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- a. b. 22.16 Using ammonia as your source of nitrogen, show the reagents you would use to prepare each of the following amines: C. d. e. O f. PRACTICE the skill H Answer xi -N -NH₂ H O 1) [H*] NaBH₂CN NH3 2) [H*] NaBH3CN CH3CHOAnswer the following questions about atomoxetine, a drug used to treatattention deficit hyperactivity disorder (ADHD). a.) What amides can be reduced to form atomoxetine?b.) What starting materials can be used to form atomoxetine by reductiveamination? Draw all possible methods.c.) What products are formed by Hofmann elimination of atomoxetine?What carbonyl compound and amine or alcohol are needed to prepare each product?
- 16.20 Give an acceptable name for each carbonyl compound depicted in the ball-and-stick models. a. b.1. Rank the following nitrogens or amines in order of decreasing basicity (strongest to weakest, strongest = 1) a) N 'NH2 compare the basicity of three nitrogen in 1-methylhistamine b) F. 'NH2 'NH2 'NH218.35 Draw the structure of each ammonium salt. a. dipropylammonium chloride b. butylammonium bromide c. ethyldimethylammonium hydroxide 13
- 18.61 Below are two hypothetical compounds. -S N. N. (a) Which compound would you expect to hold greater promise as a potential antihistamine? Explain your choice. (b) Do you expect the compound you chose (in part a) to exhibit sedative properties? Explain your reasoning.Answer the following questions about benzphetamine, a habit-forming diet pill sold under the trade name Didrex. a. Label the stereogenic center(s). b. What amide(s) can be reduced to form benzphetamine? c. What carbonyl compound and amine can be used to make benzphetamine by reductive amination? Draw all possible methods. d. What products are formed by Hofmann elimination from benzphetamine? Label the major product. benzphetamine20.58 Fluphenazine is an antipsychotic drug that is administered as an ester prodrug via intramuscular injection: CF3 Fluphenazine decanoate The hydrophobic tail of the ester is deliberately designed to enable a slow release of the prodrug into the bloodstream, where the prodrug is rapidly hydrolyzed to produce the active drug. (a) Draw the structure of the active drug. (b) Draw the structure of and assign a systematic name for the carbox- ylic acid that is produced as a by-product of the hydrolysis step.
- 22.2 Nomenclature of Amines Which of the following correctly names the compound shown? H₂C. CI O ethyl ethyl -methyl-4-chloro-3- methylaniline O4-chloro- ethyl ,3- dimethylaniline ethylmethyl-1-amino-4-chloro- 3-methylbenzene O 4-chloro-1-ethyl-1,3- dimethylanilineWhat carboxylic acid and amine are needed to synthesize the pain reliever phenacetin? Phenacetin was once a component of the over-the-counter pain reliever APC (aspirin, phenacetin, caffeine), but it is no longer used because of its kidney toxicity.In the 1880's, Acetanilide, sold under the name Antifebrin, was widely used as a pain reliever and fever reducer. However, it had many adverse side effects, including cyanosis as a result of methemoglobinemia. The toxic side effects were the result of a small portion of acetanilide being hydrolyzed to aniline. Acetanilide was discontinued and replaced with phenacetin. Later studies show that both acetanilide and phenacetin are metabolized to acetaminophen. This metabolite, which we know as Tylenol, is responsible for the analgesic and antipyretic properties. Part 1: Show a detailed arrow pushing mechanism of the acid catalyzed hydrolysis of acetanilide to aniline Part 2: Propose a synthesis of Acetaminophen from phenol NH NH NH Phenacetin inophen Acetanilide Attach File Browse Local Files Browse Content Collection