Using Friedel Crafts alkylation of benzene, a group of scientists discovered marks) compound A, C10H120, an optically inactive compound. They discovered that compound B, C10H12CIO, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C10H16CINO3, is formed. While Friedel Crafts alkylation of compound A produces compound D. This compound D was oxidised to produce compound E, CH203 as a major product. Compound F, C12H1402, was produced by Friedel Crafts acylation of compound A. This compound F reacts positively with alkaline iodine and 2,4- dinitrophenylhydrazine. However, it returns negative results for Tollens' and Benedict's tests. Prolonged heating of compound F with acidified potassium manganite (VII) produces compound G, CH.04 (aromatic dicarboxylic acid compound) as a major product and minor products (carbon dioxide and water). Identify the possible structural formulae compounds A to G. How would you distinguish between compounds E and G?

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
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.37P
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Using Friedel Crafts alkylation of benzene, a group of scientists discovered marks) compound A, C10H120, an optically inactive compound. They discovered that compound B, C10H12CIO, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C10H16CINO3, is formed. While Friedel Crafts alkylation of compound A produces compound D. This compound D was oxidised to produce compound E, CH203 as a major product. Compound F, C12H1402, was produced by Friedel Crafts acylation of compound A. This compound F reacts positively with alkaline iodine and 2,4- dinitrophenylhydrazine. However, it returns negative results for Tollens' and Benedict's tests. Prolonged heating of compound F with acidified potassium manganite (VII) produces compound G, CH.04 (aromatic dicarboxylic acid compound) as a major product and minor products (carbon dioxide and water). Identify the possible structural formulae compounds A to G. How would you distinguish between compounds E and G?

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