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When acetic acid is treated with isotopically labeled

Chapter 21, Problem 21.6

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QUESTION:

When acetic acid is treated with isotopically labeled water ( 18O, shown in red) in the presence of a catalytic amount of acid, it is observed that the isotopic label becomes incorporated at both possible positions of acetic acid. Draw a mechanism that accounts for this observation. OH O OH O OH O [H+] H2O +

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QUESTION:

When acetic acid is treated with isotopically labeled water ( 18O, shown in red) in the presence of a catalytic amount of acid, it is observed that the isotopic label becomes incorporated at both possible positions of acetic acid. Draw a mechanism that accounts for this observation. OH O OH O OH O [H+] H2O +

ANSWER:

Step 1 of 3

This exercise tells us that when acetic acid is treated with isotopically labeled water (18O, shown in red) in the presence of a catalytic amount of acid, it is observed that the isotopic label becomes incorporated at both possible positions of acetic acid.

We’re asked to draw a mechanism that accounts for this observation.

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