-
You can provide a proper, unique name
for an amine, given its structure.
- You can draw a correct structure for an amine, given
its name. You recognize the difference between primary, secondary and tertiary amines and
quaternary ammonium salts.
- You understand the hydrogen bonding ability of
primary and secondary amines.
- You recognize the function of the amine group as a base and as a weak acid. You
understand the impact of conjugation on the
basicity of nitrogen.
- You know the IR stretches
for amines, and you know how amine groups affect proton and 13C
chemical shifts in the NMR spectrum.
- You understand the important fragmentation of amine parent ions in the mass spectrometer by α-cleavage.
- You know how an amine may be prepared by alkylation
of ammonia or other amines, and the selectivity problems engendered by this approach.
- You know how to use phthalimide as a protected form
of ammonia for the synthesis of primary amines in the Gabriel synthesis.
- You recall how amines react with aldehydes and ketones.
- You know how to use reductive amination as a general
method for preparing amines.
- You know how to convert a carboxylic acid amide to an amine using LiAlH4.
- You recognize that formation of a quaternary
ammonium ion creates a good leaving group. This allows the molecule to undergo
Hofmann elimination to form an alkene. You know the preferred regiochemistry of
Hofmann elimination. (Compare to Section 11.6)
- You know which compounds cause nitrosation of
amines.
- You understand how, under acidic conditions, nitrosoamines convert to diazonium salts, and that this serves as a strategy for turning an NH2 into a leaving group.
- For fun: take a look at the class of
amine-containing natural products called the alkaloids.
Note: The Mannich Reaction (Section 21-9) will not be covered until we get into Chapters 18 and 23.
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