TUTORIAL 3: HETEROCYCLIC

COMPOUNDS
1. Name each of the following compounds referring to the given table.

N
N
(iii)
(i) (ii)
N O
S

(iv) CH3
(v)
H H
N CH3 N
H

H2 N O
N
(vii)
(vi)
N

Ring Containing Nitrogen Ring Without Nitrogen

Ring Unsaturated One double Saturated Unsaturated One double Saturated
bond bond
3 -irine -iridine -irene -irane
4 -ete -etine -etidine -ete -etene -etane
5 -ole -oline -olidine -ole -olene -olane
6 -ine -in -ane
7 -epine -epine -epane
8 -ocine -ocin -ocane
9 -onine -onin -onane
10 -ecine -ecin -ecane

2. The reaction of aromatic electrophilic substitution for pyridine normally occurs at

C3. Draw an intermediate carbocation structure resulting from an electrophilic
attack on C1, C2, and C3 and explain in detail the reaction that occurred.

3. Write an equation for the reaction between furan with the following reagents:

a. Br2, dioxane, 0c b. HNO3, acetic anhydride c. CH3COCl, SnCl4

d. H2/Pd e. SO3, pyridine
4. Pyrrole has a dipole moment of = 1.8D where the nitrogen atom is situated at
the end of the positive dipole. Explain.

5. If 3-bromopyridine is heated with NaNH2, a mixture of 3- and 4-aminopyridine is

produced. Explain.

6. Show how the following synthesis is done. Synthesis may require more than one
step.

(i)
SO3H
N N
H H

(ii)
CHO
O O

(iii)
N
O H

(iv) C=O
N H
N H
H

7. Name the following structures:

NO2
N
(ii) (iii)
(i)
Br CH3 Br N
S N
H OCH3

8. Using the nitration of pyrrole reaction as an example, predict whether that

reaction occurs at C-2 or C-3. Write the equations of the reactions in detail.

9. Write all the resonance structures for the intermediate cations produced from the
reaction of pyridine with electrophile E+ at C-2, C-3, and C-4 and with that,
explain the orientation of this reaction. (That is, explain the substitution of the
more favored carbon)