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32.5.22: Chapter 22

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    487225
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    (b) An alkene in which C 1 is bonded to a hydroxyl group on top and methyl sulfide group on the right.
    (c) An alkene in which C 1 has two hydrogen atoms on it and C 2 is linked to a  hydroxyl group and to an oxygen which in turn is linked to an ethyl group.
    (d) An alkene in which C 1 has two hydrogen atoms on it and C 2 is linked to a  hydroxyl group and to a hydrogen atom
    (e) An alkene in which C 1 has two hydrogen atoms on it and C 2 is linked to two  hydroxyl groups.
    (f) Two alkene structures. C 2 is bonded to hydroxyl and methyl groups but in second structure, C 2 is bonded to hydroxyl and C H 2 P h.
    Problem 22-2 (a) 4 (b) 3 (c) 3 (d) 2 (e) 4 (f) 5
    Problem 22-4 Acid-catalyzed formation of an enol is followed by deuteronation of the enol double bond and dedeuteronation of oxygen.
    Problem 22-5 1. Br2; 2. Pyridine, heat
    Problem 22-6 The intermediate α-bromo acid bromide undergoes a nucleophilic acyl substitution reaction with methanol to give an α-bromo ester.
    Problem 22-7
    (a) CH3CH2CHO
    (b) (CH3)3CCOCH3
    (c) CH3CO2H
    (d) PhCONH2
    (e) CH3CH2CH2CN
    (f) CH3CON(CH3)2
    Problem 22-9 Acid is regenerated, but base is used stoichiometrically.
    Problem 22-10
    (a) 1. Na+ −OEt; 2. PhCH2Br; 3. H3O+
    (b) 1. Na+ −OEt; 2. CH3CH2CH2Br; 3. Na+ −OEt; 4. CH3Br; 5. H3O+
    (c) 1. Na+ −OEt; 2. (CH3)2CHCH2Br; 3. H3O+
    Problem 22-11 Malonic ester has only two acidic hydrogens to be replaced.
    Problem 22-12 1. Na+ −OEt; 2. (CH3)2CHCH2Br; 3. Na+ −OEt; 4. CH3Br; 5. H3O+
    Problem 22-13
    (a) (CH3)2CHCH2Br
    (b) PhCH2CH2Br
    Problem 22-14 None can be prepared.
    Problem 22-15 1. 2 Na+ −OEt; 2. BrCH2CH2CH2CH2Br; 3. H3O+
    Problem 22-16
    (a) Alkylate phenylacetone with CH3I
    (b) Alkylate pentanenitrile with CH3CH2I
    (c) Alkylate cyclohexanone with H2C CHCH2Br
    (d) Alkylate cyclohexanone with excess CH3I
    (e) Alkylate C6H5COCH2CH3 with CH3I
    (f) Alkylate methyl 3-methylbutanoate with CH3CH2I

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