ORGANIC CHEMISTRY (PETRO)

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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 Chapter 9: ALKYL HALIDES NOMENCLATURE OF ALKYL HALIDES Common names: alkylhalide (chloride, bromide…) IUPAC names: halogeno + alkane (chloro, bromo…) Alkyl & halogen substituents are considered of equal rank PREPARATION OF ALKYL HALIDES Alkyl halides from alcohols Only in acidic conditions Alkyl halides from alkenes More stable Alkyl halides from alkanes Chlorination is much less selective REACTIONS OF ALKYL HALIDES Very reactive Very unreactive With the same R NUCLEOPHILIC SUBSTITUTION REACTIONS SN1 & SN2 – depending on alkyl structure, nucleophile concentration & reactivity, and solvent Functional group interconversions of 1o & 2o alkyl halides Elimination reactions will occur for 3o alkyl halides 10 ELIMINATION REACTIONS In an elimination reaction: + Groups / atoms are eliminated from a reactant + A double bond is formed between the carbons from which atoms are eliminated 14 15 16 Zaitsev’s product Hofmann’s product 17 GRIGNARD REAGENTS Strong base Strong nucleophile 18 REACTIONS OF GRIGNARD REAGENTS Strong base Grignard reagents readily react with acidic groups: -OH, -NH2, -NHR, -SH, -C≡CH, -COOH19 Reactions of Grignard reagents with aldehydes & ketones Only for the reaction of HCHO 20 21 22 Numbers & are used to 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
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