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Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0 °C, followed by treatment with N,N-diethylaniline.
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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.Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with N,N-diethylaniline.Phenyl 4-aminosalicylate is a drug used in the treatment of tuberculosis. Propose a synthetic route for this compound starting from 4-nitrosalicylic acid. The synthesis involves multiple steps. Specify all the reagents and the reaction conditions it may require in each step.
- Benzene underwent a Friedel–Crafts acylation followed by a Wolff–Kishner reduction. The product gave the following 1H NMR spectrum. What acylchloride was used in the Friedel–Crafts acylation?Propose a mechanism for the reaction of bisphenol A with phosgene.How will you prepare N-Ethyl-2-phenylethanamine?
- Benzene underwent a Friedel–Crafts acylation followed by a Wolff–Kishner reduction. The product gave the following 1H NMR spectrum. What acyl chloride was used in the Friedel–Crafts acylation?2,6-Dimethoxybenzoic acid was needed for a synthesis of the β-lactam antibiotic methicillin. Show how this carboxylic acid could be synthesized from 2-bromo-1,3-benzenediol.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?
