Compound A (C,H12) absorbed 3 equivalents of H2 on catalytic reduction over a palladium catalyst to give hydrocarbon B (C,H19). Upon ozonolysis, compound A gave, among other things, a ketone that was identified as cyclohexanone. Upon treatment with an NaNH2 in liquid NH3 followed by addition of iodomethane, compound A gave a new hydrocarbon C (C10H14). What is the structure of starting Compound A? Compound C C10H14 1) NaNH,/NH3(/) 2) CH3I Compound A C9H12 H, (3 equiv.) Pd/C Compound B C9H18 1) O3 |2) Zn/ACOH, Н,0 other compounds cyclohexanone

Compound A (C,H12) absorbed 3 equivalents of H2 on catalytic reduction over a palladium catalyst to give hydrocarbon B (C,H19). Upon ozonolysis, compound A gave, among other things, a ketone that was identified as cyclohexanone. Upon treatment with an NaNH2 in liquid NH3 followed by addition of iodomethane, compound A gave a new hydrocarbon C (C10H14). What is the structure of starting Compound A? Compound C C10H14 1) NaNH,/NH3(/) 2) CH3I Compound A C9H12 H, (3 equiv.) Pd/C Compound B C9H18 1) O3 |2) Zn/ACOH, Н,0 other compounds cyclohexanone

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 A (C9H12) absorbed 3 equivalents of H2 on catalytic reduction over a palladium catalyst to give B(C9H18). On ozonolysis, compound A gave, among other things, a ketone that was identified as cyclohexanone. Ontreatment with NaNH2 in NH3, followed by addition of iodomethane, compound A gave a new hydrocarbon, C(C10H14 ) . What are the structures of A, B, a nd C?
Compound A (C9H12) absorbed 3 equivalents of H2 on catalytic reduction over apalladium catalyst to give B (C9H18). On ozonolysis, compound A produced 3 products, C, Dand E which was a ketone identified as cyclohexanone. On treatment with NaNH2 in NH3,followed by addition of iodomethane, compound A gave new hydrocarbon, F (C10H14). Drawstructures of A, B, C, D and F.
Compound A (C9H12) absorbs three equivalents of H2 on a Catalina reduction over a palladium catalyst to give propylcyclohexane. On ozonolysis, compound A give the two products shown below. On treatment with NH2 , NH3 followed by addition of 1_bromo4methylpentane, compound A gave a new hydrocarbon,B (c5H24 ). What are the structures of compound A and B?
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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. What is the isometric pair of A and B that corresponds?
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?
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Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.
Isoerythrogenic acid, C18H26O2, is an acetylic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.