Reactions of alkanes, alkenes, alkynes and aromatics

alkane + halogen  haloalkane +hydrogen halide ALKANES Complete Combustion (Extreme Oxidation) Alkane + O2  CO2 + H2O Incomplete combustion Alkane + O2  CO + H2 O Substitution (with halides) alkane + halogen  haloalkane +hydrogen halide CH4 + Cl2 CH3Cl + HCl CH3Cl + Cl2  CH2Cl2 + HCl

ALKENES 1. Addition Reactions (breaking of the double bond) A) Halogenation (adding halides) alkene + halogen haloalkane B) Hydrogenation (adding hydrogen) alkene + hydrogen alkane CH2=CH2 + H2 CH3CH3

C) Hydrohalogenation (adding hydrogen halides) alkene + hydrogen halide haloalkane D) Hydration (adding water) alkene + water alcohol Hydrohalogenation and hydration follow Markovnikov’s Rule which states that the hydrogen is added to the carbon with the most hydrogen atoms originally bonded to it.

Markovnikov’s Rule When a hydrogen halide or water is added to an alkene or an alkyne, the hydrogen atoms bonds to the carbon atom of the multiple bond that already has more hydrogen atoms (“the rich get richer”) Propene reacts with hydrogen bromide 2-methyl-1-pentene reacts with water

ALKYNES 1. Addition Reactions (breaking of the multiple bond) A) Halogenation (adding halides) alkyne + 2 halogens haloalkane alkyne + 1 halogen haloalkene

B) Hydrogenation (adding hydrogen) alkyne + 2 hydrogen alkane

C) Hydrohalogenation (adding hydrogen halides) alkyne + 2 hydrogen halides haloalkane

Reactions of Aromatics 1. Substitution A) With Halogens benzene + halogen halobenzene + hydrogen halide

3. With Nitric Acid ( not mentioned in textbook) With Alkyl Halides benzene + alkyl halide alkyl benzene + hydrogen halide 3. With Nitric Acid ( not mentioned in textbook) benzene + nitric acid nitrobenzene + water