Study Guide for Exam 3
C341 Fall 2013
Important Information:
 7:15-9:15PM, Tuesday, December 3
 Bring your student ID
 Show up 10-15 minutes early
 You may use models, but you may not bring model instructions
 No calculators! No phones!
 Anything else you bring must be in a sealed bag under your chair
Room Assignments:
Last name
A-B in Psychology 101
C-J
in Rawles 100
K-MO in Jordan A100
MP-SC in Woodburn 120
SD-Z in Radio and TV 251
DSS students: If you have provided the instructor with DSS documentation, please report to Education
Building room 1230 at 5:15PM for your exam. Please confirm via email with the instructor if you will be
using this option for exam 3.
Early exams: No one will be permitted to take an exam outside the regularly scheduled room without
PRIOR INSTRUCTOR PERMISSION. If you attempt to do so, you will not be permitted, and you will
receive a zero for the exam.
Exam Content: Chapters 9, 10, 12. (Concepts from chapters on stereochemistry, substitutions, and
eliminations are all applied, but there won’t be problems directly from those chapters.) All material
covered in class, homework, or discussion sections could be on the exam. Some major topics include:
Nomenclature of alkenes and alkynes, Reactions of alkenes (mechanism, regiochemistry, Markovnicov,
anti-Markcovnicov, carbocation stability, transition states, stereochemistry, anti addition, syn addition,
predict the product, provide reagents), Reactions of alkynes (mechanism, enol formation under acid, enol
formation under basic, regiochemistry, stereochemistry of partial reductions, alkylation of alkynes);
multistep synthesis
Suggestions for studying:
 First, review daily homework and discussion sheets, especially problems you initially missed
 Next, work through additional problems given on last page of syllabus
 Use the practice problems on the following page and the practice exam posted on the website
1. (14pts) Draw a mechanism to account for this reaction, including all arrows, intermediates,
and resonance structures.
How does your mechanism explain the observed regiochemistry of the product?
How does your mechanism explain why the reaction is an anti addition?
2. (16pts) Predict the major product(s) of 4 of the following 5 problems. Clearly mark the one
that you do not want graded or the first 4 will be graded. Include proper stereochemistry, and
indicate if both enantiomers are formed.
3. (4pts) The following reaction breaks the Markovnikov rule. Use the mechanism to explain
why the anti-Markovnicov product forms in this case.
4. (16pts) Provide the missing starting materials or reagents for 4 of the following 5 problems.
Clearly mark the one that you do not want graded or the first five will be graded.
5. (5pts) Provide a mechanism for this reaction.
6. (12pts) Provide all the reagents necessary for these multistep reactions.