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15.5.9: Chapter 9

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    482463
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    Problem 9-1
    (a) 2,5-Dimethyl-3-hexyne
    (b) 3,3-Dimethyl-1-butyne
    (c) 3,3-Dimethyl-4-octyne
    (d) 2,5,5-Trimethyl-3-heptyne
    (e) 2,4-Octadiene-6-yne
    Problem 9-2 1-Hexyne, 2-hexyne, 3-hexyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 4-methyl-2-pentyne, 3,3-dimethyl-1-butyne
    Problem 9-3
    (a) 1,1,2,2-Tetrachloropentane
    (b) 1-Bromo-1-cyclopentylethylene
    (c) 2-Bromo-2-heptene and 3-bromo-2-heptene
    Problem 9-4
    (a) 4-Octanone
    (b) 2-Methyl-4-octanone and 7-methyl-4-octanone
    Problem 9-5
    (a) 1-Pentyne
    (b) 2-Pentyne
    Problem 9-6
    (a) C6H5C   CH
    (b) 2,5-Dimethyl-3-hexyne
    Problem 9-7
    (a) Mercuric sulfate–catalyzed hydration of phenylacetylene
    (b) Hydroboration/oxidation of cyclopentylacetylene
    Problem 9-8
    (a) Reduce 2-octyne with Li/NH3.
    (b) Reduce 3-heptyne with H2/Lindlar catalyst.
    (c) Reduce 3-methyl-1-pentyne.
    Problem 9-9 No: (a), (c), (d); yes: (b)
    Problem 9-10
    (a) 1-Pentyne + CH3I, or propyne + CH3CH2CH2I
    (b) 3-Methyl-1-butyne + CH3CH2I
    (c) Cyclohexylacetylene + CH3I
    Problem 9-12
    (a) KMnO4, H3O+
    (b) H2/Lindlar
    (c) 1. H2/Lindlar; 2. HBr
    (d) 1. H2/Lindlar; 2. BH3; 3. NaOH, H2O2
    (e) 1. H2/Lindlar; 2. Cl2
    (f) O3
    Problem 9-13
    (a) 1. HC CH + NaNH2 ; 2. CH3(CH2)6CH2Br; 3. 2 H2/Pd
    (b) HC CH + NaNH2 ; 2. (CH3)3CCH2CH2I; 3. 2 H2/Pd
    (c) 1. HC CH + NaNH2 ; 2. CH3CH2CH2CH2I; 3. BH3; 4. H2O2
    (d) 1. HC CH + NaNH2 ; 2. CH3CH2CH2CH2CH2I; 3. HgSO4, H3O+

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