1st FINAL EXAMINATION OF

ORGANIC CHEMISTRY II

Times: 90 minutes May 28th, 2014

Answer the questions correctly!

1. Using flow equations, show how each of the folowing compounds could be prepared starting
with either malonic ester or acetoacetic ester:
O
H3C
a). CH3CCHCH2CH2CH3 b). (CH3CH2)2CHCO2H c). CO2H
H3C
CH2CH3

2. A primary amine was subjected to exhaustive methylation. The resulting quaternary ammonium
salt was heated with silver oxide/water to give trimethylamine and an alkenes. Ozonolysis and
workup of the alkene yielded acetone as the only organic product. Explain a structure for amine.

3. Deduce the structure of compound of formula C3H10N2 that is obtained by treating 1,3-
dibromopropane with potassium phtalimide, followed by treatment with hydrazine and water.

4. When D is treated with excess iodomethane, a quaternary salt is formed. Heating this salt with
silver oxide/water yields E, of formula C7H15N. Compound E is also converted into a quaternary
salt on treatment with excess iodomethane. Heating this quaternary salt with silver oxide/water
yields F, of formula C5H8. Suggest the structure for compounds D, E, and F with mechanism
reaction.

5. When 1-nitronaphtalene is treated with CrO3 in CH3CO2H, a product of formula C8H5O6N is

formed. Explain a structure for this product.

6. Predict the organic products and explain the major organic product (if no reaction occurs, write no
reaction)
O

Cl
a). + AlCl3

OH

b). + HNO3

7. Predict the electrocylic product and its stereochemistry:

kalor h
a). b).
 1st FINAL EXAMINATION OF
ORGANIC CHEMISTRY II

Times: 90 minutes May 28th, 2014

Answer the questions correctly!

1. Using flow equations, show how each of the folowing compounds could be prepared starting
with either malonic ester or acetoacetic ester:

O
H3C
a). CH3CCHCH2CH3 b). (CH3CH2)2CHCO2H c). CO2H
H3C
CH2CH3

2. A primary amine was subjected to exhaustive methylation. The resulting quaternary ammonium
salt was heated with silver oxide/water to give trimethylamine and an alkenes. Ozonolysis and
workup of the alkene yielded acetone as the only organic product. Explain a structure for amine.

3. Deduce the structure of a compound of formula C7H9N that is obtained by treating benzonitrile
with hydrogen in the present of palladium in dilute HCl and ethanol.

4. When D is treated with excess iodomethane, a quaternary salt is formed. Heating this salt with
silver oxide/water yields E, of formula C7H15N. Compound E is also converted into a quaternary
salt on treatment with excess iodomethane. Heating this quaternary salt with silver oxide/water
yields F, of formula C5H8. Suggest the structure for compounds D, E, and F with mechanism
reaction.

5. When 1-nitronaphtalene is treated with CrO3 in CH3CO2H, a product of formula C8H5O6N is

formed. Explain a structure for this product.

6. Provide the structure for this organic products of each of the following reactions.

NH3
a).
kalor

N Br

HNO3
b).
N H2SO4 (0o)

7. Classify each of the following sigmatropic rearrangements as [1,3], [3,3], etc

a). H
kalor

b). kalor

H CH3
CH3

Good luck