Professional Documents
Culture Documents
SP 2010 Final Organic II 200pts (Weighted As 300)
SP 2010 Final Organic II 200pts (Weighted As 300)
If you do not want your graded exam placed outside my office, then please check here___
Good luck, I believe in you, you can do it, etc... 1) Identify the class of compounds that the following molecules belong to (8pts).
R C H O R C R O R C Cl O R C O-R O
R C NH2 O
R O H
R O O R
2) Draw Lewis structures (lone pairs are required) for the following classes of compound. (16pts)
Primary Amine
Alkyl Azide
Ether
Carboxylic Acid
Peroxy Acid
Alkyl Nitrile
Isocyanate
3) Circle a molecule in (1) or (2) with an SP hybridized atom. (1pt) 4) Put a cross through a compound in (1) or (2) which is relatively unstable and will decompose just above room temperature (1pt).
Sp10org2final
Page 1
5) Identify each of the below reactions either as a substitution, addition, elimination or condensation. (16pts)
CH2OH O (e) R R R
CHO OH R H
O (f) R R R
OH R OH O Cl R OH N-CH3 R R R
(g)
O R O R
(h)
Sp10org2final
Page 2
PERICYCLIC REACTION
KINETIC PRODUCT
8) State whether each of the following Molecular orbitals are overall bonding, antibonding or nonbonding (6pts).
(a)
(b)
(c)
Sp10org2final
Page 3
11) Indicate which of the following molecules are aromatic, non-aromatic or anti-aromatic. (Assume all the molecules are planar). (15pts)
+ O +
CH3 N
P N Mg-Br N
H H N+
12) Pick one of the above aromatic molecules, and use the polygon rule to demonstrate its aromaticity. (8pts)
Sp10org2final
Page 4
13) Give the products in six of the following reactions, paying attention to regio/stereochemistry where applicable. (18pts)
heat NC CN
Br
OH
1) NaOH 2) CH3CH2I
Ph C CH2 Ph
Br2, H2O
KOH
Excess HI O O
CH3 CO, HCl CuCl, AlCl3 NO2 1) Zn, HCl 2) NaNO2, HCl 3) CuCl, HCl CH3 Br2, uv light
Sp10org2final
Page 5
What is the hybridization of the Nitrogen atom (2pts?) 15) Write the mechanism for the formation of the nitronium ion NO2+ which is the active electrophile in nitration EAS reactions. (8pts)
H O O S O H O H O O N+ O_
NO2+
H2O
HSO4-
Sp10org2final
Page 6
16) Give reagents to accomplish five of the following transformations. (15pts) (Note that some require more than 1 step).
O O
CO2H
NO2
Cl
CO2H
CHO
F 3C
F 3C
O H 3C C
O C H
OH H 3C C H
O C H
Sp10org2final
Page 7
N (b) N H N CH3
(c)
NH2
NH
(d)
NH2
NH2
NH2
(e) O
N H
H N O H CH3 N O O
O N H
(f)
(b)
CH3CH2-O-O-H
CH3 CO2H
CH3CH2-O-H
(c)
CH3CO2H
H 2O
H2SO4
Sp10org2final
Page 8
CH3 CH3 O F O O
20) What two products are formed when an acid chloride is hydrolyzed by water ?
Sp10org2final
Page 9
21) Explain why nucleophilic ring opening of the below epoxide occurs with different regiochemistry in the two examples below. (9pts)
H2SO4, CH3OH
Sp10org2final
Page 10
22) Give the mechanism for two of the below conversions. (8 + 8pts)
NH2 (a) NaNO2, HCl + N N Cl-
O (b) Ph Ph
HOCH2CH2OH H2SO4
O Ph
O Ph
(c)
NH2
Sp10org2final
Page 11