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- 17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N Tamoxifen3 What are the products of reactions of aldhydes and ketones with (I) chloroform (ii) primary amines? No reagent or reaction condition givenAs 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?
- What starting materials are needed to prepare the compound below by intramolecular Michaelreaction?The formula for the alarm pheromone for one species of ant is C7 H7 O. When treated with I2 and NaOH, this pheromone yields iodoform and n-hexanoic acid. What is the structure of the pheromone?Undecanal is commercially available, but 6-methyl-1-bromoheptane is not. Propose two methods for the synthesis of 6-methyl-1-bromoheptane using precursors containing fewer than five carbon atoms (Cn n < 5). A protecting group will probably be required.
- Enamines formed from the cyclic secondary amine pyrrolidine are important intermediates in the synthesis of 1,5-diketones. (1st pic) On the structures provided below, draw arrows showing electron flow for the reaction mechanism for the acetic acid-catalyzed formation of an enamine from cyclohexanone and pyrrolidine. (2nd pic)The formula for the danger sign pheromone for a species of ant is C7H7O. When treated with I2 NaOH, this pheromone produces iodoform and n-hexanoic acid. How is this pheromone structure?Rank the following compounds in order of increasing basicity: I. p-nitroaniline III. N-methylaniline II. p-aminobenzaldehyde IV. p-methylaniline
- 2. What is the organic by-product in a haloform reaction? A) an ether B) a haloform C) an alcohol D) an ester E) an amideBenzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a Lewis acid such as AlCl3.a. What are the major and minor products of the following reaction?b. Would you expect epoxides to undergo similar reactions?Benzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a Lewis acid such as AlCl3. a. What are the major and minor products of the following reaction? b. Would you expect epoxides to undergo similar reactions?