SUMMARY OF ORGANIC REACTIONS FOR ALKANES,

ALKENES, ALKYNES, AND BENZENE

(2nd Shifting Organic Chemistry)

Reaction Format:
General Reaction Mechanism:
1.) Reaction [reagent, catalyst] (product)
2.) Reaction [reagent, catalyst] (product)
3.) Reaction [reagent, catalyst] (product)

ALKANES
General Reaction Mechanism: FREE RADICAL SUBSTITUTION or SR
1.) Free radical substitution with halogens [X2, UV] (alkyl halide)

ALKENES
General Reaction Mechanism: ELECTROPHILIC ADDITION or AE
1.) Catalytic/Reductive Hydrogenation [H2, Pd/Pt/Ni] (alkane)
2.) Hydrohalogenation [HX, ether] (alkyl halide)
3.) Halogenation [X2, DCM] (vicinal dihalide)
4.) Acid-catalyzed Hydration [H2O, H3O+, H+, H2SO4] (alcohol)
5.) Epoxidation [peroxy acid (RCOOOH)] (epoxide/epoxide ring formation)
6.) Epoxide hydration [H2O] (vicinal diol)
7.) Mild oxidation [KMnO4, OH-] (vicinal diol)

ALKYNES
General Reaction Mechanism: ELECTROPHILIC ADDITION or AE
1.) Catalytic/Reductive Hydrogenation to produce alkene [H2, Lindlar's catalyst]
2.) Catalytic/Reductive Hydrogenation to produce alkane [2 H2, PtO2 or Pd/Pt/Ni]
3.) Hydrohalogenation [1 mole HX produces alkene halide, 2 moles HX produces gem dihalide]
4.) Halogenation [1 mole X2 produces vicinal dihalide, 2 moles X2 produces 1,1,2,2-tetrahalide]
5.) Hydration [H2O, H3O+, H+, H2SO4] (enol, which tautomerizes to keto form)
6.) Strong oxidation [KMnO4, H+] (if 3 oxidizable sites, half is carboxylic acid, if 4 = CO2)
7.) Acetylide ion formation [NaNH2 (sodium amide)] (acetylide ion)

BENZENE AND ITS DERIVATIVES

General Reaction Mechanism: ELECTROPHILIC SUBSTITUTION or SE
1.) Bromination [Br2, FeBr3/AlBr3] (Bromobenzene)
2.) Chlorination [Cl2, FeBr3/AlBr3] (Chlorobenzene)
3.) Sulfonation [concentrated H2SO4, fuming H2SO4] (Benzenesulfonate)
4.) Nitration [concentrated HNO3, concentrated H2SO4] (Nitrobenzene)
5.) Complete reduction of Benzene [3H2, Pd/Pt/Ni] (Cyclohexane)
6.) Friedel-Crafts Alkylation [RX, AlCl3] (Alkylbenzene)
7.) Friedel-Crafts Acylation [RCOX, AlCl3] (Acylbenzene)