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- One synthesis of the cholesterol-lowering drug atorvastatin involves the construction of the pyrrole by reaction of diketone X with amine Y. Draw a stepwise mechanism for this reaction.Vitamin C is a stable enediol. Draw the structure of the two ketotautomers in equilibrium with the enediol, and explain why the enediol ismore stable than the other tautomersAn allylic alcohol contains an OH group on a carbon atom adjacent to aC—C double bond. Treatment of allylic alcohol A with HCl forms amixture of two allylic chlorides, B and C. Draw a stepwise mechanismthat illustrates how both products are formed.
- Reaction of benzylmagnesium chloride with formaldehyde yieldsalcohols N and P after protonation. Draw a stepwise mechanism thatshows how both products are formedSalsolinol is a naturally occurring compound found in bananas,chocolate, and several foods derived from plant sources. Salsolinol isalso formed in the body when acetaldehyde, an oxidation product of theethanol ingested in an alcoholic beverage, reacts with dopamine, aneurotransmitter. Draw a stepwise mechanism for the formation ofsalsolinol in the following reaction.Identify the lettered compounds in each reaction sequence.Draw the product formed when phenylacetonitrile (C6H5CH2CN) istreated with below reagent. [1] DIBAL-H; [2] H2O
- β-Vetivone is isolated from vetiver, a perennial grass that yields a variety ofcompounds used in traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to β-vetivone by a two-step process: Michael reaction, followed by intramolecular aldol reaction. (a) What Michael acceptor is needed for the conjugate addition? (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal anti-inammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.The products of acidic cleavage of Ethyl isopropyl ether by Hl are: O Al Isopropyl iodide and Ethanol Bi lsapropanol and lodoethane CHisopropane and Ethane DI Mixture of both A and B
- Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal antiinflammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.What carbonyl compound and CBS reagent are needed to prepare X, an intermediate in the synthesis of ezetimibe (trade name Zetia), a drug that lowers cholesterol levels by inhibiting its absorption in the intestines.What neutral nucleophile is needed to convert dihalide A to ticlopidine, an antiplatelet drug used to reduce the risk of strokes?