23.6 Intramolecular Aldol Reactions Treatment of certain dicarbonyl compounds with base produces cyclic products by intramolecular reaction CH₂ CH3 NaOH Ethanol CH₂ 2,5-Hexanedione 3-Methyl-2-cyclopentenone (a 1,4-diketone) 2,6-Heptanedione (a 1,5-diketone) + H₂O NaOH Ethanol CH3 + H₂O 3-Methyl-2-cyclohexenone

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter25: Biomolecules: Carbohydrates
Section25.SE: Something Extra
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Give the mechanism of the compounds

23.6 Intramolecular Aldol Reactions
Treatment of
certain dicarbonyl
compounds with
base produces
cyclic products by
intramolecular
reaction
CH₂
CH3
CH₂
NaOH
Ethanol
CH₂
2,5-Hexanedione 3-Methyl-2-cyclopentenone
(a 1,4-diketone)
2,6-Heptanedione
(a 1,5-diketone)
+ H₂O
NaOH
Ethanol
CH3
+ H₂O
3-Methyl-2-cyclohexenone
Transcribed Image Text:23.6 Intramolecular Aldol Reactions Treatment of certain dicarbonyl compounds with base produces cyclic products by intramolecular reaction CH₂ CH3 CH₂ NaOH Ethanol CH₂ 2,5-Hexanedione 3-Methyl-2-cyclopentenone (a 1,4-diketone) 2,6-Heptanedione (a 1,5-diketone) + H₂O NaOH Ethanol CH3 + H₂O 3-Methyl-2-cyclohexenone
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