F3CCF 3 - crab.rutgers.edualroche/su99org2e1.pdf · 5) Predict the products in the following...
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Organic II Exam #1 Ch 14-17 (100 points). NAME: 1) Aromatic compounds are defined as having planar structures, containing a certain number of electrons in a continuous overlapping cyclic arrangement of p orbitals. Name two characteristic physical or chemical properties of aromatic compounds. (3pts) 2) Indicate which of the following molecules are aromatic, non-aromatic or anti-aromatic. (Assume all the molecules are planar ). (20pts) + O N S F 3 C F 3 C CF 3 CF 3 CF 3 F 3 C O + P Org II Exam 1 Page 1
Transcript of F3CCF 3 - crab.rutgers.edualroche/su99org2e1.pdf · 5) Predict the products in the following...
Organic II Exam #1 Ch 14-17 (100 points). NAME: 1) Aromatic compounds are defined as having planar structures,
containing a certain number of electrons in a continuous overlapping cyclic arrangement of p orbitals. Name two characteristic physical or chemical properties of aromatic compounds. (3pts)
2) Indicate which of the following molecules are aromatic, non-aromatic
or anti-aromatic. (Assume all the molecules are planar). (20pts)
+O
N
S
F3C
F3C CF3
CF3
CF3F3C
O
+
P
Org II Exam 1 Page 1
3) Briefly explain your choices for the non-aromatic compounds (4pts) 4) Using the polygon rule, draw out and decide whether the following
species are aromatic or anti-aromatic. (12pts)
H H
H
+
_
_
_
(cyclopentadienideanion)
(cyclopropenyl cation)
(cyclo-octatriene dianion)
Org II Exam 1 Page 2
5) Predict the products in the following reactions (if you believe no reaction will occur, indicate this!), paying attention to regio/stereochemistry where applicable. (19pts)
O CH2CH2CH3Excess HI
OO
Excess HBr
CF3F3Cheat
S CN heat
C CH2
H3C
H3C
Cl2, H2OA KOH B
NO2
Cl2, AlCl3
CH2CH3
CH2CH3
HNO3, H2SO4
Org II Exam 1 Page 3
6) Both pyrrole and pyridine are nitrogen containing heterocycles that are 6π Hückel aromatic.
HN
N
The lone pair on nitrogen plays a different role in each molecule's aromaticity, and consequently pyridine is a strong base and pyrrole is a weak base. Pick either pyrrole or pyridine and describe the aromaticity and observed basicity for that molecule. (15pts)
Org II Exam 1 Page 4
7) Give reagents and conditions to accomplish the following transformations. (17pts)
CH2CH3
CH2CH3
CO2H
CO2H
CH2-OH CH2-O-CH2
O
OH3C
Ph PhH
HO
PhH3C
PhPh
H
A CH2CH2CH2CH3
(no marks for A)!!!
Br
Org II Exam 1 Page 5
8) The addition of (1 equivalent of) DCl to 1,3-cyclohexadiene generates a mixture of products.
raw the products, and mechanistically account for the mixture of products. (10pts)
D
D-Clmixture
Org II Exam 1 Page 6
*Bonus question* (2pts!!!) Based on arguments of aromaticity, would you expect the following compound to be one of the world's strongest acids or one of the world's strongest bases?
F3C
F3C CF3
CF3
CF3H
Org II Exam 1 Page 7
