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    Compound A Reacts Faster by The S 1 Mechanism Than Compound B

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    Shravani Khot

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    Compound A Reacts Faster by The S 1 Mechanism Than Compound B

    Uploaded by

    Shravani Khot
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    © All Rights Reserved
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    5 views47 pages

    Compound A Reacts Faster by The S 1 Mechanism Than Compound B

    Uploaded by

    Shravani Khot

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    Q.

    Compound A reacts faster by the SN2 mechanism than the compound B

    Q. Compound A reacts faster by the SN1 mechanism than compound B


    Reactive differences between axial and equatorial conformers

    Nu-

    TS

    Nu-

    Nu- = -SPh
    X- = -OTs TS
    Reaction 1 found to be 31 times faster than 2

    hindered by axial
    hydrogens
    Which of the following compound will be faster reacting
    under the given reaction condition?
    Epoxide formation

    No epoxide

    Only diaxial conformation forms epoxide


    E2 eliminations have anti-periplanar transition states

    Two conformations with H and X coplanar

    In E2 eliminations, the new π bond is formed by overlap of the


    C-H σ bond with the C-X σ* antibonding orbital
    E2 Stereochemistry

    E2 reactions occur most rapidly when the H-C bond and C-LG bonds involved are
    co-planar, most often at 180o with respect to each other. This is described as
    an antiperiplanar conformation. This conformation positions the σ bonds that are
    being broken in the correct alignment to become the π bond.

    The staggered, antiperiplanar alignment is preferred


    because it aligns the two σ bonds that become the π bond.
    Synperiplanar arrangments where the angle between the H-C bond
    and C-LG is 0o are also known, usually in systems that are either inflexible
    rings or intramolecular eliminations.

    The eclipsed, synperiplanar alignment also aligns the two


    σ bonds that become the π bond, but is less favourable than
    the antiperiplanar arrangement.

    These alignments are example of a stereoelectronic effect because they involve the
    specific spatial positioning of the bonds (electrons) in order for the process to occur

    We will discuss “Syn” elimination at a later stage


    E2 eliminations have anti-periplanar transition states

    Me groups gauche Me groups


    (syn-clinal) anti-periplanar
    more hindered Less hindered

    Reaction is stereoselective
    Only one proton for removal
    Whereas
    Relative reactivity of alkyl halides in E2 elimination
    Relative reactivity of alkyl halides in E2 reaction
    Tertiary alkyl halides > secondary alkyl halides > primary alkyl halides

    Stability of the generated alkene is the decisive factor

    Q1. Which alkyl halide in each pair is more reactive in an E2 reaction with NaOH
    Q2. Which alkyl halide in each pair is more reactive in an E2 reaction with NaOH
    Q.

    Slow
    Anti 1,2-elimination and conformational requirements
    Q1. Among the two given compounds (A & B) one undergoes E2 reaction
    swiftly with NaOMe/MeOH than the other. Identify A and B with proper
    reason

    Q2. Explain the following reaction with proper explanation


    Q.

    S N2
    Reactions of 2-bromo-4-phenylcyclohexanols with base and silver oxide

    Ag2O
    or OH- Ag2O Ag2O
    or OH- Or OH-

    Stable not suitable for -HBr

    Ag2O
    Ag2O induces –Br -

    OH-
    Esterification and hydrolysis reaction of conformationally locked cyclohexane systems
    Esterification and hydrolysis reaction of conformationally locked cyclohexane systems
    Which of the following isomer will be tosylated first with 1 eq
    of Ts-Cl and pyridine? Explain your answer with proper reasoning.
    Also predict the proper stereochemistry of the final product?
    Arrange the following alcohols in order of decreasing rate
    of esterification with para-nitrobenzoyl chloride?
    Esterification and hydrolysis reaction of conformationally locked cyclohexane systems
    Which compound should saponify faster (A or B)?
    Explain the relative rate differences?
    Which of the “OH” group in the following compound will oxidize
    rapidly in presence of PCC. Explain your answer with proper reasoning?

    The secondary axial alcohol will be oxidized first.

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