C 202 Organic II
Test 1
February 8th, 2007
I.
Identify (2 pts each)
Markovnikov’s rule, homolysis, radical, hydrogen abstraction, propagation step,
Regioselective reaction, Stereospecific reacion, co-polymer, syndiotactic, isotactic,
atactic,
II.
Polymer Chart. Fill in each open cell. (1 pts each)
Monomer
Polymer
Names
Polystyrene
n
Cl
Cl
Cl
PVC
n
Polyacrylonitrile
NC
F
F
F
F
F
F
F
F
F
F
F
F
F
F
n
F F
COOCH3
COOCH3
COOCH3
H 3C
CH3
CH3
Poly
(methylmethacrylate)
n
III.
Nomenclature (3 pts each)
A. Name the following:
OH
Cl
B) Give the structure of (2S)-2-Chlorohex-3-yn-1-ol
IV.
Reactions (3 pts each)
Provide the product(s) for the reactions below:
NBS
A)
D)
C
H3 CH2CH 2C
Cl
B)
CH3
H
CH2 CH3
Br2

G)
1) OsO 4
2) NaSO 3 / H2 O
1) O3
E)
2) Zn / HOAc
H)
1) O3
2) Zn / HOAc
HBr
C)
1) KMnO 4, -OH
heat
F)
ROOR
2) H3 O
+
I)
Br2
H2 O
1) BHtotal)
3 :T HF
V.
Mechanisms (12 pts
A)
(8
pts)
Provide the product(s) for the
below and the mechanisms that account for
2 ) H2reactions
O2 , -O H
each product.
A)B) (4 pts)
+ Br2

B)C) (8 pts) Provide a mechanism for the polymerization of ethene. Be sure to include and label
special cases such as combination, disproportionation, and backbiting in the appropriate
steps.
VI.
Synthesis (10 pts total)
A) Provide a retrosynthetic pathway for the synthesis of 2-bromobutane from
compounds of 2 carbon atoms or less. (5 points)
B) Provide a retrosynthetic pathway for the synthesis of 1,2-pentandiol from
compounds of 2 carbon atoms or less. (5 points)
VII. Essay. (10 pts)
Write a brief essay describing polymerizations including such terms as: Chaingrowth/addition polymers, Cationic polymerizations, Anionic polymerizations,
copolymer, atactic, syndiotactic, and isotactic. You should also include examples.
VIII. NMR/MS (15 points)
A. The compound CH3F, gave peaks in a mass spectrum at 14, 15, 19, 31,
32, 33, 34, 35 with the following relative intensities 17.2, 100, 2.0,
10.4, 9.4, 89.5, 95.4, and 1.1 respectively. Provide a structure for each
of the ions associated with those peaks and show how they were
formed. (the peak at 34 is the molecular ion peak) (7 points)
B. Using the following Molecular formulas, NMR data, and/or IR data,
provide the structure of the molecule.
i. C4H8O NMR: triplet at 1.05 (3H), singlet at 2.13 (3H), quartet
at 2.47 (2H). IR: Stong peak near 1720 cm-1 (4 points)
ii. C4H7BrO2 NMR: triplet at 1.25 (3H), multiplet at 2.07 (2H),
triplet at 4.23 (1H), singlet at 10.97 (1H). IR: broad peak in
2500-3000 cm-1 region and a peak at 1715 cm-1 (6 points)