Chem 282

CHEM 282 Learning Outcomes
Answer these questions to help you understand and consolidate the information better!!
LEGEND
Reaction to remember
Compound class to remember
MIDTERM 1
Conjugated Unsaturated System
 What is a conjugated unsaturated system?
 What is an allylic radical and how is it made?
 Describe the steps of homolytic bond cleavage.
 Draw out the reaction of allylic bromination with N-Bromosuccinimide (NBS).
o Hint: do both overall reaction and the propagation steps
 What happens when you add other nucleophiles after NBS?
o Is the product a radical?
 Draw out the 2 contributing resonance forms + the hybrid form for propene
 What is an allyl cation?
o What is its stability compared to a tertiary, secondary, primary, vinyl and
substituted allylic cation?
Alkadienes + Polyunsaturated Hydrocarbons

 What are alkadienes?
o What are the different types?
o Why is the single bond in an alkadiene shorter than the usual one?
 Which is more stable – a normal alkene or a conjugated diene and WHY?
 Draw out the overall reaction of 1,4 addition (electrophilic attack on conjugated dienes)
o How is it different from regular Markovnikov addition?
o Draw out the mechanism
 Describe the Kinetic vs Thermodynamic product
o How do you get each of them?
 Draw out the overall reaction of Diels-Alder reaction
o Draw out the mechanism
o Why is stereochemistry important?
 Endo vs Exo groups
o Describe each
o Which of the 2 does the Diels-Alder reaction proceed in?
 What are intramolecular Diels-Alder reactions?
Aromatic Compounds
 What’s the nomenclature for:
o Monosubstituted benzenes
o Polysubstituted benzenes
 What are the effects of various groups on the activity of the benzene?
o Hint: deactivate or activate
 What reactions does benzene NOT go through?
o What conditions are needed for a radical benzene reaction?
 Why is the Kekule structure wrong?
 What is Huckel’s Rule?
 What is the polygon + circle method?
 What are annulenes?
 How can you apply Huckel’s rule to aromatic ions?
 Differentiate between aromatic, antiaromatic, and nonaromatic
 What are some examples of non-benzenoid aromatics?
 What are heterocyclic aromatics?
Reactions of Aromatic Compounds

 Draw out the general mechanism for Electrophilic aromatic substitution
o Draw out the specific mechanisms/reactions for:
 Halogenation
 Nitration
 Sulfonation
 Friedel-Crafts Alkylation
 Friedel-Crafts Acylation
 What are the limitations of the Friedel-Crafts reactions?
 What is a Clemmenson reduction?
 How do the way substituents are added affect reactivity and orientation?
o Hint: ortho, para or meta
o What is the exception to this rule?
 How to tell the position of a substituent (ortho, para or meta)?
Side Chain Reactions

 How does a benzylic radical form?
 What is the benzylic position and what is the nature of the radical formed here?
o What forms when a leaving groups departs from this carbon in an SN1 reaction
(hint: type of cation)
 Draw out the halogenation of a side chain
Alkenylbenzenes
 What is the stability of an alkenylbenzene?
 How is it formed?
 Draw out the reaction of oxidation of side chain
 What are the steps to consider when carrying out a synthesis of a certain benzene
compound?
 What are protecting and blocking groups?
o Give some examples and what they do
 What is the mechanism for aromatic nitration + diazo coupling?
 How does the orientation of a group in disubstituted benznes affect subsequent
subsitutions?
Alcohols and Ethers

 What is the nomenclature for alcohols and ethers?
 What are the methods of alcohol synthesis from alkenes we learned in CHEM 281?
o Hint: 3 main ones
 What are organometallic reagents and what are their properties?
 What is keto-enol tautomerization?
 How do you make alcohols into alkyl halides (CHEM 281 review)
 What are the 3 ways to make ethers?
o Draw them out
 What are silyl ether protecting groups
 What is the one reaction that ethers can engage in?
Epoxides
 What are epoxides?
 How are they formed?
 What are the 2 reactions can they engage in?
Alcohols from Carbonyl Compounds

 what are some properties (ie. Reactivity) of a carbonyl group
 Draw out the GENERAL mechanism of a Nucleophile + ketone/aldehyde reaction
 Draw out oxidation/reduction reactions
 What are the compounds you can make alcohols from?
o What are the reagents?
 How do you oxidize an alcohol to:
o Aldehyde
o Carboxylic acid
o Ketone

Chem 282

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Chem 282

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CHEM 282 Learning Outcomes

Alkadienes + Polyunsaturated Hydrocarbons

Reactions of Aromatic Compounds

Side Chain Reactions

Alcohols and Ethers

Alcohols from Carbonyl Compounds

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