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I.
Nomenclature
1.
Protoapigenone, shown below, is a flavanoid compound having cytotoxic activity
against several types of cancer (J. Med. Chem. 2007, 3921). Circle and identify
each different functional group in protoapigenone. (5 points)
2.
Provide a structure for each of the following compounds. (5 points)
neopentane
3.
spiro[5.4]decane
Identify the correct IUPAC name for the following structure. (9 points)
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II.
4.
The following bile acid derivative has shown potent ability in regulating the
immune system and cholesterol levels, and lipid and carbohydrate metabolism (J.
Med. Chem. 2007, 4265-4268). Circle all primary (1o) carbons in the structure
below. (3 points)
5.
How many degrees of unsaturation are there in the structure above? (2 points)
6.
An unknown compound was found to have 5 carbons, 1 ring, and only a nitrile
and an ester functional group. Provide a molecular formula for the unknown
compound. (3 points)
Theory
1.
Provide a Lewis structure for CH3NCO. (2 points)
2.
How many sigma bonds are there in the structure from question #1? (2 points)
3.
Fill in any missing formal charges in the structure below, and then circle all sp2
centers. (6 points)
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4.
Provide two other significant resonance structures for the following structure.
Indicate any formal charges and circle the major contributor to the overall
resonance hybrid. (8 points)
5.
Draw all isomers of C3H9N and circle the structure that has the highest boiling
point. (10 points)
6.
State all intermolecular attractions present in pure samples of each of the
following structures. (6 points)
H2SO4
7.
BF3
CH3CO2CH3
Translate the following line-angle structure to a condensed structure. (3 points)
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8.
Draw the structure represented in the Newman projection below as a wedge-dash
perspective structure. (3 points)
9.
Between the C2-C3 bond of butane, how much higher in energy (Kcal/mol) is the
eclipsed conformation than the anti conformation? (2 points)
10.
Draw the structure below in its most stable chair conformation. Label all
substituents as equatorial or axial. (5 points)
11.
With each structure in its most stable chair conformation, which sequence
correctly ranks the compounds below in order of increasing molecular dipole
moment?(3 points)
1) trans 1,4-dichlorocyclohexane
2) trans 1,3-dichlorocyclohexane
3) trans 1,2-dichlorocyclohexane
a) 1<2<3
12.
b) 2<3<1
c) 3<1<2
d) 3<2<1
e) 2<1<3
f) 1<3<2
Which sequence ranks the following structures in order of increasing acidity? (3
points)
a) 1<2<3
b) 2<3<1
c) 3<1<2
d) 3<2<1
e) 2<1<3
f) 1<3<2
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13.
Which sequence ranks the following compounds in order of increasing basicity?
(3 points)
a) 1<2<3
III.
b) 2<3<1
c) 3<1<2
d) 3<2<1
e) 2<1<3
f) 1<3<2
14.
Shown below is an energy diagram for the valance electrons of an unhybridized
carbon atom. Provide a new energy diagram to represent an sp hybridized carbon
atom. (2 points)
15.
Draw the two molecular orbitals that would result from the combination of two
atomic p orbitals. (4 points)
16.
What factor of ring strain is present in cyclononane but not in cyclopropane? (2
points)
IR spectroscopy
1.
Indicate all functional groups represented in each IR spectra below? (9 points)
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IV.
Extra Credit (5 points)
1.
Translate the following Newman projection to a bicyclic chair structure. Label all
substituents as being equatorial or axial.
You received __________ points out of 100 points possible. To check your overall performance
in lecture see http://vista.weber.edu/.