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    Chapter 7 Elimination Reactions: I. Unimolecular Elimination, E1

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    Roberto SIlva
    1. Chapter 7 discusses elimination reactions where a leaving group and hydrogen are removed from a carbon, forming a double bond (E1 and E2). 2. E1 reactions are stepwise and involve the formation of a carbocation intermediate. E2 reactions are concerted and do not involve a carbocation. 3. Whether a substitution or elimination reaction occurs depends on factors like the nucleophile strength/basicity and the substrate structure - stronger bases and more sterically hindered substrates favor elimination.

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    Chapter 7 Elimination Reactions: I. Unimolecular Elimination, E1

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    Roberto SIlva
    31 views8 pages
    1. Chapter 7 discusses elimination reactions where a leaving group and hydrogen are removed from a carbon, forming a double bond (E1 and E2). 2. E1 reactions are stepwise and involve the formation of a carbocation intermediate. E2 reactions are concerted and do not involve a carbocation. 3. Whether a substitution or elimination reaction occurs depends on factors like the nucleophile strength/basicity and the substrate structure - stronger bases and more sterically hindered substrates favor elimination.

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    Organic Chemistry II

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    1. Chapter 7 discusses elimination reactions where a leaving group and hydrogen are removed from a carbon, forming a double bond (E1 and E2). 2. E1 reactions are stepwise and involve the formation of a carbocation intermediate. E2 reactions are concerted and do not involve a carbocation. 3. Whether a substitution or elimination reaction occurs depends on factors like the nucleophile strength/basicity and the substrate structure - stronger bases and more sterically hindered substrates favor elimination.

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    Download as ppt, pdf, or txt
    31 views8 pages

    Chapter 7 Elimination Reactions: I. Unimolecular Elimination, E1

    Uploaded by

    Roberto SIlva
    1. Chapter 7 discusses elimination reactions where a leaving group and hydrogen are removed from a carbon, forming a double bond (E1 and E2). 2. E1 reactions are stepwise and involve the formation of a carbocation intermediate. E2 reactions are concerted and do not involve a carbocation. 3. Whether a substitution or elimination reaction occurs depends on factors like the nucleophile strength/basicity and the substrate structure - stronger bases and more sterically hindered substrates favor elimination.

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    Chapter 7 Elimination Reactions

    I. Unimolecular Elimination, E1
    A. Elimination Reactions
    1) Removal of L.G. and H, but no substitution
    2) Formation of a C==C double bond
    H R B- R R
    R
    + BH + X -
    R R R
    R X
    B. Solvolysis of 2-bromo-2-methylpropane actually gives 2 products
    H2O - +
    Br OH + + Br + H
    SN1 E1
    1) Rate of reaction for both products = k[haloalkane] E1
    2) E1 Mechanism
    a) Step 1 is Dissociation (just like for SN1)

    Br
    b) Step 2 is Deprotonation to form the Alkene

    CH2 H CH2
    = CH3 C CH3 C + H3O+
    + H2O
    CH3 CH3
    C. E1 can give a mixture of products because any H can be removed
    H CH3 H H CH3 H
    H2O
    Et C CH3 Et C CH3
    SN1 Product
    Et Br CH3 Et OH CH3

    CH2
    H H H CH3 CH3 CH3 H
    Et
    Et C CH3 + Et C + C CH3
    Et CH3 Et Br CH3 Et Br CH3

    E1 Products
    II. Bimolecular Elimination, E2
    A. Strong Bases affect nucleophilic substitution reactions (OH- and RO-)
    1) Rate = [B-][RX] (second order or bimolecular)
    2) Must occur before a carbocation forms, or we would just have SN1, E1

    B. E2 Mechanism
    1) Occurs in a single, concerted step
    2) Must have strong base
    3) Mechanism

    HO- H R R R
    R
    + OH2 + X -
    R R R
    R X
    4) Orbital Picture
    C. Comparison of E1 and E2
    1) E1 is stepwise and involves a carbocation

    CH2 H CH2
    Br CH3 C
    + H2O CH3 C + H3O+
    CH3 CH3

    2) E2 is concerted

    HO- H R R R
    R
    + OH2 + X -
    R R R
    R X

    D. Experimental Evidence for Concerted E2 Mechanism


    1) Second order rate law shows base and RX involved in R.D.S.
    2) Better L.G. is faster (Bond breaking is important in R.D.S.)
    3) Stereochemistry is important
    a) If anti Hydrogen is present, E2 is fast
    b) If anti Hydrogen is not present E2 is very slow
    Br

    fast slow Br
    H - H
    CH3O- CH3O
    H H
    III. Substitution and Elimination
    A. SN2, SN1, E2, E1 all occur from RX + Nu

    B. How do we predict what the reaction will produce?


    1) Weakly basic strong nucleophiles give substitution products
    a) Good Nucleophiles
    b) Base weaker than OH-
    c) I-, Br-, RS-, N3-, RCO2-, PR3, CN-
    d) SN2 for primary and secondary RX
    e) SN1 for tertiary RX
    2) Weakly basic weak nucleophiles can only do SN1/E1 (H2O, ROH)
    CH2
    CH3 H2O
    Br CH3 C CH3 C + OH
    CH3 CH3
    3) Strongly basic Nu’s give more E as Bulk increases (OH-, RO-, NH2-)
    -
    HO- + Br OH + Br SN2 mostly

    - - E2 mostly
    HO + Br + Br

    HO:- + Br + Br- E2 mostly


    -
    4) Sterically hindered bases favor Elimination O
    a) Too bulky to do substitution
    b) E2 or E1 depending on RX

    O- -
    + Br + Br

    C. Reactivity of Haloalkanes
    1) Primary Haloalkanes
    a) SN2 mostly, can be slowed by bulk at C2 X
    b) E2 only if Bulky base

    2) Secondary Haloalkanes
    a) SN2 with good nucleophiles, weak base, Polar Aprotic Solvent
    b) SN1/E1 with good LG, weak Nu, Polar Protic Solvent
    c) E2 with strong base, Polar Protic Solvent

    3) Tertiary Haloalkane
    a) SN1/E1 with good LG, no base (solvolysis)
    b) E2 with strong base

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