tb24 - Chaoter 24 - Amines and Heterocvcles ClassifY each...

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Chaoter 24 - Amines and Heterocvcles ClassifY each of the following nitrogen atoms in the following compounds as primary, secondary, tertiary, or quaternary . CH3 I 1. H0 6 CHCHNHCH3 : I 'P'''"'' Answer: The nitrogen atom in ephedrine is secondary. 2. < > CH'rCH, NH2 amphetamine Answer: The nitrogen atom in amphetamine is primary. 3. 0 mepiquat chloride + ..- N :CI: /\ .. H3C CH3 Answer: The nitrogen in mepiquat chloride is a quaternary ammonium salt. CH3 4. OH fexofenadine Answer: The nitrogen atom in fexofenadine is tertiary Draw structures corresponding to each of the following names: 5. diisopropylamine Answer: H I iNy Test Items for McMurry's Organic Chemistry, Seventh Edition ~H 271
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6. N;N-dimethylcyclopentanamine Answer: "'-N~CH3 V- CH3 7. 1,4-butanediamine Answer: H2NCH2CH2CH2CH2NH2 8. p-methoxyaniline Answer: H,m-Q- NH, Name each of the following compounds by IUPAC rules. CH3 I 9. ONb;:CH' Answer: N-isopropyll-N-methylcyclobutylamine 10. U H2N . NH2 Answer: 2,4-hexanediamine 0 11. ~OCH' NH2 Answer: methyl 2-aminobutanoate 12. < > NHCH,CI1, Answer: N-ethylaniline 272 Chapter 24: Amines and Heterocycles
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13. Cl QN'ffi3 I CH3 Answer: m-chloro-N,N-dimethylaniline 14. O,N-0-NH2 Answer: p-nitroaniline Consider the reaction below to answer the following questions. Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H2/Ni. UY [Ul,] H2/Ni. . ~ V NHCH3 CH3NH2 .. A 15. Identify the nucleophile in the initial reaction of phenyl-2-propanone to yield intermediate A. Answer: The nucleophile is methylamine. 16. Intermediate A is an example of: a. b. c. d. an imine an enamine an iminium ion an imide Answer: a 17. Although the yield of methamphetamine is good, some unreacted phenyl-2-propanone remains after the reaction is complete. Describe how methamphetamine can be separated from phenyl-2-propanone. Answer: Dissolve the reaction mixture containing the ketone and amine in ether and extract with aqueous HC!. The basic amine will dissolve in the aqueous layer as its hydrochloric salt. The neutral ketone will remain in the ether layer. Separate the two layers and neutralize the aqueous layer with NaOH. Extract the neutralized layer with ether. The purified amine will dissolve in the ether. Test Items for McMurry's Organic Chemistry, Seventh Edition 273
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Refer to the Table of pKa s below to answer the following questions: pKas of Some Arylammonium Ions y-o-~] y -H -C=N -NHz pKa 4.63 1.74 6.15 18. Based on the pKa s for their corresponding ammonium ions, which aryl amine above is the strongest base? Answer: p-aminoaniline 19. Explain the difference in acidity between p-cyanoanilinium ion and anilinium ion. Use both words and structures.
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This note was uploaded on 10/10/2011 for the course CHEMISTRY CHM2046 taught by Professor Johnston during the Spring '11 term at University of South Florida - Tampa.

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tb24 - Chaoter 24 - Amines and Heterocvcles ClassifY each...

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