Preparation of t-butyl chloride - University of Illinois Archives...Preparation of t-butyl chloride (2-chloro-2-methylpropane) C CH3 CH3 CH3 OH HCl C CH3 CH3 CH3 Cl + H2O t-butyl alcohol

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  • Preparation of t-butyl chloride(2-chloro-2-methylpropane)

    CCH3

    CH3CH3

    OHHCl

    CCH3

    CH3CH3

    Cl + H2O

    t-butyl alcohol t-butyl chloride

  • (CH3)3COH + HCl

    (CH3)3CCl + H2O

    Reaction Mechanism?

  • (CH3)3COH + H-Cl

    (CH3)3COH2 + Cl + -

    Leaving Group

  • (CH3)3C-OH2 +

    (CH3)3C + H2O

    Cation

  • (CH3)3C + + Cl

    -

    (CH3)3CCl

  • C CH3CH3

    CH3

    tert-Butyl Cation

    +sp2 flat

    p

  • 2

    Transition State

  • Substitution

    Nucleophilic

    1 bondat a time

  • Increasing Stability

  • Main Reaction

    Side Reaction

    CCH3

    CH3CH3

    OHHCl

    CCH3

    CH3CH3

    Cl + H2O

    t-butyl alcohol t-butyl chloride

    CCH3

    CH3CH3

    OHHCl

    + H2O

    t-butyl alcohol

    CH2CCH3

    CH3

    isobutylene

  • CH2CCH3

    CH3

    C

    CH3

    CH3CH3

    CCH3

    CH3CH3

    Cl

    E1 N

  • ProcedureShake t-BuOH with concentrated HCl

    Separate layers

    Wash saturated aqueous NaCl

    Wash saturated aqueous NaHCO3

    Dry

    Distill

  • t-BuCl

    Shake t-BuOH with HCl

  • NaHCO3 + HCl

    CO2 + H2O + NaCl

    Wash to remove excess HCl

  • Distill product

    Cool receiver

  • Clamp joints

  • Yield Calculations

    A + B CMW 100 100 200

    Use: 10 g A 20 g B

    Limiting Reagent

    Theoretical Yield

    Experimental Yield

  • A + B CMW 100 100 200

    Cpd Mass MW Moles

    A 10 g 100 0.10

    B 20 g 100 0.20

    Theoretical yield:0.10 moles x 200 = 20 g

    Experimental yield (%):100 x wt product / 20

    LimitingReagent

  • CH3CH2CH2CH2OH n-butyl alcohol

    HBr

    CH3CH2CH2CH2Brn-butyl bromide

  • RCH2OH + H+ RCH2OH2+

    C

    R

    HHOH2Br

    +

    transition state

    RCH2Br

  • Substitution

    Nucleophilic

    2 bonds ata time