What is the organic product formed in the following sequence of reactions? Br (1) Mg/ether, (2) CO₂ HOCH₂/H+ (1) DIBAL-H, toluene, -78°C (2) H*(aq) heat (3) H*(aq) II I H IV H ?
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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?Electrostatic potential maps of anisole and thioanisole are shown. Which do you think is the stronger acid, p-methoxybenzoic acid or p-(methylthio)benzoic acid? Explain.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)
- (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,—OHExplain this result: Acetic acid (CH3COOH), labeled at its OH oxygen with the uncommon 18O isotope (shown in red), was treated with aqueous base, and then the solution was acidified. Two products having the 18O label at different locations were formed.LDA/THF, 78°Clongrightarrow Predict the major product of the following a- halogenation/a - alkylation reactions under the given reaction conditions.
- When 3-methyl-1-butene is reacted with 9-borabicyclo[3.3.1]nonane, the "1-ol" product is formed. What is the detailed reactin scheme for the transformation? Describe the purification procedure.Explain this result: Acetic acid (CH3COOH), labeled at its OH oxygen with the uncommon 18O isotope (shown in red), was treated with aqueousbase, and then the solution was acidified. Two products having the 18Olabel at different locations were formed.Tunicates are marine animals that are called "sea squirts" because when they are taken out of water, they tend to contract and expel seawater. Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting by-product (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 3390–3400):
- Rank the species below in order of increasing nucleophilicity in protic solvent. I. H2O II. CH3S— III. CH3COO— IV. t-BuO— I, II, IV, III I, III, II, IV I, III, IV, II I, II, III, IVComplete the reaction: 42K19 → + β + [a]_____________An inexperienced graduate student treated dec-5-ene with borane in THF, placed the flask in a refrigerator, and left for aparty. When he returned from the party, he discovered that the refrigerator was broken and that it had gotten quite warminside. Although all the THF had evaporated from the flask, he treated the residue with basic hydrogen peroxide. Tohis surprise, he recovered a fair yield of decan-1-ol. Use a mechanism to show how this reaction might have occurred.(Hint: The addition of BH3 is reversible.)