9) a) Diagram the acid (H3O+) catalyzed enolizaton of acetaldehyde. . b) Diagram the base (OH-) catalyzed formation of cyclopentanone from its enol form.
9) a) Diagram the acid (H3O+) catalyzed enolizaton of acetaldehyde. . b) Diagram the base (OH-) catalyzed formation of cyclopentanone from its enol form.
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Transcribed Image Text:9) a) Diagram the acid (H3O+) catalyzed enolizaton of acetaldehyde. .
b) Diagram the base (OH-) catalyzed formation of cyclopentanone from its enol form.
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Step 1
The acid (H3O+) catalyzed enolization of acetaldehyde and the base (OH-) catalyzed formation of cylcopentanone from its enol form are to be drawn.
The aldehyde and ketones can be tautomerizes to their enol form. Because of the acidity of α hydrogens carbonyls undergo keto-enol tautomerism. Tautomers are rapidly interconverted constitutional isomers, and distinguished by a different bonding location for a labile hydrogen atom and a differently located double bond.
The acid catalyzed reaction of aldehyde or ketone proceeds through protonation of carbonyl oxygen.
The base catalyzed reaction of conversion of enol to aldehyde or ketone proceeds with removal of the hydrogen bonded to carbonyl oxygen.
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