Using Friedel Crafts alkylation of benzene, a group of scientists discovered compound A, C8H10, an optically inactive compound. They discovered that compound B, C8H9Br, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C3H§BrNO2, is formed. While Friedel Crafts acylation of compound A produces compound E, C10H12O. This compound C was oxidised to produce compound D, C;H4BrNO4 as a major product. Identify the possible structural formulae compounds A to E and explain your answers.

Using Friedel Crafts alkylation of benzene, a group of scientists discovered compound A, C8H10, an optically inactive compound. They discovered that compound B, C8H9Br, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C3H§BrNO2, is formed. While Friedel Crafts acylation of compound A produces compound E, C10H12O. This compound C was oxidised to produce compound D, C;H4BrNO4 as a major product. Identify the possible structural formulae compounds A to E and explain your answers.

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

Chapter22: Reactions Of Benzene And Its Derivatives

Section: Chapter Questions

Problem 22.61P

See similar textbooks

Similar questions

2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (ii) What is the type of reaction involved in the formation of compound W? (iii) Identify the major product of the elimination reaction between compound Xand compound Y based on Zaitsev’s rule.
The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.
(10pts) Compound A, C10H16, was found to be optically active. On catalytic reduction over a palladium catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, CioH2o. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid (CHCOOH). The other fragment, compound C, was an optically active carboxylic acid, C8H14O2. Write reactions, and draw the correct structures for A-C, explain your answer in detail.
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…
An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.
Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.
Benzene, C6H6 undergoes substitution reaction with concentrated nitricacid, HNO3 to produce compound L. The reaction of compound L withbromine, Br2 in the presence of iron tribromide, FeBr3 produced compoundM. Benzene also undergoes Fridel-crafts alkylation reaction withchloroethane, CH3CH2Cl using catalyst N to produce compound P (i) Draw the structural formula of L, M and P (ii) State catalyst N. (iii) Show the formation of electrophile that will be reacted with benzene for theformation of compound P.
Please be clear in your writing, solve step by step Compound A (C9H12), when hydrogenated by catalysis on Pd / C, absorbs 3 equivalents of H2 to give compound B (C9H18). Ozonolysis of compound A gives cyclohexanone (C6H10O). Compound A reacting with NaNH2 / NH3 followed by addition of CH3Br gave compound C (C10H14). What are the structures of compounds A, B, and C?
Compound P (C2H4) which is an alkene undergoes reaction with HCl to produce compound Q (C2H5Cl). Reaction of compound Q with benzene in the presence of AlCl3 as catalyst produces compound R. Then, nitration of compound R in the presence ofnH2SO4 produces two compounds, S and T. But when compound R is reacted with a hot acidified solution of alkaline KMnO4 gives compound U. Deduce the structure of compounds P to U.
A hydrocarbon (X), with the molecular formula: C8H14 is reduced in presence of sodium and liquid ammonia to give the only product (Y) with the molecular formula: C8H16. Compounds X and Y both resulting 2,5-dimethylhexane when treated with hydrogen and platinum catalyst (H2/Pt). As a result of the oxidative cleavage of compound Y (by using KMnO4 / H2SO4), a single carboxylic acid derivative with C4H8O2 molecular formula is formed. Again, as a result of the reaction of Y with perbenzoic acid, the chiral compound C8H14O is observed, but the reaction of compound Y with bromine gives the achiral C8H14Br2 as the product.
When the compound shown below undergoes acid-catalyzed dehydration, a ring expansionoccurs to give the fused-ring product. What type of intermediate is formed in this reaction?Explain the ring expansion in terms of the reaction mechanism
Compound A produce compound D while undergo Friedel Crafts Alkylation. Compound D is then oxidized and produce compound E (C11H12O3) as a major product.What are the possible structural formula of compound D and E?