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- 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.Rank the species below in order of increasing nucleophilicity in protic solvent. I. H2O II. CH3S— III. CH3COO— IV. t-BuO— I, II, IV, III I, III, II, IV I, III, IV, II I, II, III, IVWhat organic product is formed when 1‑methylcyclopentene is treated with NMMO in the presence of H2O and a catalytic amound of OsO4? Clearly show stereochemistry by drawing a wedge and dashed bond for each chiral carbon. Only draw one stereoisomer if more than one can be formed.
- Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides. One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(CzHs)3). 3SnCl4 + 4Al(C2H5)3 → 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.160 L of SnCl4 (d= 2.226 g/mL) was treated with 0.346 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). What is the theoretical yield in this experiment (mass of tetraethylstannane, Sn(C2H5)4)? If 0.257L of tetraethylstannane (d= 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?Draw the products formed when p-methylaniline (p-CH3C6H4NH2) is treated with each reagent.a. HClb. CH3COClc. (CH3CO)2Od. excess CH3Ie. (CH3)2C = Of. CH3COCl, AlCl3g. CH3CO2Hh. NaNO2, HCli. Part (b), then CH3COCl, AlCl3j. CH3CHO, NaBH3CNAn optically active alkyne A (C10H14) can be catalytically hydrogenated to butylcyclohexane. Treatment of A with EtMgBr liberates no gas. Catalytic hydrogenation of A over Pd/C in the presence of quinoline poison and treatment of the product with O3 and then H2O2 gives an optically active tricarboxylic acid C8H12O6 (A tricarboxylic acids is a compound with three - CO2H groups.). Give the structure of A, and account for all observations.
- Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reactionoccurs.a. H2 + Pd-Cb. H2 + Lindlar catalystc. Na, NH3d. CH3CO3He. [1] CH3CO3H; [2] H2O, HO–f. [1] OsO4 + NMO; [2] NaHSO3, H2Og. KMnO4, H2O, HO–h. [1] LiAlH4; [2] H2Oi. [1] O3; [2] CH3SCH3j. (CH3)3COOH, Ti[OCH(CH3)2]4, (–)-DETk. mCPBAl. Product in (k); then [1] LiAlH4; [2] H2OOximene 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.Epoxidation of the attached allylic alcohol using the Sharpless reagentwith (−)-DET gives two epoxy alcohols in a ratio of 87:13. a.) Assign structures to the major and minor product.b.) What is the enantiomeric excess in this reaction?
- Hydrogenation of alkene A with D2 in the presence of Pd-C affords a single product B. Keeping this result in mind, what compound is formed whenA is treated with each reagent: (a) mCPBA; (b) Br2, H2O followed by base? Explain these results.A chiral amine A having the R conguration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3, to form CH2 = O and CH3CH2CH2CHO. What are the structures of A and B?Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides.One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(C2H5)3). 3SnCl4 + 4Al(C2H5)3 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.230 L of SnCl4 (d = 2.226 g/mL) was treated with 0.396 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). If 0.335 L of tetraethylstannane (d = 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?