Chapter 9
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
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
9-7
(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
9-10
(a)
1-Pentyne + CH3I, or propyne + CH3CH2CH2I
(b)
3-Methyl-1-butyne + CH3CH2I
(c)
Cyclohexylacetylene + CH3I
Problem
9-12
(b)
1. H2, Lindlar catalyst; 2. O3; 3. Zn CH3CO2H
(c)
1. H2/Lindlar; 2. HBr
(d)
1. H2/Lindlar; 2. BH3; 3. NaOH, H2O2
(e)
1. H2/Lindlar; 2. Cl2
Problem
9-13
(a)
1. HCCH + NaNH2 ; 2. CH3(CH2)6CH2Br; 3. 2 H2/Pd
(b)
HCCH + NaNH2 ; 2. (CH3)3CCH2CH2I; 3. 2 H2/Pd
(c)
1. HCCH + NaNH2 ; 2. CH3CH2CH2CH2I; 3. BH3; 4. H2O2
(d)
1. HCCH + NaNH2 ; 2. CH3CH2CH2CH2CH2I; 3. HgSO4, H3O+