Name _________________________________

ID# ___________________________________

Please check the box if you do NOT wish to have your exam returned in class. Exams not
returned in class can be picked up individually at my office during office hours (Kolthoff
468A).

Exam II
Organic Chemistry 2302-01
Fall 2014
6 pages including Periodic Table

Do not open the exam until you are asked to do so.

Place your last name on all subsequent pages in case pages get separated.
Raise your hand if you have a question and a TA or I will help you.
Regrades will only be considered for exams written in PEN.
You may NOT use calculators, models, or any notes for this exam.
Exam begins at 10:10 a.m. and ends at 11:00 a.m.
When time is called by the TAs, all pens are to be down and no more written work done. TAs are
authorized to deduct 5 points from the exam of any student that does NOT following these rules.
Read all questions carefully and be sure to answer each individual question. Circle only ONE answer
for multiple choices type problems for full credit.
Good luck!

1)

_________/ 18 pts

2)

_________/ 26 pts

3)

_________/ 30 pts

4)

_________/ 26 pts

Total

_________/ 100 points

Last Name ____________________________

1. Acidities and Equilibrium. For each acid-base reaction/hydrate formation reaction below, draw the product(s)
of the reaction and then indicate which direction the equilibrium lies based on the relative acidities or
equilibrium by circling the word RIGHT or LEFT. pKa values are not needed since each problem represents a
concept we have learned about relative acidities or reactivity.
12 pts

2. Functional Group Recognition. Consider the molecule below. Identify each of the following functional
groups, if present, by circling the appropriate group of atoms and neatly writing the word or letter. There may
be more than one for each functional group or NONE. Plus points for correct answers, minus for incorrect.
6 pts
A. carboxylic acid
B. aldehyde
C. ketone
D. ester
E. acetal

F. hemiacetal

G. imine

I. enamine

J. amide

_____

18 pts
Wissinger, Chemistry 2302-01, Fall 2013, Page 1

Last Name ____________________________

3. Roadmap Problem Complete the roadmap problem below by either supplying the missing reagents or
products. For reagents, be sure to specify distinct steps with 1) and 2) etc if appropriate. If necessary, work
backwards to complete all transformations. Be sure to count carbons.
18 pts

4.

Mechanisms Draw a step-wise mechanism for each reaction below using proper arrow notation and showing
all intermediates, including proton transfers (that is do not just write proton transfer.
8 pts

______

26 pts
Wissinger, Chemistry 2302-01, Fall 2013, Page 2

Last Name ____________________________

Mechanisms, continued.
6 pts

5. Contrasting Reactions Draw products for each reaction below, one to the right and one to the left, for the
center molecule. Show stereochemistry where requested. Indicate if NO REACTION will occur.
a.
6 pts

b.

6 pts

c.

6 pts

d.

6 pts

______
30 pts
Wissinger, Chemistry 2302-01, Fall 2013, Page 3

Last Name ____________________________

Contrasting reactions continued
e.

6 pts

f.

6 pts

g.

6 pts

6.

Multi-Step Synthesis. Propose a synthesis of the compound below starting with 2 molecules of
cyclohexanol and any other organic or inorganic compounds you need. Show all intermediates.
8 pts

THE END
_____
26 pts
Wissinger, Chemistry 2302-01, Fall 2013, Page 4

Last Name ____________________________

Wissinger, Chemistry 2302-01, Fall 2013, Page 5