Aromatic Hydrocarbons

EXERCISES
13.1 How do you account for the formation of ethane during chlorination of methane ?
13.2 Write IUPAC names of the following compounds :
(a) CH3CH=C(CH3)2 (b) CH2=CH-CC-CH3
(c) (d) –CH2–CH2–CH=CH2
(e)
3 24 23 3
2 32
(f ) CH (CH ) CH(CH ) CH
|
CH CH(CH )
(g) CH3 – CH = CH – CH2 – CH = CH – CH – CH2 – CH = CH2
|
C2H5
13.3 For the following compounds, write structural formulas and IUPAC names for all
possible isomers having the number of double or triple bond as indicated :
(a) C4H8 (one double bond) (b) C5H8 (one triple bond)
13.4 Write IUPAC names of the products obtained by the ozonolysis of the following
compounds :
(i) Pent-2-ene (ii) 3,4-Dimethyl-hept-3-ene
(iii) 2-Ethylbut-1-ene (iv) 1-Phenylbut-1-ene
13.5 An alkene ‘A’ on ozonolysis gives a mixture of ethanal and pentan-3-
one. Write structure and IUPAC name of ‘A’.
13.6 An alkene ‘A’ contains three C – C, eight C – H ó bonds and one C – C
ð bond. ‘A’ on ozonolysis gives two moles of an aldehyde of molar mass
44 u. Write IUPAC name of ‘A’.
13.7 Propanal and pentan-3-one are the ozonolysis products of an alkene?
What is the structural formula of the alkene?
13.8 Write chemical equations for combustion reaction of the following
hydrocarbons:
(i) Butane (ii) Pentene
(iii) Hexyne (iv) Toluene
13.9 Draw the cis and trans structures of hex-2-ene. Which isomer will have
higher b.p. and why?
13.10 Why is benzene extra ordinarily stable though it contains three double
bonds?
13.11 What are the necessary conditions for any system to be aromatic?
13.12 Explain why the following systems are not aromatic?
(i) (ii) (iii)
13.13 How will you convert benzene into
(i) p-nitrobromobenzene (ii) m- nitrochlorobenzene
(iii) p - nitrotoluene (iv) acetophenone?
13.14 In the alkane H3C – CH2 – C(CH3)2 – CH2 – CH(CH3)2, identify 1°,2°,3° carbon
atoms and give the number of H atoms bonded to each one of these.
13.15 What effect does branching of an alkane chain has on its boiling point?
13.16 Addition of HBr to propene yields 2-bromopropane, while in the presence
of benzoyl peroxide, the same reaction yields 1-bromopropane. Explain
and give mechanism.
13.17 Write down the products of ozonolysis of 1,2-dimethylbenzene (o-xylene).
How does the result support Kekulé structure for benzene?
13.18 Arrange benzene, n-hexane and ethyne in decreasing order of acidic
behaviour. Also give reason for this behaviour.
13.19 Why does benzene undergo electrophilic substitution reactions easily
and nucleophilic substitutions with difficulty?
13.20 How would you convert the following compounds into benzene?
(i) Ethyne (ii) Ethene (iii) Hexane
13.21 Write structures of all the alkenes which on hydrogenation give
2-methylbutane.
13.22 Arrange the following set of compounds in order of their decreasing
relative reactivity with an electrophile, E+
(a) Chlorobenzene, 2,4-dinitrochlorobenzene, p-nitrochlorobenzene
(b) Toluene, p-H3C – C6H4 – NO2, p-O2N – C6H4 – NO2.
13.23 Out of benzene, m–dinitrobenzene and toluene which will undergo
nitration most easily and why?
13.24 Suggest the name of a Lewis acid other than anhydrous aluminium
chloride which can be used during ethylation of benzene.
13.25 Why is Wurtz reaction not preferred for the preparation of alkanes
containing odd number of carbon atoms? Illustrate your answer by

taking one example.