Chem 212
Quiz 5a
p.1
NAME__________________________________
Reactions of Alcohols and Thiols (20 pts)
1. (12 pts) Draw the structure of the major organic product(s) for the following reactions:
HO
K2Cr 2O 7
H3C
CH3
H3C
OH
H3C
H2SO 4
K2Cr 2O 7
H2SO 4
OH
K2Cr 2O 7
H2SO 4
SH
oxidation
S
reduction
S
OH
H2O, H 2SO 4
H3C
CH3
2. (4 pts) Show how to prepare 1,2-dibromo-1-methylcyclopentane from 1-methylcyclopentanol.
3. (2 pts) 1,4-Butanediol, hexane, and 1-pentanol have similar molecular weights. Their boiling
points, arranged from lowest to highest, are 69ºC, 138ºC, and 230ºC. Which compound has
which boiling point?
4. (2 pts) Circle the structures below that will react with NaOH:
SH
OH
OH