Compound A has the formula CioH16 On catalytic hydrogenation over palladium, it reacts with only one molar equivalent of Hz. Compound A also undergoes reaction with ozone, followed by zinc-acetic acid treatment, to yield a symmetrical diketone B (C10H602). A 1) O3 2) Zn/CH;COOH H2 (1 mole) / Pd saturated hydrocarb C10H1602 C10H16 What is the structure of compound A?

Compound A has the formula CioH16 On catalytic hydrogenation over palladium, it reacts with only one molar equivalent of Hz. Compound A also undergoes reaction with ozone, followed by zinc-acetic acid treatment, to yield a symmetrical diketone B (C10H602). A 1) O3 2) Zn/CH;COOH H2 (1 mole) / Pd saturated hydrocarb C10H1602 C10H16 What is the structure of compound A?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 50AP: -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the...

See similar textbooks

Similar questions

α-Terpinene, C10H16, is a pleasant-smelling hydrocarbon that has been isolated from oil of marjoram. On hydrogenation over a palladium catalyst, α-terpinene reacts with 2 molar equivalents of H2 to yield a hydrocarbon, C10H20. On ozonolysis, followed by reduction with zinc and acetic acid, α-terpinene yields two products, glyoxal and 6-methyl-2,5- heptanedione. (a) How many degrees of unsaturation does a-terpinene have? (b) How many double bonds and how many rings does it have? (c) Propose a structure for a-terpinene.
Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV absorption at 245 nm, but dihydrocembrene (C20H34), the product of hydrogenation with 1 equivalent of H2, has no UV absorption. On exhaustive hydrogenation, 4 equivalents of H2 react, and octahydrocembrene, C20H40, is produced. On ozonolysis of cembrene, followed by treatment of the ozonide with zinc, four carbonylcontaining products are obtained: Propose a structure for cembrene that is consistent with its formation from geranylgeranyl diphosphate.
-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.
Ozonolysis (O3 in CH2Cl2) of compound A under reducing conditions (Zn /acetic acid) gives formaldehyde, 2-butanone, and compound B. Catalytic hydrogenation (H2/Pd) of A gives 2,7-dimethylnonane. What is a possible structure for compound A? a. 2,7-Dimethyl-2,8-nonadieneb. 2,7-Dimethyl-1,8-nonadienec. 2,7-Dimethyl-1,6-nonadiened. 2,7-Dimethyl-1,7-nonadiene
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr) which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (Ch3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which reacts with 2 equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and Pt catalyst to give 2-methylpropylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.
Alcohol A (C10H18O) is converted to a mixture of alkenes B and C on being heated with potassium hydrogen sulfate (KHSO4). Catalytic hydrogenation of B and C yields the same product. Assuming that dehydration of alcohol A proceeds without rearrangement, deduce the structures of alcohol A and alkene C.
An achiral hydrocarbon A of molecular formula C7H12 reacts with two equivalents of H2 in the presence of Pd-C to form CH3CH2CH2CH2CH(CH3)2. One oxidative cleavage product formed by the treatment of A with O3 is CH3COOH. Reaction of A with H2 and Lindlar catalyst forms B, and reaction of A with Na, NH3 forms C. Identify compounds A, B, and C. Be sure to answer all parts.
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O togive 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3)followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which decolorizestwo equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to giveisobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout
1. write out all the isomers of the compound with molecular formula C4H10O. 2. select the normal/primary isomer and treat it with conc.H2SO4 and heat to produce A. Identify the type of reaction 3. Treatment of A with HCl/H2O gives B and with cold KMnO4/ OH- gives C . Give the name and structures of A, B and C 4. Treatment of A with Hot KMnO4/OH- gives D followed by acidification of the mixture to give E. What is D and E ?
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. (i) Draw the structural formula of compounds W, X and Y
Give the structure of the compound that satisfies the criterion given in each instance: a) A compound of formula C5H11Br that cannotyield analkene upon treatment withtBuOK. b). A four carbon alkene that yields a meso diol upon treatment with m-CPBA/H2O. c). A six carbon secondaryalcohol (C6H14O) that yields only a single alkene upon acid catalyzeddehydration
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2 SO4 gives E (C10 H16), which decolorizes two equivalents of Br2 to give F (C10H16 Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.