Amantadine is effective in preventing infections caused by the influenza A virus and intreating established illnesses. It is thought to block a late stage in the assembly of thevirus. Amantadine is synthesized by treating 1-bromoadamantane with acetonitrile insulfuric acid to give N-adamantylacetamide, which is then converted to amantadine.CH,C=Nin H,SO,BrNHCCH3NH21-BromoadamantaneAmantadine(a) Propose a mechanism for the transformation in Step 1.(b) Describe experimental conditions to bring about Step 2.

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Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.47P

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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.
One step in the urea cycle for ridding the body of ammonia is the conversion of argininosuccinate to the amino acid arginine plus fumarate. Propose a mechanism for the reaction, and show the structure of arginine.
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.
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?
Dihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesulfonic acid, ArSO3H. Propose a mechanism for this conversion.
Treatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. Propose a structural formula for compound A.
Show how the synthetic scheme developed in Problem 23.67 can be modified to synthesize this triiodobenzoic acid X-ray contrast agent.
The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.
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.
Azlactones are important starting materials used in the synthesis of dehydro Î±-aminoacids. They react with aldehydes to form an intermediate that is hydrolyzed under acidic conditions to give the final amino acid product. Provide the structure of the intermediate and propose a mechanism for its formation.
Show the products you would obtain by acid-catalyzed reaction of cyclohexanone with ethylamine, CH3CH2NH2, and with diethylamine, (CH3CH2) 2NH.

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