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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.A student attempted to prepare 1-chlorobutane by mixing 1-butanol with NaCl in acetone. Was the student succesful? Explain.What are the differences in the regioselectivity of lithiation of 2-chloropyridine when it reacts with LDA and [BuLi.LiO(CH2)2(NME2)]?
- Why are the reactions involving 2-chloropyridine with LDA and [BuLi.LiO(CH2)2(NME2)] performed at low temperatures?A. In the synthesis of 1-bromobutane, what is the inorganic by-product left in the reaction flask following the distillation? Why was the bromoalkane the bottom layer in the separatory funnel? B. Predict the product when 1-methylcyclohexanol reacts with H2SO4 and KBr. Show the mechanism.Give at least two methods for the preparation of 2-methylpropene. What happens if it is treated with: a) H2O/H+; b) HBr/ROOR; c) polymerization. In the case of the reaction with H2O/H+ write the mechanism.
- Nitriles, R–=C≡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2C≡N, if it has IR absorptions from 2500–3100 cm-1 and at 1710 cm-1, and has M+=74?Can 4-methylcyclohexanoic acid be reduced by NABH4?True or False 8. Blank determination is employed in the determination of the Koettsdorfer number. 9. Saponification is the alkaline hydrolysis of fatty oils which leads to formation of soaps 10. Esters are composed of carboxylic acids and alcohol.
- Write equations for the reaction of 2-butanol with reagent. Where you predict no reaction, write NR. Q)K2Cr2O7, H2SO4, H2O, heatThe structure of limonene appears in Problem 25-13. Predict the products formed when limonene reacts with the followingreagents.(a) excess HBr (b) excess HBr, peroxides (c) excess Br2 in CCl4(d) ozone, followed by dimethyl sulfide (e) warm, concentrated KMnO4 (f) BH3 # THF, followed bybasic H2O2Write reactions of 2-methylbutene-2 with the following reagents: a. KMnO4/ H2O/20 °C; b. HBr.