Cambridge International A Level Chemistry Answers to self-assessment questions

Answers to SAQs
Chapter 25 ii C6H4(NO2)CH3 + H2O
iii 1-methyl-2-nitrobenzene and
1 a 6 1-methyl-4-nitrobenzene
b p (or 2p) orbitals iv CH3 CH3

c electrons that are free to move around the NO2 O2N NO2
molecule in the π bonding system above and
below the plane of the carbon atoms in the
benzene ring NO2 NO2

d In benzene the six electrons in the π bonding 1-methyl-2,4-dinitrobenzene 1-methyl-2,4,6-trinitrobenzene

system are no longer associated with any b i sulfur atom

particular carbon atoms in the molecule, ii C6H6 + SO3 → C6H5SO3H
whereas in hex-3-ene the two electrons in the
π bond in the centre of the molecule are only 5 a i C6H5CH2CH2CH3 + HCl
found above or below the central two carbon ii C6H5COCH2CH2CH2CH3 + HCl
atoms. b i propylbenzene
2 a i Br
ii (aryl) ketone

6 With hexylbenzene, the hexyl side chain would

be oxidised to form an aryl carboxylic acid
Br Br
(and the purple potassium manganate(VII)
Cl
ii solution would be decolourised), whereas no
reaction would occur with hexane.
O2N Cl 7 a HCl, CH3COOH, C6H5OH, H2O, C3H7OH
b i 2-methylphenol b Methanol is less acidic than phenol because
ii 1-bromo-2,3-dichlorobenzene methanol has an electron-donating methyl
group attached to the oxygen atom in the
3 a Cl methoxide ion that is formed on dissociation.
This has the effect of concentrating more
FeCl3
+ Cl2 + HCl negative charge on this oxygen atom, which
more readily accepts an H+ ion, re-forming
b electrophilic substitution undissociated methanol. On the other hand,
c the phenoxide ion, C6H5O–(aq), has its negative
H Cl Cl
charge spread over the whole ion as the benzene
stage 1
Cl+ ⎯⎯⎯→ +
stage 2
⎯⎯⎯→ + HCl ring draws in electrons from the oxygen atom,
[FeCl4]– (+FeCl3) reducing the attraction of this ion for H+ ions.
CH3
d 8 a C6H5OH, C6H5CH3, C6H6, C6H5COOH
Br Br
(remember –COOH is a deactivating group)
b i OH OH
Cl Cl
Br
+ 3Cl2 + 3HCl
e The hydrogen atoms in the –CH3 side-chain
would be all or partially replaced by Br atoms. Cl
f free-radical substitution ii A catalyst of anhydrous FeCl3/Fe or AlCl3
4 a i C6H4(NO2)CH3 + H+ would be needed.

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