North Maharashtra University 2009 B.Sc Chemistry of Heterocyclic & Polycyclic Compounds - Question Paper

*Chemistry of Heterocyclic & Polycyclic Compounds*

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ques. for two marks.
1) describe the subsequent
a. Heterocyclic compound
b. Polycyclic compound
2) Draw the resonance structure for the subsequent.
a. Naphthalene
b. Benzene.
3) Predict the product.
a. Furan H2/ Ni ?
b. Thiophene CH3COCl/ AlCl3 ?
c. Thiophene CHCl3/KOH ?
d. Thiophene H2/Ni ?
e. Pyrrole CHCl3/KOH ?
f. Pyrrole H2/Ni ?
g. Pyridine H2SO4/3500C ?
h. Napthalene CrO3/AcOH ?
250C

i. Napthalene O2/V2O5 ?
460-4800C
j. Napthalene Conc. H2SO4 ?
1600C
k. Napthalene Cl2 ?
l. Napthalene HNO3/H2SO4 ?
50-600C
m. Napthalene H2SO4 ?
800C
n. Napthalene H2/Pt ?
o. Napthalene CH3COCl ?
AlCl3/CCl4
p. Pyridine H2/Pt ?
250C,3 atm.
q. Pyridine HNO3/H2sO4 ?
3000c
r. Furan SO3/pyridine ?
s. Pyridine Br2 ?
3000c
t. Pyrrole H2SO4 ?
u. Pyrrole CH3COCl/AlCl3 ?
v. Thiophene H2SO4 ?
w. furan CHCl3/KOH ?
4) select the accurate option of subsequent.
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a. TheC1—C2 bond length in Napthalene is------
1)1.365 A0
2)1.412A0 3)1.464A0 4)1.394A0
b. The C2—C3 bond length in Napthalene is------
1)1.390A0 2)1.404A0 3)1.363A0 4)1.425A0
c. Napthalene on Sulphonation by conc. H2SO4 at 800c provide –
1) a—napthalene Sulphonic acid 2) ß—napthalene Sulphonic acid
3) ?—napthalene Sulphonic acid 4) d––napthalene Sulphonic acid
d. Napthalene on Sulphonation by conc. H2SO4 at 1600c provide –
1) a—napthalene Sulphonic acid 2) ß—napthalene Sulphonic acid
3) ?—napthalene Sulphonic acid 4) d––napthalene Sulphonic acid
e. Napthalene on reaction with CH3COCl & AlCl3 in presence of solvent carbon
tetrachloride give-----
1) 2-aceto napthalene 2) 1-aceto napthalene
3) 3-aceto napthalene 4) 4-aceto napthalene
f. Napthalene on reaction with CH3COCl & AlCl3 in presence of solvent Nitrobenzene
give-----
1) 2-aceto napthalene 2) 1-aceto napthalene
3) 3-aceto napthalene 4) 4-aceto napthalene
g. Furfural on steam distillation give------
1) Thiophene 2) Furan 3) Pyrrole 4) Pyridine
h. Thiphene undergoes electrophilic substitution reaction at position number----
1) two 2) three 3) four 4) 5
i. Pyridine undergoes electrophilic substitution reaction at position number----
1) two 2) three 3) four 4) 1

ques. for three marks.
1) explain the structure of Napthalene.
2) Napthalene is aromatic in nature, discuss.
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3) Electrophilic substitution reaction in Pyridine takes place at position no 3.
Explain.
4) What is the action of subsequent reagent on Pyridine? provide balance eq”.
a. H2/Ni b. Br2/3000c c. H2SO4/3500c.
5) What is the action of subsequent reagent on Napthalene? provide balance eq”.
a. conc. H2SO4/800c b. H2/Pt
c. HNO3/H2SO4,50-600c. d. Br 2
e. conc. H2SO4/1600c f. Na/C5H11OH, Reflux.
g. O2/V2O5, 460—4800c h. CrO3/ACOH, R. T.
6) provide the reaction of KOH/CHCl3 on----.
a. Thiophene
b. Pyrrole
c. Furan.

ques. for four marks.
1) provide the Haworth’s synthesis of napthalene.
2) How will you synthesize Furan from mucic acid & furfural?
3) provide 2 methods of preparation of Pyrrole.
4) provide 2 methods of preparation of Thiophene.
5) provide 2 methods of preparation of Pyridine
6) How will you convert napthalene into -----
a. 1, four –Naptha quione.
b. Decalin.
c. ß—Napthalene sulphonic acid.
d. a––bromonapthalene.
7) How will you convert subsequent.
a. Pyridine into piperidine.
b. Pyrrole into pyrrolidine.
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c. Furan into furfural.
d. Thiophene into 2-benzoyl Thiophene.
e. Pyrrole into 2-pyrrole Sulphonic acid.
f. Acetylene into pyridine.
g. Pentamethylene diamine into pyridine.
h. Furfural into furan.
i. Acetylene into pyrrole.
j. Acetylene into thiophene.

ques. for six marks.
1) explain the structure of napthalene. provide its canonical structures.
2) provide the Haworth’s synthesis of napthalene & discuss in napthalene C1-C2 bond
length is shorter than C2-C3.
3) elaborate hetero cyclic compounds? provide 1 method of synthesis ofa.
Furan b. Thiophene c. Pyrrole d. Pyridine
4) provide the Haworth’s synthesis of napthalene. Napthalene is aromatic in nature,
explain.
5) discuss sulphonation of napthalene at various temperature. Why ß-isomers
predominates at high temp.?
6) provide synthesis of Thiophene, pyrrole & pyridine from acetylene.

Earning:   Approval pending.