Houseknecht
Chem 201
Fall 2012
Name_____________________________________
I _______________________________________ (sign name) affirm that my work upholds the highest
standards of honesty and academic integrity at Wittenberg, and that I have neither given nor
received any unauthorized assistance.
There are 6 pages (including this one) and 10 questions on this exam. Read each question carefully before
beginning. Show work for partial credit. A periodic table is attached to the end of this exam. You may
remove it and use it for scrap paper. You may also use the lower portion of this cover page as scrap paper.
If you would like any more scrap paper please ask. Good luck.
Houseknecht
Chem 201
Fall 2012
Exam 2 – October 9, 2012
1. (20 pts) Provide the IUPAC name or structure of the following compounds. Indicate stereochemistry
if relevant.
Structure
Name
Houseknecht
Chem 201
Fall 2012
2. (6 pts) Circle the highest priority groups on each of the alkene carbons below and indicate whether
each alkene is E or Z.
3. (4 pts) Calculate the degrees of unsaturation present in a molecule with the molecular formula
C5H9NO2 and draw one possible structure.
4. (6 pts) Provide curved arrows to show how electrons move in the following reactions:
5. (4 pts) Identify one electrophilic and one nucleophilic site in testosterone.
Houseknecht
Chem 201
Fall 2012
Houseknecht
Chem 201
Fall 2012
Energy
6. (6 pts) Label a transition state (TS) and an intermediate (I) for the reaction represented by a dashed
line below.
Reaction Progress
a. Indicate which product (solid or dashed) would be favored if the reaction was reversible and
explain your rationale.
b. Indicate which product (solid or dashed) would be favored if the reaction was irreversible and
explain your rationale.
7. (6 pts) Provide at least six unique statements explaining why only the products shown below are
formed and why the major product is favored. Chemical structures will be important.
Houseknecht
Chem 201
Fall 2012
8. (10 pts) Reaction of the alkene below with HBr yields three products. Indicate how the first two
products are formed using curved arrows to indicate electron flow for the cleavage and formation of all
bonds. Also, explain why the minor product is not preferred.
9. (8 pts) Indicate how trans-1,2-dichlorocyclohexane is formed in the reaction below using curved
arrows to indicate electron flow for the cleavage and formation of all bonds. Also, explain why the
cis-1,2-dichlorocyclohexane is not observed.
Houseknecht
Chem 201
Fall 2012
10. (30 pts) Provide the major and minor organic products of the following reactions. If a reaction
would not proceed, write “no reaction”. Indicate stereochemistry where important.
Extra Credit (5 pts) A hydrocarbon of unknown structure has the formula C8H10. On catalytic
hydrogenation over Lindlar’s catalyst, 1 eq. of H2 is absorbed. On hydrogenation over Pd/C, 3 eq of H2 are
absorbed.
How many degrees of unsaturation are present in the unknown?
How many triple bonds are present?
How many double bonds are present?
How many rings are present?
Draw a structure that fits this data.