On heating with aqueous acid, 2,2-dimethyl-2,3-butanediol (pinacol) rearranges to 3,3-dimethyl-2-butanone (pinacolone): HO OH H₂C-C-C-CH3 CH3 H₂O* C-C-CH3 + H₂O H3C CH3 H₂C CH3 pinacol pinacolone Draw structural formulas for the two carbocation intermediates in this reaction. . You do not have to consider stereochemistry. Do not include counter-ions, e.g., Na+, I, in your answer. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures using the sign from the drop-down menu.

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter19: Carboxylic Anhydrides, Esters, And Amides
Section: Chapter Questions
Problem 19.46P
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On heating with aqueous acid, 2,2-dimethyl-2,3-butanediol (pinacol) rearranges to 3,3-dimethyl-2-butanone (pinacolone):
HO
OH
H₂C-C-C-CH3
CH3
H₂O*
C-C-CH3
+ H₂O
H3C
CH3
H₂C
CH3
pinacol
pinacolone
Draw structural formulas for the two carbocation intermediates in this reaction.
.
You do not have to consider stereochemistry.
Do not include counter-ions, e.g., Na+, I, in your answer.
Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
Separate structures using the sign from the drop-down menu.
Transcribed Image Text:On heating with aqueous acid, 2,2-dimethyl-2,3-butanediol (pinacol) rearranges to 3,3-dimethyl-2-butanone (pinacolone): HO OH H₂C-C-C-CH3 CH3 H₂O* C-C-CH3 + H₂O H3C CH3 H₂C CH3 pinacol pinacolone Draw structural formulas for the two carbocation intermediates in this reaction. . You do not have to consider stereochemistry. Do not include counter-ions, e.g., Na+, I, in your answer. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures using the sign from the drop-down menu.
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