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- Oxidation of cholesterol converts the alcohol to a ketone. Under acidic or basic oxidationconditions, the C“C double bond migrates to the more stable, conjugated position. BeforeIR and NMR spectroscopy, chemists watched the UV spectrum of the reaction mixture tofollow the oxidation. Describe how the UV spectrum of the conjugated product, cholest-4-en-3-one, differs from that of cholesterolQ2: Give the structure of the possible Claisen condensation product from the following reaction .Tell which , If any you would expect to predominate in each case .(a) CH3CO2Et + CH3CH2CO2Et (b) C6H6CO2Et + C6H5CH2CO2Et(c) EtOCO2Et + Cyclohexanones (d) C6H5CHO + CH3CO2EtProvide a reasonable arrow-pushing mechanism for Reaction 5b, and explain the the stereochemical outcome. 5d below
- Complete the following reaction equations :(i) C6H5Cl + CH3COCl →(ii) C2H5NH2 + C6H5SO2Cl →(iii) C2H5NH2 + HNO2 →Predict and draw the major product (C11H12O2) of the following reaction sequence.Acid-catalyzed bromination of pentan-2-one (CH3COCH2CH2CH3) forms two products: BrCH2COCH2CH2CH3 (A)and CH3COCH(Br)CH2CH3 (B). Explain why the major product is B, with the Br atom on the more substituted side of the carbonyl group.
- Give two syntheses for (CH3)2CH¬O¬CH2CH3, and explain which synthesis is betterProvide the mechanism for the conversion shown below. CH3Li is effectively H3C-Li+. What type of mechanism is occuring?(a) What happens when CH3—O—CH<sub3 is heated with HI?(b) Explain mechanism for hydration of acid catalyzed ethene :CH2 = CH2 + HzO CH3—CH,—OH
- Drawing an SN2 product with More Complex Reactants Identify C, the product of an SN2 reaction in the synthesis of raloxifene, a drug used to reduce the risk of invasive breast cancer in postmenopausal women.Which of the following is the product of the reaction shown in Image 17? a. (C6H5)3COH b.C6H5CH2OH c.(C6H5)3CH d.(C6H5)2CHOHThe (+) - aureol is a natural product that has shown selective activity against certain colon and lung cancer cell lines. It is postulated that a key step in the biosynthesis of this substance is the conversion of carbocation A into B. Propose a possible mechanism for this transformation (MUST show the corresponding arrows).