The first step in the mechanism for the reaction of an amine with a carboxylic acid to produce an amide is: A) N2 loss B) an acid-base reaction C) loss of C02 D) a nucleophilic attack on the carbonyl carbon E) loss of H20
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- Reductive amination requires a hydrogen on the carbonyl carbon to proceed BECAUSE Reductive amination converts only aldehydes to aminesSafrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4- methylenedioxymethamphetamine, “Ecstasy”) by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine.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 Tamoxifen
- Synthadotin is a promising anticancer drug in clinical trials. a.Identify the functional groups. b.Classify any amine or amide as 1°, 2°, or 3°. c.At which sites can synthadotin hydrogen bond to another molecule like itself? d. Label two nucleophilic sites. e. Label two electrophilic sites. f. What product is formed when synthadotin is treated with HCl?TRUE OR FALSE: Reductive amination is a 1-step reaction with a Nu adding to the carbonyl carbon and the intermediate is reduced by NaBH4.Rank the labeled N atoms in the anticancer drug imatinib (trade nameGleevec) in order of increasing basicity. Imatinib, sold as a salt withmethanesulfonic acid (CH3SO3H), is used for the treatment of chronicmyeloid leukemia as well as certain gastrointestinal tumors.
- 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?Thioglycolic acid, HSCH2CO2H, a substance used in depilatory agents (hair removers) has pKa = 3.42. What is the percent dissociation of thioglycolic acid in a buffer solution at pH = 3.0?Part A: Draw the product of the reaction of propylamine with water Part B: Draw the product of the neutralization of propylamine with HBr Part C: Draw the product of the reaction of N-methylaniline with water
- Draw the following a) N-methylpropanamideb) cis-2-heptenec) 2-hexanone d) butylbutanoatee) 3-chloropentanoic acid f) 2,2-dibromo-butanalg) 2-octanolh) 1-propynei) butylethylmethylamine j) butylpropyletherWhich of the following reaction or reagent does not produce an amine molecule? A. Curtius rearrangementB. Reaction of oximes with metallic sodium in ethanolC. Reaction of N-alkylphthalimide with hydrazineD. Hofmann transformationE. Wolff transformationWhich of the following reactions represents the most likely reaction of naproxen with water? a.) C14H14O3(aq) + H2O(l) ⇄C14H13O3-(aq) + OH-(aq) b.) C14H14O3(aq) + H2O(l) ⇄C14H15O3+(aq) + OH-(aq) c.) C14H14O3(aq) + H2O(l) ⇄ C14H13O3-(aq) + H3O+(aq) d.) C14H14O3(aq) + H2O(l) ⇄C14H15O3+(aq) + H3O+(aq)