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C341 Final Exam Study Guide
Summer 2016
General information: 8:00 AM- 11:00AM on Friday, July 29 in CH122
Format: 200 points, cumulative, similar format to other exams
Approximate point distributions:
~1/3 mechanism
Draw the arrow mechanism (substitution, elimination, addition,
rearrangements, redox)
Answer questions based on mechanisms
~1/3 reagents, reactions
Predict the major product with stereochemistry and regiochemistry
Provide the correct reagents
Multistep synthesis
~1/3 miscellaneous concepts from list below
Tips for studying:
 Work from the end of the course to the beginning (study backwards). Emphasize
chapters 8-11 and 17-18. Chapters 1-7 were the foundation for these chapters.
Although there will be some questions directly from chapters 1-7, most of those
concepts will be covered in questions from chapter 8-11 and 17-18.
 Print blank discussion problem sets and write full answer before checking key
 Retake old exams and quizzes, then check your answers
 Do practice chapter problems listed under Daily Homework to see which concpets
you need the most review.
A list of major topics (not all inclusive)
Formal charge, resonance structures, hybridization, bond-line structures, acid/base
equilibria, pKa’s, trends in acidity/basicity, functional groups, alkane nomenclature,
conformational analysis, Newman projections, causes of strain, cyclohexane ring
structures, chiral, achiral, R/S nomenclature, enantiomers, diastereomers, optically active,
meso compounds, arrow mechanisms, transition states, rate limiting steps, activation
energy, Hammond postulate, exothermic/endothermic reactions, E/Z nomenclature,
addition reactions, Markovnicov’s rule, anti-Marcovnicov product, regiochemistry of
additions, stereochemistry of additions, reactions of alkynes, acidity of terminal alkynes,
calculating change in bond dissociation energy for reaction, nucleophile, leaving group,
substitution reactions, SN1 mechanism, SN2 mechanism, alkene classifications, alkene
stability, elimination reactions, Zaitsev’s rule, E1 mechanism, E2 mechanism, E1cb
mechanism, anti-periplanar, comparing substitution and elimination mechanisms,
synthesis of ethers, alcohols, and epoxides, dehydration of alcohols, carbocation
rearrangements, reactions of alcohols/ethers/epoxides, multistep synthesis, protecting
groups, redox reactions, reagents for redox reactions, Grignard reaction
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1. Mechanisms. These are the very basic types of mechanisms. You should also be able to
explain regiochemistry and stereochemistry outcomes, as well as rearrangements, etc. You
should be able to apply these basic mechanisms to more challenging molecules, or to
explain why an expected result does not happen.
2. Structure (formal charge, hybridization, aromatic, resonance, stereochemistry, conformational
analysis)
A. Answer the following questions pertaining to this structure.
O
H
N
A. How many hydrogens? How many lone pairs?
B. Label the structure with any missing formal charges.
C. Draw at least two more resonance structures and rank them from most major
contributor to most minor contributor.
D. Mark all the chiral centers and label any designated chiral centers R or S.
B. Would you expect the elimination of cis-1-t-butyl-4-chlorocyclohexane using a strong base to be
faster or slower than the elimination of chlorocyclohexane with a strong base?
3. Acid/base reactions
For each of the following compounds, circle the most acidic hydrogen. Give an approximate pKa
value. Would this compound be deprotonated by HO-? Would this compound be deprotonated by
H2N-? Draw the conjugate base of each acid.
A.
B.
O
C.
O
OH
O
4. Predict the MAJOR products. Include stereochemistry where needed. Indicate the type of
mechanism (electrophilic addition, E1, E2, E1cb, Sn1, Sn2, radical.)
5. Multistep synthesis. Provide all necessary reagents, and explain why a protecting group
is necessary.