In the following pairs of nucleophilic substitution reactions, which one has a higher reaction rate? Explain why.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter12: Infrared Spectroscopy
Section12.3: Infrared Spectroscopy
Problem 12.1P
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In the following pairs of nucleophilic substitution reactions, which one has a higher reaction rate? Explain why.

(а)
not
H20
+
Br
HBr
+
HOT
SN1
Br
OH
H20
HBr
+
SN1
+
Transcribed Image Text:(а) not H20 + Br HBr + HOT SN1 Br OH H20 HBr + SN1 +
(b)
+ CH3NH2
SN2
H2
+ CH3NH2
ONH2 cí
SN2
(c)
H20
Br
+
NaSH
SH
+
NaBr
SN2
H20
NaOH
HO.
NaBr
+
+
Br
SN2
(d)
CH3OH
NaSH
NaBr
Br
+
SH
+
SN2
„Me
Me
Br
+
NaSH
SN2
SH
+
NaBr
Transcribed Image Text:(b) + CH3NH2 SN2 H2 + CH3NH2 ONH2 cí SN2 (c) H20 Br + NaSH SH + NaBr SN2 H20 NaOH HO. NaBr + + Br SN2 (d) CH3OH NaSH NaBr Br + SH + SN2 „Me Me Br + NaSH SN2 SH + NaBr
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