Download Homework #7, Graded Answers

Homework #7, Graded Answers
Chem21, Introduction to Organic and Biochemistry
3.) Assign IUPAC names to the following alcohols.
a.) 1-propanol
b.) 3-phenyl-1-propanol
c.) 2-chloro-3-methyl-1-butanol
d.) 1,4-butanediol
e.) 2-chloro-5-ethylcyclopentanol
f.) 1,2,4-cyclohexanetriol
19.) Which member of each of the following pairs would you expect to be more soluble in
water? Briefly explain your choices.
a.) 2-butanol: has hydrogen bonding and is polar
b.) 2-propanol: smaller size (less nonpolar area)
c.) 2,3-butanediol: has two places to hydrogen bond and add polarity
23.) Draw the structures of the chief product formed when the following alcohols are
dehydrated to alkenes:
a.)
b.)
29.) Write an equation for each reaction.
a.) 1-butanol is heated to 140°C in the presence of sulfuric acid
H2SO4
OH
O
o
140 C
b.) 1-butanol is subjected to an excess of oxidizing agent
[O]
OH
OH
O
c.) 2-pentanol is subjected to controlled oxidation
OH
[O]
O
d.) 2-pentanol is heated to 180°C in the presence of sulfuric acid
OH
H2SO4
o
180 C
e.) 2-methyl-2-pentanol is subjected to oxidation
No reaction  tertiary alcohols do not oxidize
31.) Each of the following conversions requires more than one step. Show the reagents you
would use and draw structural formulas for intermediate compounds formed in each
conversion.
O
a.)
+
H2O
H2SO4
H2SO4
OH
+
OH
o
O
140 C
O
b.)
+
H2O
[O]
H2SO4
O
OH
OH
OH
c.)
OH
H2SO4
OH
+
o
H2O
H2SO4
180 C
d.)
OH
Cl
H2SO4
OH
+
HCl
o
180 C
Cl