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    Haloalkanes, Alcohols and Amines. Problem Sheet 1

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    Kundan Kumar Singh
    The document provides 7 reaction problems involving haloalkanes, alcohols and amines. It examines the reactivity of various alkyl halides in SN1 and SN2 reactions, and asks students to predict products, mechanisms, and stereochemical outcomes. It also asks students to explain reaction rates and the stereochemical consequences of SN2 reactions at chiral centers.

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    Haloalkanes, Alcohols and Amines. Problem Sheet 1

    Uploaded by

    Kundan Kumar Singh
    49 views2 pages
    The document provides 7 reaction problems involving haloalkanes, alcohols and amines. It examines the reactivity of various alkyl halides in SN1 and SN2 reactions, and asks students to predict products, mechanisms, and stereochemical outcomes. It also asks students to explain reaction rates and the stereochemical consequences of SN2 reactions at chiral centers.

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    DCB-Problemsheet1

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    The document provides 7 reaction problems involving haloalkanes, alcohols and amines. It examines the reactivity of various alkyl halides in SN1 and SN2 reactions, and asks students to predict products, mechanisms, and stereochemical outcomes. It also asks students to explain reaction rates and the stereochemical consequences of SN2 reactions at chiral centers.

    Copyright:

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

    Haloalkanes, Alcohols and Amines. Problem Sheet 1

    Uploaded by

    Kundan Kumar Singh
    The document provides 7 reaction problems involving haloalkanes, alcohols and amines. It examines the reactivity of various alkyl halides in SN1 and SN2 reactions, and asks students to predict products, mechanisms, and stereochemical outcomes. It also asks students to explain reaction rates and the stereochemical consequences of SN2 reactions at chiral centers.

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    © All Rights Reserved
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    Haloalkanes, Alcohols and Amines.

    Problem Sheet 1
    1. Arrange these compounds in order of increasing reactivity for SN2 displacement:

    (a) 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, 3-bromo-2-methylbutane


    (b) 1-bromopentane, 1-bromo-2,2-dimethylpropane, 1-bromo-3-methylbutane.

    2. In the following nucleophilic substitution reactions, predict the product and provide
    the mechanism. In each case state whether the mechanism proceeds by SN1 or SN2.

    Bu3P + EtI

    PhMe2CCl + EtOH

    Br
    N + NaI

    3. When optically active 2-iodooctane was allowed to stand in acetone solution


    containing Na128 I (radioactive iodine), the alkyl halide was observed to lose optical
    activity and to exchange its ordinary iodine for radioactive iodine. The rate of these
    reactions depended on both [RI] and [128 I-], but the loss of optical activity was exactly
    twice as fast as gain of radioactivity. This unambiguously establishes that in the SN2
    mechanism, each molecule undergoing substitution suffers inversion of configuration.
    Explain.

    4. Provide a mechanism for the following transformation. What is the by-product from
    the reaction? Classify the key carbon-oxygen breaking step as SN1 or SN2.

    OMe OH
    HI

    5. Provide mechanisms for the following transformations.

    H2SO4
    OH
    O

    AgNO3, H2O

    Cl OH
    6. When either but-2-en-1-ol OR but-3-en-2-ol is allowed to react with HBr, the same
    product distibution of 1:4 of A:B is produced. Explain.

    Br
    Br
    A B

    7. Explain the observed reaction rates when the bromides below where solvolysed in
    EtOH.

    Br Br Br

    rel. rate: 1 10-6 10-14

    8. What is the usual stereochemical consequence of the S N2 mechanism if the attacked


    carbon centre is chiral? Rationalise the following.

    Et Et
    Et KOH Et
    HO Cl HO OH
    Me Me
    H H

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