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    Substitution and Elimination Practice Problems

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    Imran Khan Sulaiman
    This document provides practice problems for substitution and elimination reactions. It lists reaction conditions and reactants, and asks the reader to predict the major organic product and indicate the predominant mechanism - SN1, SN2, E1 or E2. The answers are then provided, correctly identifying the major product structure and mechanism for each reaction based on factors like temperature, the nature of the reactants and leaving groups.

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    © All Rights Reserved
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    Substitution and Elimination Practice Problems

    Uploaded by

    Imran Khan Sulaiman
    280 views2 pages
    This document provides practice problems for substitution and elimination reactions. It lists reaction conditions and reactants, and asks the reader to predict the major organic product and indicate the predominant mechanism - SN1, SN2, E1 or E2. The answers are then provided, correctly identifying the major product structure and mechanism for each reaction based on factors like temperature, the nature of the reactants and leaving groups.

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    This document provides practice problems for substitution and elimination reactions. It lists reaction conditions and reactants, and asks the reader to predict the major organic product and indicate the predominant mechanism - SN1, SN2, E1 or E2. The answers are then provided, correctly identifying the major product structure and mechanism for each reaction based on factors like temperature, the nature of the reactants and leaving groups.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    280 views2 pages

    Substitution and Elimination Practice Problems

    Uploaded by

    Imran Khan Sulaiman
    This document provides practice problems for substitution and elimination reactions. It lists reaction conditions and reactants, and asks the reader to predict the major organic product and indicate the predominant mechanism - SN1, SN2, E1 or E2. The answers are then provided, correctly identifying the major product structure and mechanism for each reaction based on factors like temperature, the nature of the reactants and leaving groups.

    Copyright:

    © All Rights Reserved
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    of 2

    CHM 211

    Substitution and Elimination practice problems

    Analyze the reactant(s) and reaction conditions, then predict the structure of the major organic
    product and indicate the predominant mechanism (SN1, SN2, E1, or E2) of each reaction.

    CH3CH2CH2CH2Br

    CH3CH2CH2CH2Br

    K OC(CH3)3
    (CH3)3COH, 82 C
    Na OCH3
    CH3OH, 0 C

    CH3CH2CH CH2

    E2 (high T,
    good base)

    CH3CH2CH2CH2OCH3

    SN2 (low T,
    good Nu or base)

    Cl
    Na SCH2CH3

    SCH2CH3
    SN2 (low T,
    good Nu)

    DMF, 0 C
    CH3I

    NaNO 2

    CH3
    CH3

    SN2 (low T)

    CH3NO 2
    5 C

    H2O

    C OTs

    22 C

    CH3

    CH3

    C OH
    CH3

    CH3
    Br

    CH3I

    CH3

    CH3OH

    CH3

    22 C

    OCH3

    CH3

    K OC(CH3)3

    Br

    (CH3)3COH, 82 C

    CH3SH

    CH3

    CH3SCH3

    SN1 (low T,
    weak Nu,
    weak base)
    SN1 (low T,
    weak Nu,
    weak base)

    E2, some E1
    (high T, good base)

    SN 2 (low T)

    43 C

    Cl
    Na OCH2CH3
    E2 (high T, good base)

    CH3CH2OH, 78 C
    CH3
    I

    H2O
    22 C

    BrBr

    Na OCH3
    CH3OH, 0 C

    CH3
    OH

    OCH3

    SN 1 (low T,
    weak Nu,
    weak base)

    SN2 (low T,
    allylic RX)

    CHM 211

    Substitution and Elimination practice problem answers

    Analyze the reactant(s) and reaction conditions, then predict the structure of the major organic
    product and indicate the predominant mechanism (SN1, SN2, E1, or E2) of each reaction.
    CH3CH2CH2CH2Br

    CH3CH2CH2CH2Br

    K OC(CH3)3
    (CH3)3COH, 82 C
    Na OCH3
    CH3OH, 0 C

    CH3CH2CH CH2

    E2 (1 RX, high T,
    good base)

    CH3CH2CH2CH2OCH3

    SN2 (1 RX, low T,


    good Nu or base)

    Cl
    Na SCH2CH3

    SCH2CH3
    SN2 (2 RX, low T,
    good Nu)

    DMF, 0 C
    CH3I

    5 C
    CH3

    CH3

    SN2 (Methyl)

    CH3NO2

    NaNO2

    H2O

    C OTs

    22 C

    CH3

    CH3

    C OH
    CH3

    CH3
    Br

    CH3I

    CH3

    CH3OH

    CH3

    22 C

    OCH3

    CH3

    K OC(CH3)3

    Br

    (CH3)3COH, 82 C

    CH3SH

    CH3

    CH3SCH3

    SN1 (3 RX, exc. L


    low T, weak Nu
    weak base)
    SN1 (3 RX, good L
    low T, weak Nu,
    weak base)

    E2, some E1 (3 RX, good


    L, high T, good base)

    SN2 (Methyl)

    43 C

    Cl
    Na OCH2CH3

    E2 (2 RX, high T,
    good base)

    CH3CH2OH, 78 C
    CH3
    I

    H2O
    22 C

    BrBr

    Na OCH3
    CH3OH, 0 C

    CH3
    OH

    OCH33
    OCH

    SN1 (3 RX, low T,


    v. good L, weak
    Nu, weak base)

    SN2 (allylic, low T,


    allylic RX)

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