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24.E: Amines and Heterocycles (Exercises)

  • Page ID
    61707
  • These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry textbook.

    24.3 Basicity of Amines

    24.3 Exercises

    Questions

    Q24.3.1

    Select the more basic amine from each of the following pairs of compounds.

    (a)

    (b)

    (c)

    Q24.3.2

    The 4-methylbenzylammonium ion has a pKa of 9.51, and the butylammonium ion has a pKa of 10.59. Which is more basic? What's the pKb for each compound?

    Solutions

    S24.3.1

    (a)

    (b)

    (c)

    S24.3.2

    The butylammonium is more basic. The pKb for butylammonium is 3.41, the pKb for 4-methylbenzylammonium is 4.49.

    24.7 Reactions of Amines

    24.7 Exercises

    Questions

    Q24.7.1

    Draw the product for a Hoffman elimination for each of the following molecules.

    (a)

    (b)

    (c)

    (d)

    Q24.7.2

    Draw the product of a Hoffman elimination for the following molecule.

    Solutions

    S24.7.1

    (a)

    (b)

    (c)

    (d)

    S24.7.2

    24.8 Reactions of Arylamines

    24.8 Exercises

    Questions

    Q24.8.1

    Propose a synthesis for the following compound via benzene and any amine you may require.

    Q24.8.2

    Proposes synthesis for each of the following compounds via benzene.

    (a) N,N-Diethylaniline

    (b) p-Bromoaniline

    (c) m-Bromoaniline

    (d) 2,4-Diethylaniline

    Q24.8.3

    Propose a synthesis for each of the following molecules from benzene via the diazonium ion.

    (a) p-Chlorobenzoic acid

    (b) m-Chlorobenzoic acid

    (c) m-Dichlorobenzene

    (d) p-Ethylbenzoic acid

    (e) 1,2,4-Trichlorobenzene

    Solutions

    S24.8.1

    S24.8.2

    (a) 1. HNO3, H2SO4; 2. Zn(Hg), HCl; 3. EtBr

    (b) 1. HNO3, H2SO4; 2. Zn(Hg), HCl; 3. (CH3CO)O2; 4. Br2, FeBr3; 5. H2O, NaOH

    (c) 1. HNO3, H2SO4; 2. Br2, FeBr3; 3. Zn(Hg), HCl

    (d) 1. HNO3, H2SO4; 2. Zn(Hg), HCl; 3. (CH3CO)O2; 4. EtCl, AlCl3; 5. H2O, NaOH

    S24.8.3

    (a) 1. CH3CH2Cl, AlCl3; 2. HNO3, H2SO4; 3. SnCl2; 4. NaNO2, H2SO4; 5. CuBr; 6. KMnO4, H2O

    (b) 1. HNO3, H2SO4; 2. Cl2, FeCl3; 3. SnCl2, H3O+; 4. NaNO2, H2SO4; 5. CuCN; 6. H3O+

    (c) 1. HNO3, H2SO4; 2. Cl2, FeCl3; 3. SnCl2; 4. NaNO2, H2SO4; 5. CuCl

    (d) 1. CH3CH2Cl, AlCl3: 2. HNO3, H2SO4; 3. SnCl2; 4. NaNO2, H2SO4; 5. CuCN; 6. H3O+

    (e) 1. HNO3, H2SO4; 2. H2/PtO2; 3. (CH3CO)2O; 4. 2 Cl2; 5. H2O, NaOH; 6. NaNO2, H2SO4; 7. CuCl

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