Chem 2124 Amine practice problems1. Draw the structure of the following compounds. a. pyridine N b. piperidine N H c. o-toluidine CH3 NH2 d. 2,3-dimethyl-2-butanamine NH2 2. Give an acceptable name for each of the following compounds. N CH3 4 CH3 N,N-dimethylbenzylamine N Cl- tetrabutylammonium chloide 3. How might the presence of an N–H functionally be indicated using NMR spectroscopy? The N-H hydrogen can be exchanged with deuterium by simply adding D2O to the sample. This will cause the N-H signal to disappear from the 1H NMR spectra. O CH3 C Cl + H2NCH2CH2CH3 O CH3 C Cl H N CH2CH2CH3 H O CH3 C H + Cl H N CH2CH2CH3 O CH3 C H N CH2CH2CH3 + HCl 6. Complete the following reaction sequences. 1) Ag2O 2) heat N CH3 CH3 3) CH3I 4) Ag2O 5) heat b. stepwise mechanism for the reaction of acetyl chloride with n-propylamine. a. Circle the stronger base in the pair below. and briefly explain your choice. NH2 NH2 The lone pair of electrons on the nitrogen in aniline are delocalized into the aromatic ring. Provide a detailed. 5. NH2 CH3I (excess) NaHCO3 N(CH3)3 I . which reduced the ability of aniline to donate electron (be a base).4. + HBr N N H + Br . O2N Br f. CH H 3 e. O CN h.c. O Cl CH3CH2NH2 NaHCO3 O NCH2CH3 H d. H NH2 g. acetone / H lose of water 1) LAH 2) pH adjust H N NH2 N m. Give an efficient method for preparing 1-pentanamine from 1-butene. Cl xs NH3 NH2 . Give an efficient method for preparing ethylisopropylamine from ethylamine. Devise an efficient method for preparing only 1-pentanamine from 1-chloropentane. O Cl 1) CH3NH2 O NHCH3 2) LiAlH4 3) H2O NHCH3 k. HBr peroxide Br NaCN acetone 1) LAH CN 2) pH adjust NH2 l. H3C N CH3 H2O2 H3C O N CH3 j.i. n. O H + O H H H2NCH3 H O H NHCH3 H Base CH3 N H H O H NHCH3 H O H NHCH3 Base N CH3 The base is either the amine or water. NH2 1) NaNO2 / HCl 2) CuCN 3) LAH NH2 7. Circle the following amines that could be formed by reduction of an amide? 1) benzylamine 2) isopropylamine 3) aniline 4) triethylamine The answer is #1 and #4. Provide a detailed. . 8. Complete the short synthesis below by providing the necessary reagents. stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine. 9. H N or O The answer is A and B. or NH2 B. 10. O NH2 A. Propose a synthetic route to prepare p-nitroaniline from aniline. NH2 NH2 NO2 O 1) CH3 C Cl / NaHCO3 2) HNO3 / H2SO4 3) H+ / H2O / heat . Circle the most basic compound in each of the following pairs. 11.6 ppm disappears on shaking with D2O.8 ppm indicate symmetrical ethylene groups –CH2CH2-.6 ppm is a N-H. 5H 2H 4H 4H 1H 5 aromatic hydrogens (mono substituted benzene). Isolated CH2 at 3. The peaks at 2. since there is only one hydrogen this is a 2° amine. A compound with the formula C11H16N2 gave the following IR and 1H NMR spectra. Propose a structure for the compound and show how your structure accounts for the observed spectra data. CH2 N NH . The proton at 1.5 ppm attached to aromatic ring and nitrogen. The other nitrogen must be a 3° amine.4 and 2. Peak @ 1.