Following are two possible retrosynthetic analyses for the anticholinergic drug cycri- mine. Fill in the details of each potential synthesis. O: OH + H. Cycrimine (гасemic)
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- 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.Following is an outline of a synthesis of the bronchodilator carbuterol, a beta-2 adrenergic blocker with high selectivity for airway smooth muscle receptors. Q.Why is it necessary to add the benzyl group, PhCH2—, as a blocking group in Step 1?Which 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)
- When an α-hydroxy amide is treated with Br2 in aqueous NaOH under Hofmann rearrangement conditions, loss of CO2 occurs and a chain-shortened aldehyde is formed. The mechanism involves the following steps: Base abstracts an acidic amide proton, yielding amide anion 1; The amide anion reacts with bromine in an α-substitution reaction to give N-bromoamide 2. Abstraction of the remaining amide proton by base gives a resonance-stabilized bromoamide anion 3; Rearrangement occurs to yield isocyanate 4; Water adds to the isocyanate to yield carbamic acid 5; Elimination of CO2 yields carbinolamine 6; Following proton transfer, expulsion of ammonia yields the final product aldehyde. Write out the mechanism and then draw the structures of bromoamide anion 3 and amide anion 1.gas, Cl¬CH2CH2¬S¬CH2CH2¬Cl, was used as a poisonous chemical agentin World War I. Mustard gas is much more toxic than a typical primary alkyl chloride. Itstoxicity stems from its ability to alkylate amino groups on important metabolic enzymes,rendering the enzymes inactive.(a) Propose a mechanism to explain why mustard gas is an exceptionally potent alkylatingagent.(b) Bleach (sodium hypochlorite, NaOCl, a strong oxidizing agent) neutralizes and inactivates mustard gas. Bleach is also effective on organic stains because it oxidizes coloredcompounds to colorless compounds. Propose products that might be formed by thereaction of mustard gas with bleach.Mustard gas, Cl¬CH2CH2¬S¬CH2CH2¬Cl, was used as a poisonous chemical agentin World War I. Mustard gas is much more toxic than a typical primary alkyl chloride. Itstoxicity stems from its ability to alkylate amino groups on important metabolic enzymes,rendering the enzymes inactive.(a) Propose a mechanism to explain why mustard gas is an exceptionally potent alkylatingagent
- 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.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?
