Organic Chem Reactions
1. Alkanes
a. Reactions Combustion Free-radical substitution o Steps Initiation Propagation Termination o Conditions Cl2(g)/Br2(l), UV light b. Formation Hydrogenation of Alkeneso H2(g) with Nickel catalyst, at ~150oC, ~5atm
o H2(g) with Pt or Pd catalyst, at room temperature
Decarboxylation of sodium salt of carboxylic acid o Heating with sodalime
2. Alkenes
a. Reactions
Addition of bromine
o Br2(l) / Br2 dissolved in CCl4, room temperature
Addition of bromine water
o Bromine water at room temperature Addition of HBr
o HBr(g)/ HBr dissolved in CCl4, room temperature
Direct hydration
o Steam, H3PO4 catalyst, 300oC, 65 atm
Indirect hydration
o Cold concentrated H2SO4, followed by heating in the presence of
water
Addition of Hydrogen
o H2(g) with Nickel catalyst, at ~150oC, ~5atm
o H2(g) with Pt or Pd catalyst, at room temperature
Oxidation
o Partial bond cleavage
Cold alkali/ cold, dilute acidified KMnO4
o Total bond cleavage
Hot, acidified KMnO4
Combustion b. Formation Dehydration of Alcohols o Excess, concentrated H2SO4, 180oC o Al2O3, 400oC Dehydrohalogenation of halogenoalkane
o Alcoholic KOH, relfux
3. 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
4. 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 CO2H
b. Formation
Friedel-Crafts Alkylation
o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature
5. 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
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
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
6. 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
7. Aliphatic carbonyl compounds
a. Reactions
Oxidation of aldehydes
o Acidified K2Cr2O7/ KMnO4, heat
o Alkaline KMnO4, heat
o Tollen’s Reagent, heat
Ammoniacal silver(I) nitrate o Fehling’s Solution, heat
Alkaline copper(II) tartrate Reduction
o H2(g) with Ni catalyst at 140oC
o LiAlH4, dissolved in dry ether at room temperature
Addition of HCN
o HCN (aq), small amount of KCN, 10-20o
C Condensation reaction with Brady’s Reagent
o Brady’s Reagent, room temperature. b. Test
Tri-iodomethane test o Alkaline I2(aq), heat
o Solid I2, NaOH(aq), heat
o NaOI(l), heat c. Formation
Oxidation of alcohols
o Acidified K2Cr2O7/ KMnO4, heat (to distill for aldehyde)
8. Aromatic carbonyl compounds
a. Reactions
Oxidation of aldehydes o Acidified KMnO4, heat
o Alkaline KMnO4, heat
o Tollen’s Reagent, heat
Ammoniacal silver(I) nitrate o NOT Fehling’s solution
Reduction
o LiAlH4, dissolved in dry ether at room temperature
Condensation reaction with Brady’s Reagent o Brady’s Reagent, room temperature. Electrophilic substitution of benzene ring
o Fuming HNO, concentrated H2SO4, reflux at 40oC
o Cl2 , anhydrous FeCl3, at room temperature
b. Test
Tri-iodomethane test o Alkaline I2(aq), heat
o Solid I2, NaOH(aq), heat
o NaOI(l), heat c. Formation
For benzaldehyde
o Excess Cl2 gas and UV light, followed by reflux with NaOH (aq)
For phenylethanone
o CH3COCl with anhydrous AlCl3 catalyst, 40oC
9. Carboxylic acid
a. Reactions
Metal, metal carbonate, alkali o Room temperature
Formation of acyl chloride by a halogen atom o PCl5(s), cold
o PCl3(l), cold
o SOCl2, dissolved in pyridine
o Concentrated H2SO4, reflux
Reductions
o LiAlH4, dry ether, room temperature
b. Formation
Oxidation of primary alcohol
o Acidified K2Cr2O7/ KMnO4, reflux
Oxidation of aldehydes
o Acidified K2Cr2O7/ KMnO4, reflux
Oxidation of methyl benzene o Acidified KMnO4, heat
o Alkaline KMnO4, heat
Acid hydrolysis of nitriles o Dilute HCl, reflux Alkali hydrolysis of nitriles
o Dilute NaOH, reflux, followed by acidify
10. Carboxylic acid derivatives
a. Reactions
Hydrolysis o Ester
Dilute H2SO4, reflux
o Acyl chloride
Water, room temperature o Amide
Dilute HCl, reflux React with alcohol/ phenol
o Acyl chloride Room temperature Reaction with NH3 o Ester Concentrated alcoholic NH3 o Acyl chloride Room temperature Reduction o Ester
LiAlH4, dissolved in dry ether at room temperature
o Acyl chloride
LiAlH4, dissolved in dry ether at room temperature
o Amide
LiAlH4, dissolved in dry ether at room temperature
b. Formation
Acyl chloride
o Formation of acyl chloride by a halogen atom Ester
Amide
o Acyl chloride, NH3/ RNH2/ R2’NH, cold
11. Amine
a. Reactions
Alkylation of amine
o RX dissolved in ethanol in a sealed tube; Heat Acylation of amine
o Acyl chloride; Cold b. Formation
Reduction of nitriles
o LiAlH4, dry ether, room temperature
o H2(g) with Ni catalyst at 140oC
o Na and ethanol Reduction of amides
o LiAlH4, dry ether, room temperature
o H2(g) with Ni catalyst at 140oC
o Na and ethanol
12. Phenylamine
a. Reactions
Alkylation of amine
o RX dissolved in ethanol in a sealed tube; Heat Acylation of amine
o Acyl chloride; Cold Halogenation
o Br2 dissolved in CCl4
o Chlorine/ Bromine water at room temperature b. Formation
Reduction of nitrobenzene
o Sn, concentrated HCl, reflux followed by addition of NaOH (aq)
13.
Halogenoalkane
a. Reactions
Nucleophilic substitution o Alkaline hydrolysis
NaOH (aq); Reflux KOH (aq); Reflux o Formation of Nitrile
Alcoholic KCN; Reflux o Formation of ether
Na in excess alcohol; Reflux o Formation of ester
Silver(I) salt of carboxylic acid in alcohol; Reflux o Formation of amine
Excess concentrated NH3 in alcohol; Reflux
Elimination
Alcoholic KOH; Reflux Alcoholic CH3O-Na+; Reflux
b. Formation
Free radical substitution of alkane Halogenation of alcohols