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Dr. Sheppard CHEM 4201 Fall 2014 Exam I Study Guide: Max Max

The document provides a study guide for an exam covering topics in organic chemistry including conjugated systems, pericyclic reactions, molecular orbital theory, UV spectroscopy, polymers, and carbonyl condensation reactions. It lists key concepts to review and questions to consider for each topic area. Specifically, it outlines questions about pericyclic reactions like the Diels-Alder reaction and electrocyclic reactions, molecular orbital diagrams and molecular orbitals, different types of polymers and their properties, and carbonyl condensation reactions such as aldol and Claisen condensations.

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92 views4 pages

Dr. Sheppard CHEM 4201 Fall 2014 Exam I Study Guide: Max Max

The document provides a study guide for an exam covering topics in organic chemistry including conjugated systems, pericyclic reactions, molecular orbital theory, UV spectroscopy, polymers, and carbonyl condensation reactions. It lists key concepts to review and questions to consider for each topic area. Specifically, it outlines questions about pericyclic reactions like the Diels-Alder reaction and electrocyclic reactions, molecular orbital diagrams and molecular orbitals, different types of polymers and their properties, and carbonyl condensation reactions such as aldol and Claisen condensations.

Uploaded by

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

Sheppard
CHEM 4201
Fall 2014
Exam I Study Guide

Some questions to consider, topics to review….

I. Conjugated Systems, Pericyclic Reactions, MO Theory, UV Spectroscopy

● What are conjugated/cumulated/isolated double bonds? Which are more stable?


● Describe the structure of 1,3-butadiene (bond length, shape, etc.).
● Describe the s-cis and s-trans conformations. Which is more stable?
● What is the difference between a 1,2- and 1,4-addition product (in electrophilic addition)?
Under what circumstances are you likely to see each product form?
● Compare kinetic control to thermodynamic control.
● What is a pericyclic reaction?
● Describe electrocyclic reactions (starting materials, products, mechanism, conditions,
stereochemistry, etc.).
● Which electrocyclic reactions will be conrotatory? Disrotatory?
● Describe the Diels-Alder cycloaddition reaction (starting materials, products, mechanism,
conditions, stereochemistry, regiochemistry, etc.).
● What is a diene? Dienophile?
● Which starting material in a Diels-Alder reaction is likely to contain an EDG? EWG?
● What is the endo rule?
● How does the Diels-Alder reaction relate to insecticides? Read the provided Essay.
● Which cycloaddition reactions are favored thermally? Photochemically?
● What is a sigmatropic rearrangement? Given a sigmatropic rearrangement reaction,
classify it as a [#,#] reaction (e.g. [1,5], [3,3], etc.)
● What happens in the Claisen and Cope sigmatropic rearrangements? What are the
mechanisms for these rearrangements?
● What are molecular orbitals?
● What does it mean for a MO to be bonding? Antibonding? Which is lower in energy?
● Describe constructive and destructive overlap.
● Describe the MOs of ethylene and 1,3-butadiene (bonding vs. antibonding, number of
nodes, etc.). be able to identify the HOMO and LUMO in both the ground state and excited
state.
● How do you predict if an electrocyclic reaction is disrotatory or conrotatory? Be able to
answer this question for both thermal and photochemical reactions.
● How do you predict if a cycloaddition reaction is allowed or forbidden? Be able to
answer this question for both thermal and photochemical reactions.
● What do suprafacial and antarafacial mean? How do you know if a reaction is
antarafacial or suprafacial?
● What is the UV region of the EM spectrum?
● How does UV spectroscopy work?
● What is the relationship between max and molecular structure?
● Be able to predict max for a given molecule.

II. Polymers

● What is a polymer? Copolymer? Monomer, dimer, oligomer?


Dr. Sheppard
CHEM 4201
Fall 2014
Exam I Study Guide

● What are the different types of copolymers?


● Describe the structures of natural rubber and synthetic rubber. What is vulcanized rubber?
● Describe the different types of structures and properties of polymers.
● What does it mean if a polymer is biodegradable? How can biodegradability be
controlled?
● What structural features tend to be associated with rigid polymers? Elastic polymers?
● How are polymers recycled? What are some problems with the recycling processes?
● How are polymers classified?
● What are thermoplastics? Thermoset plastics? Plasticizers?
● Describe chain/addition polymerization reactions, including the radical, cationic and
anionic mechanisms. Which monomers are likely to undergo this type of polymerization?
● Describe step-growth/condensation polymerization reactions. Which polymers are likely
to be synthesized by this type of polymerization?
● Be familiar with the structures and give some examples of uses for the following
polymers:
Dr. Sheppard
CHEM 4201
Fall 2014
Exam I Study Guide

o Polyethylene (HDPE and LDPE) o Cyanoacrylates


o Polystyrene (PS) o Nylons
o Polyvinyl chloride (PVC) o Kevlar
o Polytetrafluoroethylene (PTFE) o Poly(ethylene
o 1,1-Dichloroethylene terephthalate) (PETE)
o Polypropylene (PP) o Spandex
o Polymethyl methacrylate o Polyurethanes
(PMMA) o Polycarbonates
o Polyethyl acrylate (PEA) o Poly(dimethylsiloxane)
o Poly(2-hydroxyethyl o Polyglycolide (PGA)
methacrylate) o Polylactide (PLA)
Dr. Sheppard
CHEM 4201
Fall 2014
Exam I Study Guide

● How are acryalates named?


● How are polymers chosen/designed for a particular application? What properties are
important?

III. Carbonyl Condensation Reactions

● What is the aldol condensation reaction? Be able to draw the products from a reaction (given
starting materials) and be able to draw the starting materials (given products).
● What is a -hydroxy carbonyl? -unsaturated carbonyl? -diketone? -ketoester?
● What is an enolate? What is the best base to use to create an enolate from a neutral carbonyl?
● How does the enolate react with an electrophile? Be able to draw a mechanism.
● What is the haloform reaction?
● What does the product look like if the aldol product is dehydrated? What is the catalyst used
in the dehydration step?
● What is a mixed or crossed aldol condensation reaction? How many products can be formed?
Why are benzaldehyde and formaldehyde good choices as starting materials for this type of
aldol reaction?
● What happens if the aldol reaction is intramolecular? What types of ring structures are
formed?
● What is the Claisen condensation reaction? How is it different from the aldol condensation
reaction?
● If both a ketone and an ester are used in a Claisen reaction, which one is more likely to act as
the enolate?

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