Conversion of Alcohol to Halide Using H-X (Review Chapter 6)

• Acid Catalyzed

• SN1 Reaction (for all but primary alcohols and Methanol)

• SN2 For Primary Alcohols and Methanol

• Net Reaction

  • CH3CH(OH)CH3 + HX ---> CH3CH(X)CH3

• Reaction Mechanism

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Net Reaction

R-OH + H-X ----> R-X + H2O

Reaction Mechanism(SN1)

1. R-OH + H-X---> R-O+H2 + Cl-

2. R-O+H2 ---> R+ + H2O

3. R+ + Cl- ----> R-Cl

Reaction Mechanism (SN2)

1. R-OH + H-X ---> R-O+H2

2. R-O+H2 + X- ---> R-X + H2O

Transp 138 -Mechanism

Problems 10.16 and 10.17