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- Give the major product for the reaction. Pyrrolidine is a secondary amine. CH CH O CH CH! O OH CH2 O CH. I CH.CH Ї TCH CHE OH CH CH₂CH₂ CH.CH CH.OH2 0= RO pyrrolidine. 2 GH CH2 3 HCI H,0 TOH OH: CH₂CH₂ TCH CH: CH₂CH. CH₂CH₂1. Rank the following amines A-D in order of decreasing basicity, where 1 is the most basic. NO2 A B :ZI3. Which of the following amines will not undergo an acyl substitution reaction with methyl acetate (CH3CO2CH3)? A) NH3 B) H₂N C) H₂N D) H3C-N-CH3 CH3 E) All of these will react with methyl acetate
- 2262 Sat Aor 6 1 Which one of the following compounds is the strongest acid? CNH2 -NH2 -CO2H OH CI- СОН CH CH C A B 2. Which one of the following amines will not produce an amide when mixed with an acid chloride? NH PHCH,NH2 PHNH2 Et,NH A C 3. What is the major product of the following sequence of reactions? CH3 1) NBS, hv (excess) C(OH)3 CHO CO2H CH2O 2) NaOH, H20 (excess) A В C 4. What is the major product of the following intramolecular aldol condensation reaction? E NaOH H20 (dehydration) A C 3. D. BWhat 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.3. Ethyl phenylacetate (C,HSCH2CO,CH;CH3) is a naturally occurring ester in honey. What hydrolysis products are formed when this ester is treated with water and sulfuric acid (H2SO4)? 4. How could you prepare the following amides using an acid chloride and an amine or ammonia? (a) CH3CH2CONHCH3 (b) N,N-Diethylbenzamide (c) Propanamide
- Propose a structure for an amine with molecular formula CGH7N by interpreting the given 'H and 13C NMR data below. 1H NMR O 2.35 ppm O7.10 ppm 8 8.46 ppm singlet (3) doublet (2) doublet (2) 13C NMR 2, 4 1,5 6.00- 5.00- 4.00- 3.00- 2.00- 1.00- 0.00- 200 120 100 8/ ppm 180 160 140 80 60 40 20Which of the following reactant(s) would be expected to form butan-1-amine as the major product upon reduction with H2, Pd-C? .CN N3 `N3 `CN II II IV III, IV Il only II, IV I, II IV onlyShow how to synthesize the following amines from the indicated starting materials below. Each of the final products may require several sequential steps. Draw the structure for each of the steps and show the reagents required. Starting material Final product h) 4-ethyl-3-methylhexan-1-ol 4-ethyl-3-methylhexan-1-amine i) 2-phenylacetyl chloride N-N-dimethyl-2-phenylethan-1-amine j) ethyl acetate N-ethylpropan-2-amine
- Draw the major organic products of Hofmann elimination from the following amine. CH3 -N HHydrolysis of amides is an important reaction, because it represents the first step in the digestion of dietary protein. Which of the following compounds is formed as a result of the hydrolysis of N,N-diethylpropanamide as shown below? CH3CH2 N-CH2CH3 + H₂O CH2CH3 HCI OA) B) CH3CH2 NH2 HO N-CH2CH3 CH2CH3 H CH3CH2 NHCH2CH3 D)The two most general amine syntheses are the reductive amination of carbonyl compounds and the reduction of amides.Show how these techniques can be used to accomplish the following syntheses.(a) benzoic acid S benzylamine (b) benzaldehyde S benzylamine(c) pyrrolidine S N@ethylpyrrolidine (d) cyclohexanone S N@cyclohexylpyrrolidine(e) HOOC¬(CH2)3 ¬COOH S pentane@1,5@diamine (cadaverine)
