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- 3. Provide a mechanism for the following transformation: Ph CI (2 eq.) 2 eq. NaCN 4. Provide a mechanism for the following transformation: S H₂O NC CN Ph Ph OH of OHDraw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. NH3 (1 equiv)Draw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. [1] NaOH; [2] CH3COCl
- MeO 22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an acetoacetic ester synthesis (Section 19.6). 5 3 6 CH₂O CI acetoacetic ester synthesis HC 7 MeO MeO 1 8 2-Methoxynaphthalene Nabumetone (a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at carbon 5 or 7. (b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum- etone is completed.Draw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with each reagent. With some reagents, no reaction occurs. NaHCO3Which carbonyl groups in the anticancer drug Taxol will undergo nucleophilic addition, and which will undergo nucleophilic substitution?
- The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold Helminthosporium sativum, involves the following base treatment of a keto tosylate. What kind of reaction is occurring? How would you complete the synthesis?What product is formed when each compound is treated with either Ag2O, NH4OH or Na2Cr2O7, H2SO4, H2O?Please give the appropriate reagents to complete the following synthesis. 1 2 3
- Treatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Br forms compound X. This reaction is the first step in the synthesis of illudin-S, an antitumor substance isolated from the jack-o'-lantern, a poisonous, saffron-colored mushroom. What is the structure of X?Quinapril (trade name Accupril) is used to treat high blood pressure andcongestive heart failure. One step in the synthesis of quinapril involvesreaction of the racemic alkyl bromide A with a single enantiomer of theamino ester B. What two products are formed in this reaction?Give a systemic name for each compound OCH,CH3 (d)
