Chapter 9: ALKYL HALIDES ppsx

1 ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 ext. 5681 Email: ptsnam@hcmut.edu.vn 2 Chapter 9: ALKYL HALIDES 3 NOMENCLATURE OF ALKYL HALIDES Common names: alkylhalide (chloride, bromide…) IUPAC names: halogeno + alkane (chloro, bromo…) 4 Alkyl & halogen substituents are considered of equal rank 5 PREPARATION OF ALKYL HALIDES Alkyl halides from alcohols Only in acidic conditions 6 Alkyl halides from alkenes More stable 7 Alkyl halides from alkanes Chlorination is much less selective 8 REACTIONS OF ALKYL HALIDES Very reactive Very unreactive With the same R 9 NUCLEOPHILIC SUBSTITUTION REACTIONS S N 1 & S N 2 – depending on alkyl structure, nucleophile concentration & reactivity, and solvent 10 Functional group interconversions of 1 o & 2 o alkyl halides Elimination reactions will occur for 3 o alkyl halides [...]...Elimination reactions will occur for 3o alkyl halides 11 Williamson ether synthesis 12 Nucleophilic substitutions Eliminations 13 ELIMINATION REACTIONS In an elimination reaction: + Groups / atoms are eliminated from a reactant + A double bond... indicate that the acid is not added until the reaction with the Grignard reagent is complete 23 Reactions of Grignard reagents with esters Can NOT be isolated 24 Can be chiral Alcohols from esters / acyl halides Can NOT be chiral 25 Reactions of Grignard reagents with nitriles 26 Reactions of Grignard reagents with carbon dioxide 27 Reactions of Grignard reagents with epoxides 28 . ptsnam@hcmut.edu.vn 2 Chapter 9: ALKYL HALIDES 3 NOMENCLATURE OF ALKYL HALIDES Common names: alkylhalide (chloride, bromide…) IUPAC names: halogeno + alkane (chloro, bromo…) 4 Alkyl & halogen. considered of equal rank 5 PREPARATION OF ALKYL HALIDES Alkyl halides from alcohols Only in acidic conditions 6 Alkyl halides from alkenes More stable 7 Alkyl halides from alkanes Chlorination is. interconversions of 1 o & 2 o alkyl halides Elimination reactions will occur for 3 o alkyl halides 11 Elimination reactions will occur for 3 o alkyl halides 12 Williamson ether synthesis