[1] NaOH [2] H,O* HO, HO. HO,

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter2: Polar Covalent Bonds; Acids And Bases
Section2.SE: Something Extra
Problem 25MP: Use curved arrows to draw the protonated form of each Lewis base below.
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Explain the following result. Acetic acid (CH3COOH), labeled at its OH oxygen with theuncommon 18O isotope (shown in red), was treated with aqueous base, and then the solution was acidied. Two products having the 18O label at different locations were formed.

[1] NaOH
[2] H,O*
HO,
HO.
HO,
Transcribed Image Text:[1] NaOH [2] H,O* HO, HO. HO,
Expert Solution
Step 1

Acetic Acid (CH3COOH) when treated with NaOH (Strong Base) deprotonation reaction takes place and Carboxylate anion is formed.

Chemistry homework question answer, step 1, image 1

Step 2

Resonance will stabilize the Carboxylate anion.

Chemistry homework question answer, step 2, image 1

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