Chem 334 - Summer 1998 - Organic Chemistry I
Dr. Carl C. Wamser Dr. Carl C. WamserVollhardt & Schore, pp 270 - 276
Problems 1 , 2 , 3 , 4 , 8 , 9 , 10 , 11 , 12 , 14 , 19 , 22 , 27 , 28
1. Arrange the following in order of decreasing acidity:
H2O , H3O+ , H2SO4 , NH3 , CH4 , CH3OH , CH3CH2OH , 1-methylcyclohexanol , 2-methylcyclohexanol
(See Tables 6.5 and 8.2)
2. Arrange the following in order of decreasing basicity:
H2O , OH- , NH3 , NH2- , CH4 , CH3- , CH3O- , CH3CH2O- , iPrO- , tBuO-
3. Write four different syntheses for 2-methyl-2-hexanol, beginning with compounds having five or fewer carbon atoms.
Estimate which is most likely to be the preferred laboratory synthesis.
4. Write synthetic sequences for the compounds below, using as the only organic starting materials alcohols having five carbons or less, plus any needed solvents or inorganic reagents.
a) 3-ethyl-2-methyloctan-2-ol
b) 3,4-diethyl-1-hexanol
