1

Polynuclear Aromatic Hydrocarbons

Questions
1. (a) Draw the structure of naphthalene with the numbering of all carbon atoms
and answer the following questions: 1
(i) Draw the all possible resonance structures of naphthalene. 1
(ii) Is naphthalene a bridge or fused ring bicyclic compound? 0.5
(iii) Is naphthalene an aromatic compound? Give explanation in support
of your answer. 2
(iv) Are all the carbon-carbon bond lengths in naphthalene same? Give reason in
support of your answer. 3
(b) Give a method for the preparation of​ ​naphthalene.​ ​4.5
(c) What product would you expect to be formed when naphthalene is treated with
(i) H​2​SO​4​ at 80​o​C (ii) Br​2 ​ 2

2. (a) “Naphthalene undergoes oxidation and reduction reactions more readily than
benzene”- How will you explain the statement? 3
(b) “Anthracene and phenanthrene are more reactive toward the electrophilic
substitution reaction than benzene”- How will you explain the statement? 3
​ (c) “Anthracene and phenanthrene are more reactive toward the electrophilic
substitution reaction than naphthalene and benzene”- How will you explain
the statement? 3
(d) “The electrophilic aromatic substitution reaction of anthracene and phenanthrene
are not synthetically important as those of naphthalene”- How will you explain the
tatement?
​(e) At what position does naphthalene undergo electrophilic substitution reaction? Give
explanation in favor of your answer.
3. (a) Draw the structure of anthracene and phenanthrene with the numbering of all
carbon atoms and answer the following questions: 2
(i) Are anthracene and phenanthrene bridge or fused ring polycyclic compounds? 1
(ii) Are anthracene and phenanthrene aromatic compounds? Give explanation
in support of your answer. 2
(iii) Draw the all possible resonance structures of anthracene and phenanthrene. 4
(iv) Are all the carbon-carbon bond lengths in anthracene and phenanthrene same? Give
reason in support of your answer. 3
(v) How can you chemically distinguish between anthracene and phenanthrene? Give
necessary chemical equitation. 2
(b) Give a method for the preparation of​ ​anthracene​. ​3

4. (a) Briefly discuss how the structure of naphthalene has been established by
degradative chemical method. 3
​(a) Number the all ring carbon atoms of the following two compounds (​I​ and ​II​)
and answer the following questions: 1
 2

(i) Why the resonance energy of phenanthrene is greater (92kcal/mol) than anthracene
(84 kcal/mol) although both of them have three fused benzene rings system? 2
(ii) Why the electrophilic aromatic substitution reaction of the above two compounds
(​I ​and ​II​) occurs in the middle ring B in the above two compounds instead of the rings
A and C? Give explanation in support of your answer. 2
(iii) Which of the compounds readily undergo reductive ozonolysis reaction? Give
reason in favor of your answer. 2
(iv) Which of the compounds will form adduct with maleic anhydride? Give
reason in favor of your answer.
(v) Write down the Haworth synthesis of the compound (​I​). 3
(b) How will you carry out the following conversions: 2×3=6