PART C. Others 33.(5) In the SN1 and SN2 reaction of (R) 2-bromobutane with NaOH, +2.0° of specific rotation was measured from the product, butan-2-ol, CH₂CH(OH)CH₂CH₂. Specific rotation of pure (+)-butan-2-ol is + 15.0°. Please calculate the ratio of SN1 and SN2 reaction rate on 2-bromobutane.
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- (10pts) Compound A, C10H16, was found to be optically active. On catalytic reduction over a palladium catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, CioH2o. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid (CHCOOH). The other fragment, compound C, was an optically active carboxylic acid, C8H14O2. Write reactions, and draw the correct structures for A-C, explain your answer in detail.> acetone > ethane - Two molecular ions H3C-CH₂-CH₂-COR and have undergone McLafferty rearrangement and Ortho effect respectively. What are the possible fragments obtained as a result of these processes ? COOCH3 OH + -COH]: [CH₂O and Co] CO (A) (B) x] : [GH₂C (C) RH, C₂H₂ and CH₂CO: [(CH₂O), CO and CH₂OH] (D) H₂CCROH and C₂H4; [(CH₂O), CO and CH₂OH] R-CH₂-CH₂ - CH₂ - COH H₂C=CR = CROH and H₂C = CH₂ C₂H403 and CH4 P.T.O.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.
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