Organic Chemistry I Final Exam
I.
Multiple Choice: Select all answers for each question (mark circles)
1 pt for the right answer but -0.25 pt for the wrong one
1. The regiochemistry of hydroboration/oxidation of
alkenes is ( a. Markovnikov. b. non-Markovnikov c.
Hoffmann product. d. Zaitsev product.
2. When 3-methyl-pentan-3-ol is with HCl/ZnCl2, 3-chloro-3-methylpentane is the major
organic product. This reaction proceeds through an ________ mechanism, and
________ is produced as a byproduct.
A) S 1,H O B) S 2,H O C) E1, HO
N 2 N 2 2
D) S 2, H E) E2, H O
N 2 2
3. Which is proton in the circle compound most acidic?
4. What is the best choice of reagent(s) to perform the following transformation?
Br
OH
(a) Hg(OAc)2, H2O, THF; followed by NaBH4 (b) NBS, H2O in DMSO
(c) BH3; followed by H2O2, H2O, NaOH (d) H2O, H2SO4
, 5. Which of the following conformation energies of butane contribute to the
statement that the g conformer is more stable than the gauche one?
1, torsional stain; 2, steric strain; 3, angle strain
(a) 1 (b) 2 (c) 3 (d) none of above
6. Which of the following is the most stable radical?
7. What is the product of the following reaction?
8. When petroleum is distilled, the fraction that contains compounds with
5 to 11 carbons is known as ________.
A) natural gas B) asphalt
C) diesel oil D) gasoline E) jet fuel
9. Which of the following terms is the best description for the pair of compounds?
OH O
(a) diastereomers (b) enantiomers (c) tautomers (d) resonance
10. How many signals would you expect to see in the 1H NMR spectrum
of the following compound?
A) 2 B) 5 C) 1
D) 4 E) 3
I.
Multiple Choice: Select all answers for each question (mark circles)
1 pt for the right answer but -0.25 pt for the wrong one
1. The regiochemistry of hydroboration/oxidation of
alkenes is ( a. Markovnikov. b. non-Markovnikov c.
Hoffmann product. d. Zaitsev product.
2. When 3-methyl-pentan-3-ol is with HCl/ZnCl2, 3-chloro-3-methylpentane is the major
organic product. This reaction proceeds through an ________ mechanism, and
________ is produced as a byproduct.
A) S 1,H O B) S 2,H O C) E1, HO
N 2 N 2 2
D) S 2, H E) E2, H O
N 2 2
3. Which is proton in the circle compound most acidic?
4. What is the best choice of reagent(s) to perform the following transformation?
Br
OH
(a) Hg(OAc)2, H2O, THF; followed by NaBH4 (b) NBS, H2O in DMSO
(c) BH3; followed by H2O2, H2O, NaOH (d) H2O, H2SO4
, 5. Which of the following conformation energies of butane contribute to the
statement that the g conformer is more stable than the gauche one?
1, torsional stain; 2, steric strain; 3, angle strain
(a) 1 (b) 2 (c) 3 (d) none of above
6. Which of the following is the most stable radical?
7. What is the product of the following reaction?
8. When petroleum is distilled, the fraction that contains compounds with
5 to 11 carbons is known as ________.
A) natural gas B) asphalt
C) diesel oil D) gasoline E) jet fuel
9. Which of the following terms is the best description for the pair of compounds?
OH O
(a) diastereomers (b) enantiomers (c) tautomers (d) resonance
10. How many signals would you expect to see in the 1H NMR spectrum
of the following compound?
A) 2 B) 5 C) 1
D) 4 E) 3
