Scribd Logo
Upload

Welcome to Scribd!

  • 293 views

    Mesomeric Effect

    Uploaded by

    Awais Arshad
    The most acidic hydrogen is present in compound (c) as it has an α-hydrogen to a carbonyl group with no alkyl substitution. The order of acidity is: (c) > (a) > (d) > (b) Hence, the most acidic hydrogen is present in option (c).

    Copyright:

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

    Mesomeric Effect

    Uploaded by

    Awais Arshad
    293 views21 pages
    The most acidic hydrogen is present in compound (c) as it has an α-hydrogen to a carbonyl group with no alkyl substitution. The order of acidity is: (c) > (a) > (d) > (b) Hence, the most acidic hydrogen is present in option (c).

    Original Description:

    mesomeric effect

    Original Title

    mesomeric effect

    Copyright

    © © All Rights Reserved

    Available Formats

    PPTX, PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    The most acidic hydrogen is present in compound (c) as it has an α-hydrogen to a carbonyl group with no alkyl substitution. The order of acidity is: (c) > (a) > (d) > (b) Hence, the most acidic hydrogen is present in option (c).

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    293 views21 pages

    Mesomeric Effect

    Uploaded by

    Awais Arshad
    The most acidic hydrogen is present in compound (c) as it has an α-hydrogen to a carbonyl group with no alkyl substitution. The order of acidity is: (c) > (a) > (d) > (b) Hence, the most acidic hydrogen is present in option (c).

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    of 21

    Electromeric Effect

    Temporary effect which is observed


    in presence of reagents involving
    transfer of electrons in an unsaturated
    system.

    in presence
    of reagent + –
    X Y X Y
    in absence
    of reagent
    Electromeric Effect
    Addition of HBr to an alkene

    R 2 R
    1 H H
    HBr
    C C C—C
    H H + – H
    H
    R
    Br
    – + +
    H
    R — CH — CH3 C — CH3
    H
    Br
    Hyperconjugation or no bond resonance
    (a) Involves  and  bond orbitals
    (b) More the number of hyperconjugative
    structures, more will be the stability of
    ion or molecule

    + H H
    H H H H H
    +
    + H–C=C
    H–C–C H–C=C–H H C=C
    +
    H H H H H H H H

    Structure of ethyl carbonium ion


    Hyperconjugation or no bond resonance
    (c) The number of hyperconjugative structures in an alkene is
    obtained by the number of C — H bonds attached to the carbon
    bonded directly to the double bonded carbon atoms.

    H H+ H
    –
    H
    + C CH
    –
    CH2
    H C CH CH2 H C CH CH2

    H H H

    H
    –
    H C CH CH2

    H
    +
    Significance of Hyperconjugation
    H
    C
    —
    3
    CH
    —C
    HC
    H2
    H
    C
    —
    3C
    HC
    H
    — C
    H2
    +
    H
    1–butene (
    2h
    yp
    e
    r
    co
    nj
    uga
    t
    i
    ves
    t
    r
    uct
    ur
    es
    )

    –
    H
    C
    —
    3
    C
    HCH
    —C
    H3 H
    C
    — C
    H
    —CHC
    H2
    3
    +
    H
    (
    6hy
    p
    er
    co
    nj
    uga
    t
    i
    ves
    t
    ru
    ct
    ur
    es
    )
    2–butene

    More stable
    Relative strength of organic acids

    O O
    R-C O
    R-C + +
    H R-C
    OH O O

    Resonance structures
    Class exercise
    Allyl isocyanide has
    2
    (a) 9 bonds and 4 bonds
     
    (b) 8 bonds and 5 bonds
     
    (c) 8 bonds, 5 bonds and 4 non-bonding electrons
     2 non-bonding electrons
     2 bonds and
    (d) 9 bonds,

     

    Solution: + –
    H2C CH — CH2 — N C
    Allyl isocyanide
    The compound has 3 p bonds and one lone pair, i.e.
    two non-bonding electrons. It also contains 9 s-bonds.

    Hence answer is (d).


    Class exercise 3
    Among the following which has the most acidic
    -hydrogen? 
    O O O

    (a) CH3CCH2CHO (b) CH3CCH2CCH3

    (c) C
    H C C
    H C O
    OCH (d) CH3CHO
    3 2 3

    You might also like