Organic Reactions
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Alkane to Halogenoalkane CH3 CH 3 → CH3 CH2 Cl
Limited Cl2 , UV light Free Radical Substitution
Alkene to Alkane 2HC=CH2 → CH3-CH3 double open open up to add 2 H atoms
H2 (g), Ni, heat Addition of hydrogen, Reduction
Alkene to dihalogenoalkane 2HC=CH2 → CH2Br-CH2Br double open open up to add 2 Br atoms
Br 2 in CCl4 , dark and room temp Electrophilic Addition (Orange-red Br 2 in CCl 4 turns colourless) CCl4 solvent
Alkene to halogenoalcohol 2HC=CH2 → CH2Br-CH2OH
Br2 (aq), dark and room temp Electrophilic Addition (Orange Br2 (aq) turns colourless)
Alkene to halogenoalkane 2HC=CH2 → CH2H-CH2Br
HBr(g), room temp Electrophilic Addition
Alkene to alcohol 2HC=CH2 → CH2H-CH2OH
Conc. H2SO4 , cold (ii) H2O(l), heat Electrophilic Addition OR H2O (steam), H3PO4 catalyst, high temp high pressure Lab Method or Industrial Method
Alkene to carboxylic acid 2HC=CH2 → CH2H-COOH double bond cleaved to give carboxylic acid
KMnO4 (aq), H2 SO4 (aq), heat Oxidation (purple KMnO 4 turns colourless)
Alkene to diol 2HC=CH2 → CH2OH-CH2OH
KMnO4 (aq), H2SO4(aq), COLD Oxidation (purple KMnO 4 turns colourless)
Benzene to Cyclohexane Benzene ring into cyclic ring
H2 (g), Ni, high temp and high pressure Addition of hydrogen, Reduction
Benzene to chlorobenzene addition of Cl to benzene ring
Cl2 , anhydrous AlCl3 , room temp Electrophilic substitution AlCl3 is lewis acid catalyst
Benzene to nitrobenzene addition of NO2 to benzene ring
conc HNO3 , conc H2SO4 , heat in water bath at 60degrees Electrophilic substitution
Benzene to methylbenzene addition of CH3 to benzene ring STEP UP REACTION
CH3Cl, anhydrous AlCl3 , room temp Electrophilic substitution
Benzene to phenylethanone addition of COCH3 to benzene ring STEP UP REACTION
CH3 COCl, anhydrous AlCl3 , room temp Electrophilic substitution (White fumes of HCl)
benzene to benzoic acid oxidation of R group on benzene ring
KMnO4 (aq), H2 SO4 (aq), heat Side-chain Oxidation (purple KMnO 4 turns colourless, white ppt)
Methylbenzene to chloromethylbenzene substitution of Cl in CH3 of benzene ring
Limited Cl2 , UV light / high temperature Free Radical Substitution
Halogenoalkane to Alcohol CH3-CH2Br → CH3CH2OH Don’t forget!!!
NaOH(aq) or KOH(aq), heat Nucleophilic Substitution OH is the nucleophile
nitrobenzene to phenylamine replace NO2 with NH2 on benzene ring IMPTT
• Sn(s), conc HCl, heat 2.NaOH(aq), room temp Reduction
Halogenoalkane to Ether CH3-CH2Br → CH3CH2OCH3 STEP UP REACTION (TAKE NOTE!!!!!!) ether is R-O-R’
NaOCH3 in methanol, room temp Nucleophilic Substitution OCH3 is the nucleophile!!! methanol is solvant!
Halogenoalkane to Alkene CH2H-CH2Br → CH2=CH2 IMPTTT
NaOH(aq) or KOH(aq) in ethanol, heat Elimination
Halogenoalkane to Nitrile CH3-CH2Br → CH3CH2CN IMPTTT STEP UP REACTION
NaCN in ethanol, heat Nucleophilic Substitution
Halogenoalkane to amine CH3-CH2Br → CH3CH2NH2
Excess NH3 in ethanol, heat in sealed tube Nucleophilic Substitution (for polyalkylation use R-Br excess and conc NH3) polyalkylation product: N(CH3CH2)3
1° Alcohol to Aldehyde CH3-CH2OH → CH3-COOH
K2Cr2O7(aq), H2SO4(aq), heat with immediate distillation Oxidation Orange K2Cr2O7 turns green Cannot use KMnO 4 as aldehyde will oxidise to carboxylic acid
Alcohol to Halogenoalkane CH3-CH2OH → CH3-CH2Cl
• Anhydrous PCl5 (s), room temp (produces POCL3 + HCl white fumes) • Anhydrous PCl3 (l), room temp (produces H3PO3) • Anhydrous SOCl2 (l), room temp (produces SO2 + HCl white fumes) ALL ARE NUCLEOPHILIC SUBSTITUTIONS REACTIONS!!!! take note of liquid state for PCl3 and SOCl2!! ALL ROOM TEMP
Alcohol to Halogenoalkane CH3-CH2OH → CH3-CH2Cl PX3 (where X is CL or Br)
Anhydrous PCl3(l), room temp Nucleophilic Substitution (produce H3PO3)