8.39The substrate is a tertiary alkyl bromide and can undergo SN1 substitution and E1 elimination underthese reaction conditions. Elimination in either of two directions to give regioisomeric alkenes canalso occur.8.40Solvolysis of 1,2-dimethylpropyl p-toluenesulfonate in acetic acid is expected to give one substitu-tion product and two alkenes.Since fve products are formed, we are led to consider the possibility of carbocation rearrangementsin SN1 and E1 solvolysis.Since 2-methyl-2-butene is a product common to both carbocation intermediates, a total of fve dif-ferent products are accounted for. There are two substitution products:and three elimination products:8.41Solution A contains both acetate ion and methanol as nucleophiles. Acetate is more nucleophilicthan methanol, and so the major observed reaction is:MethyliodideCH3I1AcetateCH3CO2OMethyl acetateCH3OCCH3Omethanol2-Methyl-2-buteneCHCH3(CH3)2C3-Methyl-1-butene
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This note was uploaded on 09/26/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.