Chemistry Exam Worksheet - Chemistry 61, Dr. M.t. Crimmins, The University Of North Carolina At Chapel Hill Page 5

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24.
+
H
CH
CH
3
3
excess HBr
O H
Br
C
CH
O
C
CH
3
3
+
CH
CH
3
3
why is this not converted to the bromide? C–O bond too strong, and
vinyl cation too unstable
H
CH
H
3
CH
+
3
O
C
CH
O
3
+
+ C
CH
–
3
Br
CH
3
CH
3
25.
H
C
CH
HBr
H
C
Br
3
3
3
+
C C
H
C C C CH
C C
3
3
H
Br
H
CH
3
+
–
H
Br
–
Br
H
C C
C CH
3
3
+
H
–
Br
– 5 –

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