When acetone is dissolved in either a slightly basic or a slightly acidic solution of oxygen-18 labeled water, H2180, oxygen-18 labeled acetone, (CH3)2C=180, is produced. This is a form of an isotopic exchange reaction between acetone and water. Provide a mechanism to account for this reaction in (a) basic solution and (b) acidic solution. Hint: Is the addition of the nucleophile reversible or irreversible? 180 + H,180 CH3 + Hо `CH3 Acid or base H3C H3C

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When acetone is dissolved in either a slightly
basic or a slightly acidic solution of oxygen-18
labeled water, H2180, oxygen-18 labeled acetone,
(CH3)2C=180, is produced. This is a form of an
isotopic exchange reaction between acetone and water. Provide a mechanism to account for this reaction in (a) basic
solution and (b) acidic solution. Hint: Is the addition of the nucleophile reversible or irreversible?
180
+ H,180
CH3
+ Hо
`CH3
Acid or base
H3C
H3C
Transcribed Image Text:When acetone is dissolved in either a slightly basic or a slightly acidic solution of oxygen-18 labeled water, H2180, oxygen-18 labeled acetone, (CH3)2C=180, is produced. This is a form of an isotopic exchange reaction between acetone and water. Provide a mechanism to account for this reaction in (a) basic solution and (b) acidic solution. Hint: Is the addition of the nucleophile reversible or irreversible? 180 + H,180 CH3 + Hо `CH3 Acid or base H3C H3C
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