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CHE 312 Exam III Review Sheet
Chapter 16
Explain why an aromatic molecule like benzene reacts differently than the
corresponding alkene (actually a –triene)?
What are the two main requirements for a molecule to be classified as aromatic?
Explain how a Frost circle (aka Polygon Rule) allows one to determine whether a
molecule is aromatic or not?
Be able to identify aromatic versus nonaromatic species (using Polygon &
Huckel’s Rules) including recognizing lone pairs on nitrogen atoms as being
basic or not basic. Very useful skill going into biochemistry.
Be able to name benzene compounds including all derivatives & also how to use
prefixes ortho-, meta-, and para-.
Chapter 17
1. Know the basic reactions, reagents, reaction conditions and mechanisms for
electrophilic aromatic substitutions (e.g., halogenations, nitration, etc.).
2. Know the reactions, conditions, reagents and mechanisms for nucleophilic
aromatic substitiution.
3. Know the reactions, conditions and mechanisms involving the benzyne
4. Know the odd reactions for aniline, phenol, anisole, etc. and those of the sidechains including the main reaction reactions.
5. Know the reaction and mechanism for phenol with carbon dioxide in the presence
of hydroxide ion.
6. Be able to explain how an ortho-, para- director works and how to identify it
without memorization. Be able to do the same with a meta- director.
7. Be able to do synthesis and complete the reactions involving o,p- and mdirectors.
8. Know the times that the Friedel-Crafts reactions do not occur.
9. Know when the NH2 group is converted to a meta director and how to avoid this
problem with the reversible reaction with acetyl chloride. Be able to employ this
set of reactions in synthesis problems as well.
Chapter 18
Nomenclature of aldehydes and ketones
Reactions to produce aldehydes and ketones
Reactions of aldehydes & ketones
Acidic Addition of water across C=O
Basic addition of water across C=O
Wittig reaction – addition of the phosphorus ylide across C=O
Addition of RNH2 across C=O to give C=NR
For acetal formation from C=O
For the reaction of RC(=O)Cl with HAl(OtBu)3 to give the aldehyde
For the reaction of RC(=O)OR’ with (iBu)2AlH to give the aldehyde
For the addition of RLi or RMgX to RCN to give the ketone
Chapter 20
1. Nomenclature of Carboxylic Acids
2. Reactions of Carboxylic Acids
3. Reactions to make Carboxylic Acids
4. General Physical Properties, Trends, IR/NMR Spectroscopy
5. Mechanisms
a) Hydrolysis of nitriles under acidic and basic conditions
b) Fisher esterification – reaction of a a carboxylic acid plus alcohol in
presence of acid
c) Reaction of carboxylic acids with SOCl2
d) Reaction of diazomethane with a carboxylic acid to give a methyl ester
e) Reactions of acid chlorides with carboxylic acids, carboxylate ions,
alcohols, and amines
f) Reactions of anhydrides with alcohols & amines
g) Reactions of esters with amines