Aromatic Compunds- Benzenes And Phenol
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What are additional groups of a phenyl amine?
Amine group (NH2)
What are additional groups of nitrobenzene?
Nitrite (NO2)
What are additional groups of 2,4,6 trichlorophenol?
3 Cl, 1 OH
What are additional groups of 1,3,5 trinitrotoluene?
3 NO2 1 CH3
What are additional groups of 2-hydroxybenzoic acid?
OH COOH
How is the first piece of evidence against the kekulé model?
Benzene is less reactive than cyclohexene despite despite it having more double bonds and doesn’t undergo electrophilic addition
What is the second piece of evidence against the kekulé model?
Benzene is less exothermic in hydrogenation, and more stable than expected
What is the delocalisation energy?
The increase in stability connected to delocalised electrons
What is the third piece or evidence against the kekulé structure?
If benzene had alternating single and double bonds, it’s shape wouldn’t be a regular hexagon, as single bonds are longer than double bonds, and in benzene all bonds are the same length
What are arenes?
Arenes are aromatic hydrocarbons containing at least 1 benzene ring
What is the kekulé structure?
Benzene has alternating double and single bonds
What is the actual structure of benzene?
Each carbon atom is bonded to two other carbon atoms and one hydrogen atom 3 electrons are used, and the last unused electron is delocalised, and these form a ring shape above and below the plane of the benzene ring
What is the shape of each carbon atom in benzene?
Triganol planar Bond angle- 120°C
What is the overall equation of nitration?
Benzene + HNO3 —> Nitrobenzene + H2O
What are the reagents required for nitration, the mechanism and the electrophile?
Reagent- concentrated HNO3 and concentrated H2SO4 at 50°C Mechanism- electrophilic substition Electrophile- NO2+
What is the first stage of nitration?
Stage 1- formation of NO2+ HNO3 + H2SO4 —> HSO4- + H2NO3+ H2NO3+ —> NO2+ + H2O
What is the second stage of nitration?
2nd stage- the mechanism
What is the third stage of nitration?
3rd stage- regeneration of the catalyst HSO4- + H+ —> H2SO4
What is the equation for the halogenation of benzene?
Benzene + Cl2 —> Chlorobenzene + HCl
What is the electrophile, the mechanism and reagents required halogenation of benzene?
Mechanism- electrophilic substition Reagent (catalysts)- AlCl3 or FeCl2 Electrophile- CH3CH2C+H2
What is the equation for the regeneration of the catalyst in the halogenation of benzene?
H+ + AlCl4- —> AlCl3 + HCl
What is alkylation (Friedal-crafts)?
The reaction between benzene and haloalkanes
What is the overall question for the reaction between benzene and a haloalkane (e.g CH3CH2CH2Cl)?
Benzene + CH3CH2CH2Cl —> propylbenzene + HCl