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2H2O H3O+ Br
_
Br
+
+


HS -

BF3

(CH3)3N

CH2
I > II > III > IV

II > I > III > IV


NH3

H2O

CH3COOH
NO2ˉ

CNˉ

NaHSO3

Clˉ
CF3SO3ˉ > CCl3SO3ˉ
CNˉ > Iˉ

NH2ˉ > OHˉ


(CH3)3CLi

NaNH2

CH3ONa

NaOH
CH3Oˉ > CH3ˉ

CH3Sˉ > CH3SH

NH3 > H2O

(CH3CH2)3N > (CH3CH2)3P


⇌ Br
_
Narrow
opening
(RDS)

Large
openings
Narrow opening
(RDS)

Largest
opening

Large
opening
Narrow opening
(RDS)

Large
opening

Largest
opening
Large
opening

Narrow
opening
(RDS)

Large
opening
Br Nu-
Nu
R2
C C
C R1 R3
R3 R1 R3 R1
R2 R2
Br R2
R2
R3 R1
C C R1 C
R3
R3 R1
Nu
R2 Nu-
Nu R2

C R3 R1
R3 C
R1
R2
Nu
CH3 CH3

H3C C CH2 Br H3C C OCH3

H CH3
CH3 CH3 CH3

H2 O
H C Cl H C OH + HO C H
AgNO3

C2H5 C2H5 C2H5


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