Using Friedel Crafts alkylation of benzene, a group of scientists discovered compound A, C10H12O, an optically inactive compound. They discovered that compound B, C10H12ClO, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C10H10ClNO3, is formed. While Friedel Crafts alkylation of compound A produced compound D. This compound D was oxidised to produce compound E, C11H12O3 as a major product. Compound F, C12H14O2, 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 test. Prolonged heating of compound F with acidified potassium manganite (VII) produces compound G, C8H6O4 (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
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter10: Organohalides
Section10.SE: Something Extra
Problem 19MP: The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol...
icon
Related questions
Question

Using Friedel Crafts alkylation of benzene, a group of scientists discovered compound A, C10H12O, an optically inactive compound. They discovered that compound B, C10H12ClO, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C10H10ClNO3, is formed. While Friedel Crafts alkylation of compound A produced compound D. This compound D was oxidised to produce compound E, C11H12O3 as a major product. Compound F, C12H14O2, 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 test. Prolonged heating of compound F with acidified potassium manganite (VII) produces compound G, C8H6O4 (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?

Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Carboxylic Acids and their Derivatives
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning
Macroscale and Microscale Organic Experiments
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:
9781305577190
Author:
Kenneth L. Williamson, Katherine M. Masters
Publisher:
Brooks Cole
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning