Final Exam for Organic II 200pts(Weighted as 300)
Final Exam for Organic II
200pts(Weighted as 300)
Name
Good luck all round!
1) Identify the class of compounds each of the following molecules belong to (15pts).
ROH
ROR
R CN
O RCH
O R C NR2
O R C O-R
OO RCOCR
H
O
N C
O
O R C O-H
2) For each of the amides and amines state whether they are primary, secondary or tertiary (4pts).
3) Circle one of the above compounds that is reactive enough to react with neutral water (2pts).
4) Give two characteristic physical or chemical properties of aromatic compounds (4pts).
Final Exam for Organic II
Page 1
5) Indicate which of the following molecules are aromatic, non-aromatic or anti-aromatic. (Assume all the molecules are planar). (15pts)
HH
O
H3C H3C
CH3 CH3
+ O
N+
H3C
CH3
N S
NO2
N NO2
N
+
6) Pick one of the above antiaromatic molecules, and use the polygon rule to demonstrate its antiaromaticity. (8pts)
Final Exam for Organic II
Page 2
7) Give the products in six of the following reactions, paying attention to regio/stereochemistry where applicable. (18pts)
heat
NC
CN
O CH2CH2CH3
Excess HBr
A Ph
C CH2
Br2, H2O
Ph
KOH
B
O O
Excess HI OH
F CN
CO, HCl CuCl, AlCl3
heat
CH3 NHCOCH3
Br2, FeBr3
Final Exam for Organic II
Page 3
8) The below heterocycle contains two Nitrogen atoms, and is 6 H?ckel aromatic.
CH3 N
N
The lone pairs on the two Nitrogens play different roles in the aromaticity of the molecule, and consequently one Nitrogen will get protonated before the other.
Describe which one gets protonated first, and explain their differing basicity. (10pts)
Final Exam for Organic II
Page 4
9) Give reagents and conditions to accomplish five of the following transformations. (15pts)
CH3
CH3 O
O2N
CH2-OH
O
H3C
H
Ph Ph
CH2CH3
CH3CH2
CH2CH3
O2N
CH2-O-CH2
NO 2
HO H
H3C
CH2CH2CH3
Ph Ph
CO2H
HO2C
CO2H
O
Br O
A
Final Exam for Organic II
CH2CH2CH3 (no marks for A)!!!
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