Practice_Ch 17-1
1. Rank the labeled hydrogens in the following compound in order of increasing the acidity
(least to most)
O
OH
CH
2
CH
2
H
a b c d
2. List the following compounds in order of decreasing pKa value of their α-hydrogens (least
acidic to most acidic):
2,4-pentanedione, diethyl malonate, propanal, ethyl acetate.
3. Complete the following reactions. If the reaction does not occur, put NR.
a.
O
H
3
O
+
xs Br
2
?
b.
O
HO
-
xs Br
2
?
c.
O1, H
3
O
+
, Br
2
2. HO
-
, heat
?
d.
1, PBr
3
, Br
2
2. H
3
O
+
?
OH
O
e.
CH3I?
N
f.
1. LDA, -75
o
C
?
O
Cl
O
2.
g.
EtO
O
H
O1. LDA
2. CH
3
CH
2
I
?NaBH
4
CH
3
OH ?
h.
?1.
2. HCl, H
2
O
?
ONH
O
