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    Substitution Vs Elimination Practice Problems 3 Answer Key Rev42213 PDF

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    samfarmer333
    This document provides 12 practice problems for predicting organic reaction mechanisms and products. For each reaction, students are asked to name the mechanism by which the major product is formed and explain their reasoning. The examples cover substitution and elimination reactions involving alcohols, alkyl halides, and other functional groups under various conditions to illustrate different reaction pathways such as SN1, SN2, E1 and E2.

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    Substitution Vs Elimination Practice Problems 3 Answer Key Rev42213 PDF

    Uploaded by

    samfarmer333
    213 views3 pages
    This document provides 12 practice problems for predicting organic reaction mechanisms and products. For each reaction, students are asked to name the mechanism by which the major product is formed and explain their reasoning. The examples cover substitution and elimination reactions involving alcohols, alkyl halides, and other functional groups under various conditions to illustrate different reaction pathways such as SN1, SN2, E1 and E2.

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    169315729-Substitution-vs-elimination-practice-problems-3-answer-key-rev42213-pdf.pdf

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    This document provides 12 practice problems for predicting organic reaction mechanisms and products. For each reaction, students are asked to name the mechanism by which the major product is formed and explain their reasoning. The examples cover substitution and elimination reactions involving alcohols, alkyl halides, and other functional groups under various conditions to illustrate different reaction pathways such as SN1, SN2, E1 and E2.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    213 views3 pages

    Substitution Vs Elimination Practice Problems 3 Answer Key Rev42213 PDF

    Uploaded by

    samfarmer333
    This document provides 12 practice problems for predicting organic reaction mechanisms and products. For each reaction, students are asked to name the mechanism by which the major product is formed and explain their reasoning. The examples cover substitution and elimination reactions involving alcohols, alkyl halides, and other functional groups under various conditions to illustrate different reaction pathways such as SN1, SN2, E1 and E2.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 3
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    The text discusses various organic reactions and identifies the reaction mechanisms (SN1, SN2, E1, E2) based on factors such as the structure of the reactants, the conditions used, and the ability of the reactants to form carbocations or act as nucleophiles/leaving groups.

    The text notes that reaction conditions like the type of solvent, temperature, acid/base strength and nucleophilicity/leaving group ability influence whether a reaction proceeds by a substitution or elimination pathway.

    The text identifies several factors that determine the reaction mechanism including the structure of the substrate (steric hindrance), ability to form stable carbocations, strength/nucleophilicity of the base, and ability of the substrate to act as a leaving group.

    Practice problems 3: Substitution or elimination?

    CHM 235
    Answer key Minger
    Predict the major organic product of each of the following reactions. Write the name of the
    mechanism by which the product is formed and make notes about how you arrived at your
    conclusion. The first three are done for you to suggest a general method of how to analyze
    these problems.

    CH3 CH3ONa E2. Sterically hindered


    1. substrate; strong base,
    Cl CH3OH good leaving group.
    CH3

    CH2CH3 CH2CH3
    CH2CH3
    2. +
    OCH3 CH3
    Cl CH3OH CH3 OCH3
    CH3

    SN1/E1. Sterically hindered


    substrate can form a stable
    +
    carbocation. Weak base/
    poor nucleophile. Notice the
    mixture of inversion and
    retention of configuration in
    the substitution products.
    Some E1 product may also
    form.

    CH3 CH3
    Br CN
    NaCN
    3.
    DMSO

    SN2. Excellent nucleophile, excellent leaving group.


    Polar aprotic solvent is a clue to SN2 pathway. (Cyanide
    can also effect E2 reaction.)

    OCH3 H2SO4 E1. Dehydration conditions work


    4.
    the same on OR as they do on OH.
    The O in the OCH3 group is protonated
    and the reaction proceeds in an
    identical manner as what we have seen
    with alcohols. Note that the double/single/
    double bond pattern formed, called
    conjugation, is particularly stable.

    4/22/13
    CH3 KBr CH3
    SN2. Secondary substrate, good nucleophile,
    5.
    I DMSO H polar aprotic solvent. Inversion of configuration.
    H Br

    E2. Substrate is quite hindered.


    LDA is a strong, sterically hindered base
    CH3 LDA CH3 (and a poor nucleophile because of its
    6. steric hindrance) that is used for
    I CH3 DMF CH3
    elimination reactions. Conjugation of the
    new double bond with the benzene
    ring (see #4) is also favorable.

    H3C Br
    H3C HBr
    7. +
    Br H3C
    EtO 0 oC
    CH3 CH3
    CH3
    SN1. The EtO group gets protonated by HBr and leaves as ethanol,
    (Et = CH2CH3) forming a carbocation which is then captured by bromide, a good
    nucleophile. Low temp discourages elimination pathway. Planar
    carbocation is attacked from above or below by bromide, resulting in
    product mixture.

    KN3 CH3 SN2. Secondary substrate; azide is a


    8. CH3
    good nucleophile; polar aprotic solvent.
    I H DMF H N3
    Inversion of configuration.

    E2. Steric hindrance prevents


    methoxide from nucleophilic attack.
    H3C Br CH3ONa Bromide is an excellent leaving group
    9.
    and conjugation of the new double bond
    DMSO
    with the ring (see #4) is an additional
    driving force. Steric hindrance is a more
    important factor than the polar aprotic
    solvent. If the nucleophile can't approach,
    no solvent can help that!

    H3C H3C AcO


    10.
    Cl OAc + CH3
    O

    OH O
    OAc =
    O

    SN1. Polar protic solvent (acetic acid) that's a weak nucleophile and tertiary substrate encourage
    unimolecular substitution. Notice mixture of retention and inversion of configuration in product.
    E1 elimination is possible as well.

    4/22/13
    CH3 H3PO4 E1. Dehydrating conditions give the alkene
    11.
    after carbocation rearrangement.
    OH

    Br KOH(aq)
    12.
    OH (dilute)

    SN2. The first step is a deprotonation. In the presence of hydroxide ion, the alcohol will be
    deprotonated (compare pKa values of water and alcohols to estimate the extent of this
    deprotonation):

    Br Br
    KOH
    OH O O

    There could also be some direct displacement of bromide ion by hydroxide, although the
    proton transfer shown above is faster:

    HO
    Br OH

    OH OH

    4/22/13

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