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- Devise a synthesis of (E)-tetradec-11-enal, a sex pheromone of thespruce budworm, a pest that destroys fir and spruce forests, fromacetylene, Br(CH2)10OH, and any needed organic compounds orinorganic reagents.Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.21.95 A student carries out the following sequence of reactions. The IR and 1°C NMR spectra are shown for the product C. Draw structures for A-C. (Remember that the 13C NMR signal at 77 ppm is due to the CDCI3 solvent.) NaOC(CH)3 A (CH3)3COH 1. NaOEt, EtOH 1. NaOH, H,O C В 2. H,0º, A EtO OEt 2. Br(CH,),Br 100 90 80 70 60 – 50 40 - 30 20 C 4500 4000 3500 3000 2500 2000 1500 1000 500 200 175 150 125 100 75 50 25 Wavenumbers (cm-1) Chemical shift (ppm) % Transmittance
- Show how the synthetic scheme developed in Problem 23.67 can be modified to synthesize this triiodobenzoic acid X-ray contrast agent.A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.Amines are converted into alkenes by a two-step process called Hofmann elimination. SN2 reaction of the amine with an excess of CH3I in the first step yields an intermediate that undergoes E2 reaction when treated with silver oxide as base. Pentylamine, for example, yields 1-pentene. Propose a structure for the intermediate, and explain why it readily undergoes elimination.
- Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?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?Brasilenyne is isolated from the digestive gland of the sea hare; it shows significant antifeedant activity. Choose the best reagents to complete the final reaction in the synthesis of brasilenyne. HO U Q A B C SOCI2 pyridine PBr3 DMF NaCl DMF Cl2
- A step in a synthesis of PGE1 (prostanglandin E1, alprostadil) is reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Alprostadil is used as temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation. Propose a mechanism for formation of This bromolactone, and account for the observed stereochemistry of each substituent on the cyclohexane ring.Propose a synthesis of the topical anesthetic cyclomethycaine from 4-hydroxybenzoic acid, 2-methylpiperidine, and any other necessary reagents. HN' + HO. НО Cyclomethycaine 4-Hydroxybenzoic acid 2-MethylpiperidineDevise a synthesis of (E)-tetradec-11-enal, a sex pheromone of the spruce budworm, a pest that destroys fir and spruce forests, from acetylene, Br(CH2)10OH, and any needed organic compounds or inorganic reagents.