51C Practice Problems 5
Spring 2016
1. Predict the products or provide reagents in the following reactions. For reactions that require
reagents, if more than one step is required, number individual steps.
O
a.
H2O
18OCH CH
2
3
CH3
H3O+
2 products (show where label is!)
O
OH
b.
H3C
CH3
Cl
pyridine
O
H3C
Br
H3C
c.
NEt2
DEET (the active ingredient
in Off insect repellant)
O
d.
CH3CH2
O
NH2
CH3CH2
Cl
2. Provide a mechanism for the following reaction, which we used back in chapter 18 to convert
aniline (a highly activated aromatic ring) into acetanilide (a moderately activated aromatic ring.)
O
O
NH2
H3C
HN
Cl
pyridine
CH3
3. Provide mechanisms for the following two reactions:
O
a.
CH3
C
O
Na18OH
H218O
OCH3
O
b.
HO
CH3
C
18O!
H3O+
OH
+
CH3OH
O
H2O
O
4. Sulfonate esters react with thionyl chloride to form sulfonyl chlorides. This is analogous to the
reaction of carboxylic acids with thionyl chloride. With this reaction in mind, show how to
synthesize tosyl chloride starting from benzene:
O
R S OH
O
SOCl2
R S Cl
O
O
?
O
H3C
S Cl
O
Toluenesulfonyl chloride
(Tosyl chloride)