reaction does aniline undergo with nitrous
acid (HONO)?
◉ very low temperatures
Answer: what temps most diazotization be reacted at?
◉ generated by combining sodium nitrate (NaNO2) with
concentrated HCL at very low temps
Answer: how is the nitrous acid generated for diazotization?
◉ Diazonium Ion
Answer: N(triple bond)N+
(no NH bonds)
◉ only primary amines (have the 2 hydrogen bonds necessary for
reaction to occur)
Answer: which amines can undergo diazotization?
◉ leave a nitrogen gas (bubbles out of the mixture)
