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. но. CH,0. [1 кон H [2] CH3I H. CH3 H Ho morphine H. CH3 Ho codeine
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- The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Show how this same synthetic strategy can be used to prepare ethosuximide and methsuximide.The reaction of an ester with an amine is not as slow as the reaction of an ester with water or an alcohol. Explain with reason. Explain why the rate of aminolysis of an ester cannot be increased by H+, OH- or OR-. How can you activate the carboxylic acid? Is acid catalyzed hydrolysis of acetamide a reversible or an irreversible reaction. Explain.The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols. a. Why does the Ritter reaction not work with primary alcohols? b. Provide an explanation for why an amide is less susceptible to nucleophilic attack than its corresponding ester.
- Kindly draw the product that was fromed when phenylacetic acid was treated with the reagent, show the process and give some explanation. Thanks! a. [1] SOCI2; [2] CH3CH2CH2NH2 (excess) b. [1] SOCI2; [2] (CH3)2CHOHTriethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA. a. Explain why it can be used only under slightly acidic conditions. b. Explain why it can cross-link DNA.Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA. a. Explain why it can be used only under slightly acidic conditions.b. Explain why it can cross-link DNA.
- 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 Tamoxifen1. Put these three common types of carbonyl compound in order of decreasing reactivity ester amide acid chloride 2. For the least reactive, show the interconversion to its other resonance form: How does this electron delocalisation make it stable? 3. For the most reactive, draw the mechanism of its undergoing hydrolysis (reaction with H2O): Why makes this type of carbonyl so reactive to nucleophiles?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?
- (a) Explain how NaBH4 in CH3OH can reduce hemiacetal A to butane-1,4-diol (HOCH2CH2CH2CH2OH). (b) What product is formed when A is treated with Ph3P = CHCH2CH(CH3)2? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects.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?a. Rank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acyl substitution reaction (formation of thetetrahedral intermediate): b. Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl substitution reaction (collapse of thetetrahedralintermediate).