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192 Chapter 5
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b.
+
Br
Br
+
+
electrophile
nucleophile
c.
H
electrophile
nucleophile
C
O
CH
3
O
HO
H
2
O +
+
C
CH
3
O
O
−
−
d.
CH
3
C Cl
CH
3
CH
3
C
CH
3
+
+
CH
3
CH
3
electrophile nucleophile
Cl
−
16.
The labels are under the structures in Problem 15.
17.
1.
C
O
Br
CH
3
CH
3
C
O
CH
3
CH
3
+
Br
−
2−
+
O H
H
CH
3
O CH
3
+
H
+
−
H
+
2
Drawing the arrows incorrectly leads to a bromine with an incomplete octet and a positive
charge as well as an oxygen with 10 valence electrons and 2
−
charge.
Drawing the arrows incorrectly leads to an oxygen with an incomplete octet and a 2+ charge.
2.
This one cannot be drawn because the arrow is supposed to show where the electrons move to, but
there are no electrons on the H to go anywhere.
3.
CH
3
COCH
3
O
+
HO
−
?
The product cannot be drawn because the destination of the electrons in the breaking
π
bond is
not clear.
4.
This one cannot be drawn because the arrow is supposed to show where the electrons move to, but
there are no electrons on the C to go anywhere.