A chemist proposes that the following reaction occurs via an SN2 mechanism rather than the usual addition-elimination reaction (i.e., addition of HO¯ at the carbonyl carbon followed by loss of methanol with reformation of the carbonyl) usually observed in ester hydrolysis reactions under basic conditions. On carrying out the reaction using 18O-labeled hydroxide anion in 180-labeled water (18OH /H21®O), the chemist finds that only 180-labeled methanol is produced. What does this suggest about the hypothesis? Explain. H,0 + H;C-ğH

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A chemist proposes that the following reaction occurs via an Sn2 mechanism rather than the
usual addition-elimination reaction (i.e., addition of HO at the carbonyl carbon followed by loss of
methanol with reformation of the carbonyl) usually observed in ester hydrolysis reactions under basic
conditions. On carrying out the reaction using 1$0-labeled hydroxide anion in 180-labeled water (1$OH
/H21$O), the chemist finds that only 180-labeled methanol is produced. What does this suggest about the
hypothesis? Explain.
HO:
H,0
Transcribed Image Text:A chemist proposes that the following reaction occurs via an Sn2 mechanism rather than the usual addition-elimination reaction (i.e., addition of HO at the carbonyl carbon followed by loss of methanol with reformation of the carbonyl) usually observed in ester hydrolysis reactions under basic conditions. On carrying out the reaction using 1$0-labeled hydroxide anion in 180-labeled water (1$OH /H21$O), the chemist finds that only 180-labeled methanol is produced. What does this suggest about the hypothesis? Explain. HO: H,0
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