Question

Questions and Problems 553 ation for the reaction that would produse cach of the following amines b. N.Methylpropanamine c. N.N-Diethylpentanamine 15.37 Briefly explain why the lower molar massamines (lewer than five carbons) exhibit appreciable solubility in water 15.38 Why is the salt of an amine appreciably more soluble in water than the mine from which it was formed 15.39 Most drugs containing amine groups are not administered as the mine but rather the amount you suggeste son why? 15.40 Why does aspirin upset the stomach, whereas acetaminophen (Tylenol does not? 15.41 Putrescine and cadaverine are two odoriferous amines that are produced by decaying flesh. Putrescine is 1.4-butanodiamine and cadaverine is 1.5-pemandiamine. Draw the structures of these two compounds. 15.42 How would you quickly convert an alkylammonium salt into a water-insoluble amine? Explain the rationale for your answer. 15. Drew the condensed formula for each of the following a. Proponamide b. N.N-Diethylhutanamide d. N-Methylhexanamide 15.56 Draw the condensed formula for each of the following amides a. N.Propylbutanamide CN Methylpropanamide b. N.Butyloctanamide d. N.Isopropylhexanide 15.57 Draw the condensed formula and line formula of each of the following amides: Ethanamide h. N. Methylpropanamide C.N.N.Diethylenenamide d. -Bromo-4-methylhexamide e. N N-Dimethylacetamide 15.58 Draw the condensed formula and line formula of each of the foll- lowing amides: . Acetamide h. 4. Methylpentanamide G. NON-Dimethylpropanamide d. Formamide 6. N-Expropionamide 15.59 The active ingredient in many insect repellents is N N-etyl- toluamide (DEET). Draw the structure of this compound. Which carboxylic acid and amine would be released by hydrolysis of this compound? 15.60 When an acid anhydride and an amine are combined, an amide is formed. This approach may be used to synthesire acetaminophen. the active ingredient in Tylenol Using the reactants provided here, draw the tructure of the amide product caminophen: Heterocyclic Amines 15.43 Indole and pyridine rings are found in alkaloids. R. Sketch each ring. b. Name one compound containing each of the ring structures and indicate itsuse 15.44 What is an alkaloid 15.45 List some heterocyclic amines that are used in medicine 15.46 Distinguish between the l i cendanesthetic CH,C-o-OCH,+ 2HN- Amides Foundations 15.47 Why do amideshwarya 15.4 Describe the water t e r tion to their carbon chain length 15.49 Explain the IUPAC nomenclatures for naming des 15.50 How are the common names of amides derived 15.51 Describe the physiological cllects of babies. 15.52 Why is acetaminophen often recommended in place of aspirin? Applications 15.53 Use the IUPAC and comme systems of somenclature to name the following amides: 15.61 Explain why amides are neutral in the acid-base sense 15.62 The amide bond is stabilized by resonance Draw the contribut ing resonance forms of the amide boed. 15.63 Lidocaine is often used as a local anesthetic. For medicinal pur- poses, it is often used in the form of its hydrochloride salt became the salt is water soluble. In the structure of lidocaine hydrochloride shown, locate the amide functional group NH-C-CH-N-CH.CH, CH, A CB, CHẠCH, = CHCHONH & CHÊN HÀI 154 1. CH CH CH CH.CH the IUPAC Nomenclature System to name cach of the fol lowing amides 15.64 Lacate the amine functional group in the structure of lidocaine is lidocaine a primary secondary, or tertiary amine 15.65 The antibiotic penicillin BT botais functional rounds cussed in this chapter. In the structure of penicillin BT shown, located name as many functional groups as you can COOH CH, ICH CH_CH. SCH.CONH .. CH CH.CHCHENK -CNH PBT

Answer 1

15.53 la , CH₂ CH₂ - CNH - Dewpanamide 1 (6) CH, CH2 C4, C4, CANH © CH3 - NICU), pentanamide NUN-Dimethyl ethenamide 15.54 a CH₃CH₂Cų ch- S 1 B 2 C- . 3-Beemopentanami de 3-Bromo benzamide 2-methyl peupainamide Cha-ch-C Nu, 3 cm 4 3 2 1 1 15.55 lai peopernamide CH₂ CH - EN (6 N, N dimethyl buta namide ₃ CH₃ CH₂ CH CH(CH3)2 6 2,3-diethyl pentananide CH3 CH₂ - Ch-ch- & NU- cet Et la I N-methy hexaneinide - CH₂ Ch, cucu,cu CNU(CU) 0 5 4 3 2 15.56 (a) N-peopyl butachaimide (6 N-butyl octanamide CH₂ ch, chic nch cho e Canal o N-methy! peopelhamide ch - CH₂ CH₂ch, -C- e 7 ( 22 Ch ₂ CH₂ Chine I puupahamice > CH3 CH-CNUCU