19.60 Draw the major organic products for each of the following reactions. (a) (b) OEt LOCH3 Pd(PPH3)4, NaOH EtO Pd(PPh)4, NaOH -? THE THE (c) (d) Pd(OAc)2 Pd(OAc)2. ? PPH3,EtgN ? PPH3,EtgN Br
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- (−)-Hyoscyamine, an optically active drug used to treat gastrointestinal disorders, is isolated from Atropa belladonna, the deadly nightshade plant, by a basic aqueous extraction procedure. If too much base is used during isolation, optically inactive material is isolated. (a) Explain this result by drawing a stepwise mechanism. (b) Explain why littorine, an isomerisolated from the tailower plant in Australia, can be obtained optically pure regardless of the amount of base used during isolation.(−)-Hyoscyamine, an optically active drug used to treat gastrointestinal disorders, is isolated from Atropa belladonna, the deadly nightshade plant, by a basic aqueous extraction procedure. If too much base is used during isolation, optically inactive material is isolated. (a) Explain this result by drawing a stepwise mechanism. (b) Explain why littorine, an isomer isolated from the tailflower plant in Australia, can be obtained optically pure regardless of the amount of base used during isolation.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. Given the structure of quinapril, which one of these two products isneeded to synthesize the drug?
- tert-Butoxycarbonyl azide was developed as a reagent for peptide synthesis at OWL's home institution, the University of Massachusetts, by Prof. L.A. Carpino. It is prepared by treating tert-butoxycarbonyl chloride with sodium azide. Propose a structure for the initially-formed intermediate in this reaction.The analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Write the structure of each intermediate. Explain why a racemic product is formed.Explain the reaction for the formation of acetal and hemiacetal. Explain why N,N-disubstituted amide is less acidic than ester. Why only methyl ketone do undergoes haloform reaction. LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?
- Attenol A and pinnatoxin A are natural products isolated from marine sources. (a) Locate the acetals, hemiacetals, imines, and enamines in both compounds. (b) Draw the hydrolysis product formed when attenol A is treated with aqueous acid. Include stereochemistry at all stereogenic centers.The analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Draw the structure of each intermediate. Explain why a racemic product is formed.Hypoglycin A, an amino acid derivative found in unripened lychee, is anacutely toxic compound that produces seizures, coma, and sometimesdeath in undernourished children when ingested on an empty stomach. (a) Draw the neutral, positively charged, and negatively charged forms of hypoglycin A. (b) Which form predominates at pH = 1, 6, and 11? (c) What is the structure of hypoclycin A at its isoelectric point?
- Although codeine occurs in low concentration in the opium poppy, most of the codeine used in medicine is prepared from morphine (the principal component of opium) by the following reaction. Explain why selective methylation occurs at only one OH in morphine to give codeine. Codeine is a less potent and less addictive analgesic than morphine.Compound A is a derivative of the carbohydrate perosamine, which is found in the antibiotic perimycin. When A is treated with acetic anhydride in methanol, a monoacyl derivative B (C9H17NO5) is obtained in 73% yield. What is the structure of compound B?Devise a synthesis of benzocaine, ethyl p-aminobenzoate (H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any needed organic or inorganic reagents. Benzocaine is the active ingredient in the topical anesthetic Orajel (Section 18.15C).