Compound ABC is an optically active hydrocarbon with the molecular formula C8H16. Upon hydrogenation over a Platinum catalyst, ABC absorbs exactly one (1) mole of hydrogen gas resulting in the formation of compound DEF (C,H18). Ozonolysis of ABC followed by reductive workup using Zn and dilute acid yields two compounds. These include acetone and compound GHI which is an optically active aldehyde. Propose structures for ABC, DEF, and GHI. DEF H2 Pt АВС 1. O3 2. Zn, H GHI

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
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.55P
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Compound ABC is an optically active hydrocarbon with the molecular formula C3H16. Upon
hydrogenation over a Platinum catalyst, ABC absorbs exactly one (1) mole of hydrogen gas resulting
in the formation of compound DEF (C;H18). Ozonolysis of ABC followed by reductive workup using
Zn and dilute acid yields two compounds. These include acetone and compound GHI which is an
optically active aldehyde. Propose structures for ABC, DEF, and GHI.
DEF
H2
Pt
АВС
1.03
2. Zn, H
GHI
Transcribed Image Text:Compound ABC is an optically active hydrocarbon with the molecular formula C3H16. Upon hydrogenation over a Platinum catalyst, ABC absorbs exactly one (1) mole of hydrogen gas resulting in the formation of compound DEF (C;H18). Ozonolysis of ABC followed by reductive workup using Zn and dilute acid yields two compounds. These include acetone and compound GHI which is an optically active aldehyde. Propose structures for ABC, DEF, and GHI. DEF H2 Pt АВС 1.03 2. Zn, H GHI
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