ORGANOHALOGENS

Dr. K. Hylton October 2011

STRUCTURE
Refers to organic compounds in which halogen is directly bonded to C (C-X) E.g chloromethane (CH3Cl)

The halogen is named as a substituent Bond is polar due to high electronegativity (relative to C) May be 1, 2, or 3 Susceptible to nucleophilic substitution reactions

STRUCTURE
Draw the following: Chloroethane

1,1-dichloro-2,2-dibromobutane 2,2,3,4-tetraiodopentane

NUCLEOPHILIC SUBSTITUTION
SN1: Unimolecular Nucleophilic Substitution Two step reaction Intermediate: carbocation Preferred for tertiary alkylhalides Rate dependent only on [R-X] such that Rate = k[R-X]

NUCLEOPHILIC SUBSTITUTION
SN2: Bimolecular Nucleophilic Substitution Concerted mechanism (everything happens simultaneously) Intermediate: unstable pentacoordinate specie Prefered for primary alkyl halides Rate depends on both [R-X] and [Nu-] Rate =k [R-X] [Nu-]

NUCLEOPHILIC SUBSTITUTION
Nucleophilic Substitution reactions using : 1. Water alcohol

2. Cyanide

nitrile

3. Ammonia

amine

1, 2-ELIMINATION

Alkylhalides also undergo elimination reactions in which H and X are lost

E.g Dehydrobromination of 2-bromo-2methylpropane( in presence of polar solvent) alkene Mechanism includes: Ionization Removal of proton Formation of double bond

ENTHALPY LEVEL DIAGRAMS

EXOTHERMIC

ENTHALPY LEVEL DIAGRAMS

ENDOTHERMIC