Chem 140C Summer 2016 Practice Final Exam Answer Key
Chem 140C Summer 2016 Practice Final Exam Answer Key
Chem 140C Summer 2016 Practice Final Exam Answer Key
Total_________(300 points)
If you write the exam in pencil or erasable pen, you give up your right to any kind of regrade.
Name _________________________
PID# __________________________
B. Circle the most acidic hydrogens (or hydrogens) in each molecule below and place them in order
of their acidity with #1 being the most acidic and #4 being the least acidic. Work carefully.
There will be no partial credit or regrades on this problem.
Note: The acidic hydrogens may not be showing on the drawing.
B. Place the following compounds in order of their basicity with #1 being the most basic and #4
being the least basic. Work carefully. There will be no partial credit or regrades on this problem.
B. Place the following molecules in order of their reactivity with CH3S Na+ via an SnAr mechanism.
Label the most reactive as #1 and the least reactive as #4. Work carefully. There will be no partial
credit or regrades on this problem.
4. Chemical Reactions - Give the Product (-- points). Draw the organic products of the following
reactions. Indicate stereochemistry where appropriate. A reasonable answer may be No Reaction.
1)
N C N
/ Et3N
O
H
N
tBuO
OH
O
G.
H 2N
O
OCH2Ph
N
H
O
H
N
tBuO
O
2) H2 / Pd
N
H
OH
N
5. Chemical Reactions - Give the Reactant(s) (-- points). Draw the reactants of the following
reactions. Indicate stereochemistry where appropriate.
6. Methodology (-- points). Show with equations three ways to make a secondary amine starting
from a primary amine or a tertiary amine. Your 3 methods must use different reactions to either
make the new C-N bond or break a C-N bond.
7. Reaction Mechanisms (-- points, maximum). Draw reasonable mechanisms for the reactions
below. Do 2 of 3 and clearly indicate which you want graded. Note that Part A is worth points, Part B is worth -- points and Part C is worth -- points.
A.
B.
B. Show how you would synthesize the dipeptide GlyAlaPhe starting from Phe, Gly and Ala and any
other organic or inorganic reagents.
Lots of ways to approach this. The best advice is: Write down whatever you can to show the
grader and me that you know what you are talking about. This will be judged on both quantity and
quality.