Chapter 22: Problem 61
Among the first antipsychotic drugs for the treatment of schizophrenia was haloperidol (Haldol), a competitive inhibitor of dopamine receptor sites in the central nervous system.
Chapter 22: Problem 61
Among the first antipsychotic drugs for the treatment of schizophrenia was haloperidol (Haldol), a competitive inhibitor of dopamine receptor sites in the central nervous system.
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Get started for freePyrrole undergoes electrophilic aromatic substitution preferentially at the 2 position as illustrated by the synthesis of 2 -nitropyrrole. Write resonance contributing structures for the intermediate formed by attack of \(\mathrm{NO}_{2}^{+}\) at the 2 and 3 positions of pyrrole. From examination of these intermediates, offer an explanation for preferential nitration at the 2 position.
The following groups are ortho-para directors.
(a) \(-\mathrm{OH}\)
(b) \(-\mathrm{OCCH}_{3}\)
(c) \(-\mathrm{N}\left(\mathrm{CH}_{3}\right)_{2}\)
(d) \(-\mathrm{NHCCH}_{3}\)
(e)
Diazepam, better known as Valium, is a central nervous system (CNS) sedative/ hypnotic. As a sedative, it diminishes activity and excitement and thereby has a calming effect. Back in 1976, based on the number of new and refilled prescriptions processed, diazepam was the most prescribed drug in the United States. Following is a retrosynthetic analysis for a synthesis of diazepam. Note that the formation of compound B involves a Friedel-Crafts acylation. In this reaction, it is necessary to protect the \(2^{\circ}\) amine by prior treatment with acetic anhydride. The acetyl-protecting group is then removed by treatment with aqueous \(\mathrm{NaOH}\) followed by careful acidification with \(\mathrm{HCl}\). (a) Given this retrosynthetic analysis, propose a synthesis for diazepam. (b) Is diazepam chiral? If so, how many of the possible stereoisomers are formed in this synthesis?
Following is a retrosynthetic analysis for the acaracide (killing mites and ticks) and fungicide dinocap. (a) Given this analysis, propose a synthesis for dinocap from phenol and 1 -octene. (b) Is dinocap chiral? If so, which of the possible stereoisomers are formed in this synthesis?
Write a stepwise mechanism for each of the following reactions. Use curved arrows to show the flow of electrons in each step.
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