1 CH
2 3
3 Atoms in the ring rather than being localised in three distinct double bonds.
4
1 Van der Waals forces
2
a 1,3-dichlorobenzene
b 1-bromo-4-chlorobenzen
3 a 1,4-dimethglbenzene
b 1,2-dimethylbenzene
4
R+
1
a A electrophilic substitution
b A electrophilic substitution
2 1,2-dinitrobenzene and 1,4-dinitrobenzene
3
Addition reactions would involve the loss of aromatic stability.
4
Banner 2conc HNO3
conc H2SO4
HNO3 + 2H2SO4 → NO2+ + H3O+ + 2HSO4–
2
CH3COCl + AlCl3 → CH3+CO + AlCl4–
Electrophilic substitution
3
CH3COCl + AlCl3 → CH3+CO + AlCl4–
Electrophilic substitution
4
(a) CH3CO+
(b)
5
(a)
CH3CH2COCl OR CH3CH2CClO OR propanoyl chloride
OR (CH3CH2CO)2O OR propanoic anhydride
Penalize contradiction in formula and name, e.g., propyl chloride
AlCl3 or FeCl3 or names
CH3CH2COCl + AlCl3 → CH3 CH2CO+ + AlCl4–
Allow RCOCl in equation but penalise above
(b)
(c)
Tollens or ammoniacal silver nitrate
6 (a)
(
Benzene is more stable than cyclohexatriene
Because of delocalisation or electrons spread out or resonance
B
conc HNO3
conc H2SO4
2 H2SO4 + HNO3 → 2HSO4– + NO2+ + H3O+
7
[CH3CH2CO]+
CH3CH2COCl + AlCl3 → [CH3CH2CO]+ + AlCl4_
8
(4 marks) AQA. 2004
Cyclohexane evolves 120 kJ mol-1
Therefore expect triene to evolve
360 kJ mol-1;
or 3 × 120 = 360 kJ mol-1
360 – 208 = 152 kJ;
Benzene lower in energy / more stable; due to delocalisation;
9
(a)
Nitric acid and sulfuric acid
(b) Explosives / dyes / fibres / pharmaceuticals
(c) (i)
C6H6 + HNO3 → C6H5NO2 + H2)
(ii) It accepts a pair of electrons
(iii)
Electrophilic substitution.
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