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Provide IUPAC names for the following compounds (don't forget stereochemistry where appropriate). (20 points). 2. Draw the structure of the following ...
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CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3, practice Page 1 of 8
a. ( R )-2-(2-oxopropyl)nonanedial
b. hexanal dimethyl acetal
c. (1 S ,3 R )-3-(2-propenyl)cyclopentanecarboxylic acid
d. benzaldehyde oxime
CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3, practice Page 2 of 8
p-TsOH
(catalyst)
O O
O
1,3-propanediol
CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3, practice Page 4 of 8
CHO
NO 2
O
N H
O (^) H+
H 3 CO
O
a.
b.
c.
H 2 N NHCH 3
NaOH
CO 2 H
CO 2 H
H 3 C OH
O
OH
O CH 3 O
CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3, practice Page 5 of 8
EXTRA CREDIT Provide IUPAC names for the starting material and the product. (10 EC points)
O
O
CH 3 OH
O
O O
O
O O
O CH 3
CH 3 O
HO
CH 3 CH 3
O
H
CH 3
OH
H
H
O
I
O
OH
CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3, practice Page 7 of 8
Mass spectrum (M+^ = 162 m/z )
(^1) H and 13 C NMR are attached but expanded views of the 1 H NMR are below.
CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3, practice Page 8 of 8
Alternate 13 C NMR spectrum (doesn’t show the solvent peak)
(^13) C NMR peak list (ppm)
