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

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter18: Ethers And Epoxides; Thiols And Sulfides

Section18.SE: Something Extra

Problem 36MP: Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds...

See similar textbooks

Similar questions

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?
Treatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.
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? a. Isomer A is cyclopentene and isomer is 1-pentyne O b. Isomer A is cyclopentene and isomer B is 1-methylcyclobutene c. Isomer A is cyclopentene and isomer B is 3-methylcyclobutene d. Isomer A is 1-methylcyclobutene and isomer B is 3-methylcyclobutene
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?
Compound A, C11H16O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H2SO4, dehydration occurred and an optically inactive alkene B, C11H14 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C8H8O, was shown to be a methyl ketone while product D, C3H6O, was shown to be an aldehyde.
Compound A, C11H16O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H2SO4, dehydration occurred and an optically inactive alkene B, C11H14 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C7H6O, was shown to be an aldehyde while product D, C4H8O, was shown to be a ketone. Draw the structure of compound C. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. HELP PLEASE I DONT UNDERSTAND THE PROCESS
Compound A, C₁1 H160, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H₂SO4, dehydration occurred and an optically inactive alkene B, C₁₁H₁4 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C7H6O, was shown to be an aldehyde while product D, C4H8O, was shown to be a ketone. Draw the structure of compound C. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.
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.
Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?