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Chem 282

The document outlines learning outcomes and questions to help students prepare for their midterm exam in CHEM 282. It covers topics like conjugated unsaturated systems, alkadienes and polyunsaturated hydrocarbons, aromatic compounds, reactions of aromatic compounds, side chain reactions, alkenylbenzenes, alcohols and ethers, epoxides, and making alcohols from carbonyl compounds. Students are asked to define key terms, draw out reaction mechanisms, and explain concepts like stability, reactivity, and synthesis strategies.

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154 views3 pages

Chem 282

The document outlines learning outcomes and questions to help students prepare for their midterm exam in CHEM 282. It covers topics like conjugated unsaturated systems, alkadienes and polyunsaturated hydrocarbons, aromatic compounds, reactions of aromatic compounds, side chain reactions, alkenylbenzenes, alcohols and ethers, epoxides, and making alcohols from carbonyl compounds. Students are asked to define key terms, draw out reaction mechanisms, and explain concepts like stability, reactivity, and synthesis strategies.

Uploaded by

Urla
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd

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

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