Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data?

Chemistry: Matter and Change
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ISBN:9780078746376
Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
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Chapter22: Substituted Hydrocarbons And Their Reactions
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Problem 69A
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Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data?

a. Isomer A is
cyclopentene and isomer B is 1-pentyne
b. Isomer A is cyclopentene and isomer B is 1-methylcyclobutene
C. Isomer A is 1-methylcyclobutene and isomer B is 3-
methylcyclobutene
d. Isomer A is cyclopentene and isomer B is 3-methylcyclobutene
Transcribed Image Text:a. Isomer A is cyclopentene and isomer B is 1-pentyne b. Isomer A is cyclopentene and isomer B is 1-methylcyclobutene C. Isomer A is 1-methylcyclobutene and isomer B is 3- methylcyclobutene d. Isomer A is cyclopentene and isomer B is 3-methylcyclobutene
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