1 Name: _______________________________________________________________________ Last First MI Section # _____________ PID# ___________________ Equation: ΔG 0 = −RT ln Keq • ΔG 0 = Change in Gibbs free energy • Keq = Equilibrium constant • T = Temperature in kelvins • R = Universal gas constant that has the value 8.314 J (1.987 cal)·K −1 ·mol −1 Electronegativity Values: F 4.0 O 3.5 N 3.0 Cl 3.0 Br 2.8 C 2.5 S 2.5 I 2.5 P 2.1 H 2.1
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Name: _______________________________________________________________________ Last First MI Section # _____________ PID# ___________________
Equation: ΔG0 = −RT ln Keq • ΔG0 = Change in
Gibbs free energy • Keq = Equilibrium
constant • T = Temperature in
kelvins • R = Universal gas
constant that has the value 8.314 J (1.987 cal)·K−1·mol−1
Electronegativity Values: F 4.0 O 3.5 N 3.0 Cl 3.0 Br 2.8 C 2.5 S 2.5 I 2.5 P 2.1 H 2.1
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Name: _______________________________________________________________________ Last First MI Section # _____________ PID# ___________________
Grading Page (Final Exam):
Page Points Possible Points Earned
3 20
4 16
5 20
6 31
7 44
8 20
9 30
10 20
Bonus 20
TOTAL 201 + 20
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1. (20 pts) Mometasone furoate is the active component of the Asmanex ® Twisthaler ®, which is used to keep the symptoms of asthma under control.
A. Circle all of the terms below that describe one or more structural features of Mometasone furoate.
1° Alcohol Alkene Non-aromatic ring
2° Alcohol Amide Ester
3° Alcohol Aromatic ring Epoxide
Amine Halide Ketone
Heteroaromatic ring Ether Aldehyde
B. In the boxes above, give the stereochemical designation (R or S) for the indicated chiral centers.
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2. Acids and bases (16 pts)
A. For each pair of compounds shown below, select the more acidic of the two compounds and explain your reasoning in under ten words. (2 points each)
B. For each of the following reactions, does the equilibrium favor the reactants or products? (2 point each)
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3. (20 points) Describe each of the following pairs of molecules as identical, enantiomers, diastereomers, or constitutional isomers.
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4. (15 points) Draw the following molecules in both chair confirmation and circle the most stable.
5. (40 points) Predict the products of the following reactions. (4 points each)
a.
b.
c.
d.
a.
b.
c.
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e.
f.
g.
h.
i.
j.
Na, liq. NH3
6.
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7. Show a reasonable arrow-pushing mechanism for these reactions. (10 points)
a.
b.
Predict the product of the following reaction and show a reasonable arrow-pushing mechanism for these reactions. (6 points)
8. (40 pts) Give a synthetic route for the following transformations. You may use any reagents you like. (10 points each)
a.
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b.
1-bromo-2-methylcyclopentane from methylcyclopentane
c.
2,2-dibromopropane from 1,2-dibromopropane
d.
2-butyne from 1-butyne
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9. Show a mechanism for this reaction (ignoring stereochemistry), and draw a box around the final product. Clearly label your initiation, propagation and termination steps, and show at least two examples of termination. (20 points)
Bonus: 20 points
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