Question

Mechanism. (Similar to Smith, 20.72) The existence of a tetrahedral intermediate in nucleophilic acyl substitution is supported by a series of experiments carried out by Myron Bender in 1951. In the key experiment, Bender carried out the following base catalyzed hydrolysis of ethyl benzoate, where the carbonyl oxygen was labeled with "0. Bender recovered some starting material from this reaction mixture where the carbonyl oxygen was no longer labeled. Propose a mechanism that explains this observation. Do we on Mechanism (Review). (Smith 10.58) Draw a mechanism that accounts for all three products shown

Answer 1

Catalyaolys of e benzoatt NaoH This is akus ploe due to duerearc of coneuntaiTo N| of reaetant. cRich is sRoun below -OH o H f eonewtrabron of reactont duereake, HRen backwond reocon takus loeu, Ren by backaond Yeochron, furten eyl benzoate Jormaron laku pbe Hao Heru 01 oxygen remain bam posikon Hasoy OH Prcbot muiteyk Hao igraron OH Bonding Profduct H OH H20, Profuct 3