ARENES
- Created by: Katie
- Created on: 15-03-13 10:25
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- ARENES
- Benzene
- Structure
- Kekule suggested that benzene was a cyclic structure with alternating single and double bonds. BUT!!
- 1.It did not readily go under electrophilic addition
- 2. C-C bonds in benzene are an intermediate length between long C-C single bonds and short C=C bonds
- 3.Enthalphy of hydrogenation was less exothermic than expected
- Delocalised system
- Each Carbon has 4 electrons in its outer shell, 3are used to form sigma bonds. The 4th isinth sin the 2p orbital.
- The p orbital overlaps sideways with the neighbouring 2p orbitals, creating a ring of delocalised electrons above and below the carbon ring, creating a system ofpi bonds spread over all 6 carbons
- Each Carbon has 4 electrons in its outer shell, 3are used to form sigma bonds. The 4th isinth sin the 2p orbital.
- Kekule suggested that benzene was a cyclic structure with alternating single and double bonds. BUT!!
- Properties
- colourless at RTP
- Carcinogen
- Reactions
- Nitration C6H6+HNO3 --> C6H5NO2+ H2O Conc nitric acid, Conc sulphuric acid, reflux at 55oC
- Reduction of nitrobenzene C6H5NO2 +6[H] ----> C6H5NH2 +2H2O Tin and Conc sulphuric acid Reflux
- Diaziation of phenylamine C6H5NH2+ HNO2+HCl -----> C6H5N2Cl + 2H2O Nirtous acid and HCl below 10oC
- Substitution C6H5N2Cl +H2O ---> C6H5OH +N2+Cl. Above 10oC
- Phenol
- Properties
- Colourless, Cyrystaline
- Uses
- Use in plastics, antiseptics, disinfectants, resins
- Reactions
- Acts as a weak acid , releases the H+ from the OH group
- Reacts with NAOH to form a salt and Water
- Reacts with NA(s) to form an ionic salt and Hydrogen
- With Bromine without a catalyst, multi-substitution. Orange solution--> white ppt
- Properties
- Phenol
- Coupling C6H5N2Cl + C6H5OH +NaOH -->C6H5-N=NC6H4)H +NaCl +HCl Alkaline solutin below 10oC
- Substitution C6H5N2Cl +H2O ---> C6H5OH +N2+Cl. Above 10oC
- Diaziation of phenylamine C6H5NH2+ HNO2+HCl -----> C6H5N2Cl + 2H2O Nirtous acid and HCl below 10oC
- Reduction of nitrobenzene C6H5NO2 +6[H] ----> C6H5NH2 +2H2O Tin and Conc sulphuric acid Reflux
- Nitration C6H6+HNO3 --> C6H5NO2+ H2O Conc nitric acid, Conc sulphuric acid, reflux at 55oC
- Structure
- Phenol
- Properties
- Colourless, Cyrystaline
- Uses
- Use in plastics, antiseptics, disinfectants, resins
- Reactions
- Acts as a weak acid , releases the H+ from the OH group
- Reacts with NAOH to form a salt and Water
- Reacts with NA(s) to form an ionic salt and Hydrogen
- With Bromine without a catalyst, multi-substitution. Orange solution--> white ppt
- Properties
- Benzene
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