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- As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wöhler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?Give the Reagents. KMN04 O 1) LIAIH4, 2) H3O+ O periodinane O 1) MgCI, 2) H3O+OH - NH, Br2/KOH →product; 1. (a-hydroxy amide) Product of this Hoffmann bromamide reaction is : OH (a) Ph – Ĉ-CH3 (Ъ) Ph — CHO (c) Ph- CH3 (d) Ph – CH2 -NH2 NO2
- а) Consider the reaction scheme below. PhLi HONH,, HCI A ELOH B (i) Deduce the structures of compounds A, D and intermediate C. (ii) Outline the mechanism for the conversion of A to B. b) Pyrrole and indole both react with the reagents shown below to give compounds E and F respectively. Reagents: POC13, NazCO3, H2O N. E F (i) (ii) (iii) Show how the electrophile is generated. Account for the regioselectivity observed. Complete the mechanism for the formation of compound F.Provide the missing reagent indicated by "???" CI ??? OH (+ other products)6B. Write a reaction scheme to selectively synthesize the following: OH OMe H3C OMe
- (d) Propose a reaction mechanism to account for the following reaction. AIC3Provide the products for the reactions shown below. Suggest a reasonable mechanism (show electron flow or provide a brief explanation) to account for each step, paying attention to stereochemical details. (a) OBn 1. EtO)2CO, NaOEt 2. H* 3. H₂O*, heat 1. NaH, THF 2. Br, THFGive the major organic product(s) for each of the following reactions (a) + H2 1. (CF3CO0)2Hg. CH3OH (b) 2, NABH4
- Propose and illustrate detailed mechanisms to complete thenfollowing reactionI. Predict the products of each of the following reactions: (REWRITE THE WHOLE EQUATION) (a) PHARMACEUTICAL ORGANIC CHEMISTRY (c) 1) BH, THF 2) H₂O₂, NaOH ? 1) CH₂CO3H 2) H₂O* ? (b) (d) Papill ? 1) OsO4 2) NaHSO /H₂O ?7. (Chapter 15 - Q41a) Propose a structure for the compound that fits the following description. Ca0H14 7.18 5, (4H, broad singlet) 2.70 8 (4H, quartetJ =7 Hz) 1.20 5 (6H. triplet J =7 Hz) IR: 745 cm1 7(a) IR absorption indicate the compound is -disubstituted = 7(b) The name of the compound is