3. Isoerythrogenic acid, C18H26O2, is an acetylenic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.43P
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3. Isoerythrogenic acid, C18H26O2, is an acetylenic fatty acid that turns a vivid blue on
exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar
equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced.
Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O,
malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde
carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.
Transcribed Image Text:3. Isoerythrogenic acid, C18H26O2, is an acetylenic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.
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