Organic halides Dr. Nabila A.Aziz Al-Jaber Associate Professor of Chemistry Chemistry Department Faculty of Sciences King Saud University. Dr. Nabila A.Aziz.

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Organic halides Dr. Nabila A.Aziz Al-Jaber Associate Professor of Chemistry Chemistry Department Faculty of Sciences King Saud University. Dr. Nabila A.Aziz Al-Jaber Associate Professor of Chemistry Chemistry Department Faculty of Sciences King Saud University.

Organic Halides Source &important: 1-Rare in nature produced by micro. Algi. (Ab. Th.) 2-used (herbicides, detergent, insecticide) 3-intermediat for synthesis. Classes & Names: According to hydrocarbon gp. 1-Alkyl halides( R-X): 2-Allyl halides 3-Vinyl halides 4-Benzyl halides 5-Aryl halides

1-Alkyl halides( R-X): CH 3 Cl CH 3 CH 2 CH 2 Br CH 3 CHFCH 3 Comm.: Methyl Chloride n- propyl bromide isopropyl fluoride IUPAC: Chloromethane 1-Bromo propane 2-fluoropropane Class 1  1  2  Co. Cyclo hexyl iodide Methyl cyclopentyl chloride t-Butyl romide IUPAC idocyclohexane 1-Chloro-1-methylcyclopentane 2-bromo2-methylpropane Class: 2  3  3 

2-Allylic halides C=C-C- X CH 2 =CHCH 2 Br CH 3 CH=CHCH 2 Cl Comm. Allyl bromide Allyl chloride IUPAC 3-Bromo-1-propene 1-Chloro-2-butene 3-Chlorocyclopentene 3-Bromocyclohexene 4-Benzylic halides: Ar-C-X ( halogen one carbon away from aromatic ring) Benzyl Chloride Diphenyl methylbromide

5-Aryl halides: Ar-X (X directly attached to  ) Chlorobenzene p-Bromo toluene Physical Properties: sol. In organic solvent (in sol. In H 2 O) BP.  with  Mwt.( Straight chain  branched) In series of halides Bp. F <Cl <Br <I

Preparation Of Halogen compounds 1]Direct Halogenation of hydrocarbons a) Halogenation of alkanes(alkyl halides ) eg, b)Halogenation of alkenes (allyl halides) c)Halogenation of benzene(benzyl halides)

Preparation Of Halogen compounds c)Halogenation of benzene(benzyl halides)

d) Halogenation of aromatic ring (aryl halides) 2]Addition of HX to unsaturated hydrocarbons a)To alkenes (alkyl halides) 3 eg. b)To alkynes (Vinyl halides) 3

3] Conversion of alcohol (alkyl halides) 1  &2  need catalyst, 3  without catalyst

Reactions of organic halides 1] Nucleophilic substitution reaction ( S N 1, S N 2) a) RX+ NaOH / H 2 O(or(KOH/H 2 O) ROH (alc.) b) RX+KCN / NaCN R-CN (nitrile)

c) RX+ NaOR / alcohol( or KOR) ROR (ether) d) RX + R/-C≡C-Na(* liq.NH 3 ) R/-C≡C-R (alky.) e) RX + R'NH 2 /liq.NH 3 RNHR' (amine) g) RX + NaI R-I

2]Elimination reactions 3]Reaction of Gregnared reagent R-X +Mg R-X -Mg Ar-X +Mg Ar-X –Mg 4]Reduction of alkyl halides(by metal and acid) 3 3