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1. Alkanes
a. Reactions
Combustion
Free-radical substitution
o Steps
Initiation
Propagation
Termination
o Conditions
Cl2(g)/Br2(l), UV light
b. Formation
Dehydration of Alcohols
o Excess, concentrated H2SO4, 180oC
o Al2O3, 400oC
Dehydrohalogenation of halogenoalkane
o Alcoholic KOH, relfux
2. Benzene
a. Reactions
Nitration
o Concentrated HNO3, concentrated H2SO4, reflux at less
than 60oC
Halogenation
o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature
Friedel-Crafts Alkylation
o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature
Friedel-Crafts Acylation
o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature
3. Alkylbenzene
a. Reactions (side-chain)
Halogenation
o Cl2(g)/Br2(l), UV light
Oxidation
o Alkaline/ acidified KMnO4, reflux
o Entire side chain is oxidized into CO 2H
b. Formation
Friedel-Crafts Alkylation
o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature
4. Alcohols
a. Reactions
Esterification
o Concentrated H2SO4, reflux
Acylation
Halogenation (hydrogen halide)
o NaCl(s), concentrated H2SO4, reflux
o HX, reflux
Halogenation (phosphorus halide)
o Cold PCl5
o Red P and Br2, reflux
o Red P and I2, reflux
Done by Nickolas Teo Jia Ming, CG 12/11
Halogenation (Sulfur dichloride oxide)
o SOCl2, dissolved in pyridine
Dehydration
o Excess, concentrated H2SO4, 180oC
o Al2O3, 400oC
Formation of alkyl hydrogensulfate
o Concentrated H2SO4, reflux at 80oC
Combustion
Oxidation
o For aldehyde
Acidified K2Cr2O7, heat to distill
o For carboxylic acid/ ketone
Acidified K2Cr2O7/ KMnO4, reflux
b. Formation
Alkaline hydrolysis of halogenoalkane
o Aqueous KOH, reflux
Direct hydration of alkenes
o Steam, H3PO4 catalyst, 300oC, 65 atm
Indirect hydration of alkenes
o Cold concentrated H2SO4, followed by heating in the
presence of water
Reduction of carbonyl compounds
o H2(g) with Ni catalyst at 140oC
o LiAlH4, dissolved in dry ether at room temperature
c. Test
Tri-iodomethane/ Iodoform test
o Alkaline I2(aq), heat
o Solid I2, NaOH(aq), heat
o NaOI(l), heat
5. Phenol
a. Reactions
Esterification
o Acid chloride and NaOH(aq)
Halogenation
o Br2 dissolved in CCl4
o Chlorine/ Bromine water at room temperature
Nitration
o Dilute HNO3, room temperature
b. Test
Neutral Iron(III) chloride solution at room temperature
o Violet coloration
Bromine water at room temperature
o Decolourisation and white precipitate
6. Aliphatic carbonyl compounds
a. Reactions
Oxidation of aldehydes
o Acidified K2Cr2O7/ KMnO4, heat
o Alkaline KMnO4, heat
o Tollens Reagent, heat
Ammoniacal silver(I) nitrate
o Fehlings Solution, heat