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  • Chem 212 - Sn2

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    This document provides instructions for a multi-step experiment to synthesize an ionic liquid via an SN2 reaction. The reaction involves nucleophilic substitution between 1-methylimidazole and 1-bromobutane to form 1-butyl-3-methylimidazolium bromide. This intermediate product will then be reacted with potassium hexafluorophosphate to form the final ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate. The document outlines the reaction steps, workup including extraction and drying, characterization including distillation and percent yield calculation, safety considerations, and proper waste disposal procedures.

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    sn2 lab pre lecture

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    This document provides instructions for a multi-step experiment to synthesize an ionic liquid via an SN2 reaction. The reaction involves nucleophilic substitution between 1-methylimidazole and 1-bromobutane to form 1-butyl-3-methylimidazolium bromide. This intermediate product will then be reacted with potassium hexafluorophosphate to form the final ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate. The document outlines the reaction steps, workup including extraction and drying, characterization including distillation and percent yield calculation, safety considerations, and proper waste disposal procedures.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    66 views13 pages

    Chem 212 - Sn2

    Uploaded by

    krista
    This document provides instructions for a multi-step experiment to synthesize an ionic liquid via an SN2 reaction. The reaction involves nucleophilic substitution between 1-methylimidazole and 1-bromobutane to form 1-butyl-3-methylimidazolium bromide. This intermediate product will then be reacted with potassium hexafluorophosphate to form the final ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate. The document outlines the reaction steps, workup including extraction and drying, characterization including distillation and percent yield calculation, safety considerations, and proper waste disposal procedures.

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    © All Rights Reserved
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    of 13

    PrelabLecture

    SN2(GroupExp#2)
    BACKGROUNDREADING:
    Solomons andFryle Chapter6(Sub/Elim Rxns)
    Techniques Weights/Measures,Reflux,LiquidliquidExtraction,Distillation

    LauraPavelka
    laura.pavelka@mcgill.ca
    CHEM212

    PRELABCYCLE1 SN2

    SN2Reactions
    SN2 Reaction bimolecularnucleophilic substitutionreaction(inRDS)
    - nocarbocationformation,concertedmechanism,
    inversionofstereochemistry

    1 >2 >>>>3
    TRANSITIONSTATE

    PURPOSE:performasubstitutionreactionviaanSN2mechanism
    CHEM212

    PRELABCYCLE1 SN2

    SN2Experiment
    Synthesisof1butyl3methylimidazoliumbromide(2steps):

    IONICLIQUID

    CHEM212

    PRELABCYCLE1 SN2

    IonicLiquids

    IONICLIQUID:saltsthatmeltbelow100C(commonlyliquidsatRT)
    CHEM212*lowvapour pressure,lowcombustibility,highthermalstability*
    PRELABCYCLE1 SN2

    Overview SN2Lab

    PURPOSE: performasubstitutionreactionbetween1methylimidazoleand
    1bromobutane viaanSN2mechanismtoprepareanionicliquid
    CHEM212

    PRELABCYCLE1 SN2

    1.Preparationof[C4mim]Br

    water out
    [C4-mim]Br

    0.2 mL water
    0.2 mL 1-methylimidazole
    0.27 mL bromobutane
    water in

    attach condenser

    cool to room temp

    reflux 1 h
    (sand bath)
    CHEM212

    10 mL RBF

    PRELABCYCLE1 SN2

    2.Preparationof[C4mim]PF6
    PF6

    Br
    N

    + KPF6

    H2O
    15 min

    + KBr

    [C4-mim]PF6

    CHEM212

    PRELABCYCLE1 SN2

    3a.Extraction
    PF6
    N

    N
    [C4-mim]PF6

    CHEM212

    PRELABCYCLE1 SN2

    3b.WashingtheAqueouslayer
    PF6
    N

    N
    [C4-mim]PF6

    CHEM212

    PRELABCYCLE1 SN2

    4.DryingOrganicLayer
    PF6
    N

    filter through MgSO4 plug


    rinse vial 1 mL DCM

    N
    [C4-mim]PF6

    MgSO4 pipet
    plug

    DRIED DCM + ionic liquid

    org layer
    4 mL vial (#2)

    pre-weighed
    10 mL RBF
    CHEM212

    PRELABCYCLE1 SN2

    10

    5.Distillation/Isolation
    PF6
    N

    N
    [C4-mim]PF6

    CHEM212

    PRELABCYCLE1 SN2

    11

    %Yield

    MASS

    CRUDE

    Theoretical

    1.5 g

    3.0g

    TOTALLYFICTICIOUSVALUES

    %YIELD(crude)=masscrude x100%=1.5g x100%=50%


    theoretical
    3.0g

    CHEM212

    PRELABCYCLE1 SN2

    12

    Safety&WasteDisposal
    SpecialSafetyConsiderations:
    1methylimidazole VERYhazardousincaseofskin/eyecontact(weargloves),
    hazardousincaseofinhalation/ingestion.
    Bromobutane Hazardousincaseofskin/eyecontact,inhalation/ingestion.Flammable.
    KPF6 Hazardousincaseofskin/eyecontact,VERYhazardousincaseofinhalation/
    ingestion.
    AvoidexposuretofineKPF6dust.
    Dichloromethane Hazardousincaseofskin/eyecontact,inhalation/ingestion.Toxic.

    WasteDisposal:
    Aqueouslayer,Extraction:
    DCMdistillate:
    IsolatedIonicLiquid:
    Pipettes:

    CHEM212

    Washdownthesinkwithlotsofwater
    Halogenatedorganicwaste
    Collectedinlabeledbottle
    Glasswaste

    PRELABCYCLE1 SN2

    13

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