Preparation of Alkyl Halides Product Type of Reaction (name) Reaction Halides from alkenes Electrophilic Addition HX, organic solvent (anhydrous)
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[PDF] Chapter 6 – Reactions of Alkyl Halides
Both the alkyl halide and nucleophile are involved in the rate- limiting step (the reaction NaN3 N3 Cl NaN3 N3 Cl o Suitability of alkyl halides as substrates
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Substitution Reactions: two reactants exchange parts to give new products A-B + C-D allylic and benzylic alkyl halides can react by either SN1 or SN2 OH 2
[PDF] Preparation of Alkyl Halides Reactions of Alkyl Halides
Preparation of Alkyl Halides Product Type of Reaction (name) Reaction Halides from alkenes Electrophilic Addition HX, organic solvent (anhydrous)
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The rate of any SN2 reaction is directly linked to the concentration of two species, the Nucleophile (Nuc) and the alkyl halide (RX) undergoing substitution Both of
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The rate of an SN1 reaction is affected by the type of alkyl halide involved • This trend is exactly opposite to that observed in SN2 reactions Page 27 27
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The characteristic reactions of alkyl halides are nucleophilic substitution and benzyl halide react with both ethanol and ethoxide ion to form substitution
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Preparation of Alkyl Halides
ProductType of Reaction (name)Reaction ConditionsSelectivity (Regio- and/or Stereo-) Halides from alkenesElectrophilic AdditionHX, organic solvent (anhydrous)Markovnikov Addition from alkenesFree Radical Addition HBr, H2O2, hnAnti-Markovnikov from alkanesFree Radical SubstitutionX2, hnbenzylic > allylic > 3° > 2° > 1° from alkenesFree Radical SubstitutionNBS, hn (gives allylic bromides)benzylic and allylic H's from alcoholsSubstitutionHX, ether (anhydrous)3° alcohols only from alcoholsSubstitutionSOCl2 (gives alkyl chlorides)1° and 2° alcohols from alcoholsSubstitutionPBr3(gives alkyl bromides)1° and 2° alcohols_____________________________1,2-halides (vic-dihalide) Electrophilic AdditionCl2, Br2, I2in CCl4solventAnti Stereochemistry
from alkenes ____________________1,1,2,2-tetrahaloalkanes Electrophilic AdditionX2(excess), anhydrous from alkynes___________________1,1-dihaloalkane (gem-dihalide)Electrophilic AdditionHX (excess), anhydrousMarkovnikov
from alkynes______________________vinyl halide from alkynesElectrophilic AdditionHX (1 equivalent), anhydrous Markovnikov, trans-addition of H-X
______________________1,2-Dihaloalkene from alkynesElectrophilic AdditionX2(1 equivalent), anhydroustrans addition of X-X
______________________Reactions of Alkyl Halides Alkenesfrom alkyl halidesElimination of HXStrong Base (NaOH or NaNH2)____________________________Alkynesfrom 1,2-dihalidesDouble Elimination of HXNaNH2, NH3_________________________Grignard Reagents (R-MgX from R-X)1°, 2°, 3°-Alkyl, vinyl or aryl halide and Mg(0) in THF or ether
____________________________Organolithium (R-Li from R-X)1°, 2°, 3°-Alkyl, vinyl or aryl halide and Li(0)in pentane
____________________________Cuprate (Gilman's Reagent) (R2CuLi from R-Li)Organolithium + CuI in THF or ether
____________________________Organometallic CouplingSubstitutionCuprate + alkyl halide to give an alkane
Cuprate + vinyl halide to give a substituted alkene