Both (S)-citronellal and isopulegol are naturally occurring terpenes (S)-citronellal is treated with tin(IV) chloride (a Lewis acid) followed by neutralization with aqueous ammonium chloride, isopulegol is obtained in 85% yield. .When H 1. SnCl4, CHCI, 2. NH,CI (S)-Citronellal (C10H180) Isopulegol (C10H180)
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How many stereocenters are present in isopulegol? How many stereoisomers are possible for a molecule with this number of stereocenters?
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- 4. Compound A has the formula C 8H 8. It reacts rapidly with KMnO 4 to give CO 2 and a carboxylic acid, B (C 7H 6O 2), but reacts with only 1 molar equivalent of H 2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H 2 are taken up and hydrocarbon C (C 8H 16) is produced. What are the structures of A, B, and C.A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under thesame conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C.Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structuresof A, B, and C; give equations for their formation; and explain the stereospecificity of these reactionsCembrene, 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.
- Nitromethane is reacted with ethyl prop-2-enoate with EtO-Na+, EtOH 3 equivalents to give the product X(C16). X then reacts with H2/Raney Ni to give the product Y(C14), which in turn reacts with Na to give Z (C12). Indicate which products X, Y and Z are.An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent ofH2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragmentis propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are thestructures of A, B, and C? Write all reactions and show your reasoning.A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2 CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions.
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- Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula C10H16, both yield 2,6- dimethyloctane when treated with H2 and a Pd catalyst. Ozonolysis of oximene forms (CH3)2C = O, CH2 = O, CH2(CHO)2, and CH3COCHO. Ozonolysis of myrcene yields (CH3)2C = O, CH2 = O, (two equiv), and HCOCH2CH2COCHO. Identify the structures of oximene and myrcene.1. Using Br2 in C2H4Br2 will result in HBr and ______. a. C2H3Cl3 b. C2H4Cl3 c. C2H2Cl3 d. none of the above 2. How many halogenation are posible in propane? a. 3 b. 8 c. 6 d. 10 3.Sulfonation of pentane will result in ________ and water. a. C5H11SO3H b. C5H12SO3H c. C5H14SO3H d. none of the above 4.Nitration of hexane will result in ________ and water. a. C6H13SO3H b. C6H15NO2 c. C6H13NO2 d. C6H14NO2 5.How many moles of O2 in heating a C12H26 (dodecane) a. 27 b. 37 c. 24 d. none of the aboveWrite out all the isomers of the compound with molecular formula C4H10O Select the normal/ primaryisomer and treat it with conc. H2SO4 and heat. Identify the reaction and give the product ‘A’ from it. Treatment of ‘A’ with HCl/H2O gives ‘B’ Treatment of ‘A’ with cold KMnO4/ -OH gives ‘C’ Treatment of ‘A’ with Hot KMnO4/-OH gives ‘D’ followed by acidification of the mixture to give ‘E’