Alkyl Halides 145 Chem1

2 Alkyl Halides

145 Chem3 CH 3 -X and R-CH 2 -X : Primary alkyl halide. (R) 2 -CH-X : Secondary alkyl halide. (R) 3 -C-X : Tertiary alkyl halide. Classes and Names of Halogen Compounds According to hydrocarbon gp. 1-Alkyl halides( R-X) has a halogen atom bonded to one sp3 hybrid C atom 2-Allylic halides has a halogen atom bonded to one sp3 hybrid C atom 3-Vinylic halides has a halogen atom bonded to one sp2 hybrid C atom 4-Benzylic halides has a halogen atom bonded to Carbone one away from aromatic ring 5-Aryl halides has a halogen atom bonded directly to an aromatic ring Alkyl Halides

1-Alkyl halides ( R-X): CH 3 -ClCH 3 -CH 2 -Br(CH 3 ) 2 -CH-F CommonMethyl ChlorideEthyl bromideIsopropyl fluoride IUPACChloromethaneBromoethane2-Fluoropropane Class1° 2° Common Cyclohexyl Iodide t.Butyl bromideMethylcyclopentyl chloride IUPACIodocyclohexane 2-Bromo-2- methylpropane 1-Chloro-1- methylcyclopentane Class2°3° 145 Chem4 Alkyl Halides

145 Chem5 3-Allyl halides C=C-C- X CH 2 =CHCH 2 Cl Allyl chloride 3-Chloro-1-propene 3-Chlorocyclopentene 4-Benzylic halides:Ar-C-X Benzyl Chloride 2-Vinylic halides Bromocyclohexene C=C-X CH 2 =CHBr Vinyl bromide Bromoethene 5-Aryl halides: Ar-X (X directly attached to  ) Chlorobenzene p-Bromo toluene Notice Alkyl Halides

145 Chem6 PHYSICAL PROPERTIES OF ORGANIC HALIDES All organic halides are insoluble in water and soluble in common organic solvents. In an alkyl halide, the halogen is more electronegative that carbon The boiling points increases with increasing in molecular weights. Alkyl halides have higher melting point than the corresponding alkanes, alkenes, and alkynes because: 1. Polarity 2. Molecular weight (In series of halides BP. F <Cl <Br <I) Alkyl Halides

145 Chem7 PREPARATION OF HALOGEN COMPOUNDS 1- Direct halogenation of hydrocarbons a- Halogenation of alkanes b- Halogenation of alkenes Alkyl Halides CH 3 CH=CHCH 3 + H-Cl CH 3 CHHCHClCH 3 (one) CH 3 CH=CH 2 + Cl 2 CH 3 CHClCH 2 Cl CCl 4

145 Chem8 c- Halogenation of alkynes Alkyl Halides

d- Halogenation of alkyl benzenes and aromatic ring 145 Chem9 Alkyl Halides

145 Chem10 2- Conversion of alcohols Alkyl Halides

Reactions of Organic Halides 1- Nucleophilic Subtitution Reactions Nu - = - OH, - OR, - OCOR, - SH, - SR, - CN, 145 Chem11 Alkyl Halides

145 Chem12 Alkyl Halides

2- Elimination Reactions 145 Chem13 Alkyl Halides

3- Reaction of Grignared reagent a- Formation of Grignard reagent b- Reaction of Grignard reagent 145 Chem14 Alkyl Halides

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