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    All of the following reactions involve at least one pericyclic process (a number of the problems involve multiple péricyclic processes) in each case: i) provide a mechanism for the reactions ii) identify the pericyclnic process or processes iii) assign them to their class iv) show they are allowed using either the woodward--hoffmann rules or an FMO analysis v) Predict the stereochemical outcome of the reaction where it is not shown (wavy bond) or rationalis

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    All of the following reactions involve at least one pericyclic process (a number of the problems involve multiple péricyclic processes) in each case: i) provide a mechanism for the reactions ii) identify the pericyclnic process or processes iii) assign them to their class iv) show they are allowed using either the woodward--hoffmann rules or an FMO analysis v) Predict the stereochemical outcome of the reaction where it is not shown (wavy bond) or rationalis

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    114 views5 pages

    Problems O and M3

    Uploaded by

    anon_190724360
    All of the following reactions involve at least one pericyclic process (a number of the problems involve multiple péricyclic processes) in each case: i) provide a mechanism for the reactions ii) identify the pericyclnic process or processes iii) assign them to their class iv) show they are allowed using either the woodward--hoffmann rules or an FMO analysis v) Predict the stereochemical outcome of the reaction where it is not shown (wavy bond) or rationalis

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    of 5

    Orbitals

    and Mechanism III

    Jonathan W. Burton

    Practice Problems Relating to Pericyclic Reactions



    All of the following reactions involve at least one pericyclic process (a number of the
    problems involve multiple pericyclic processes).
    In each case:
    i)
    provide a mechanism for the reactions
    ii)
    identify the pericyclic process or processes
    iii)
    assign them to their class
    iv)
    show they are allowed using either the Woodward-Hoffmann rules or an FMO
    analysis
    v)
    Predict the stereochemical outcome of the reaction where it is not shown (wavy
    bond) or rationalise the stereochemical outcome where it is shown.

    1)
    '!($%



    2)

    !"#$%&

    #.
    ##.*$%!/
    ###.*'/(0(
    #1.*/&!2

    !
    )*+%,-

    '!($%
    '!($%
    !

    '!($%

    !"#$


    3)
    $%

    &#'(

    "#

    "#

    $%


    4)
    !"#$


    5)
    !

    '

    +
    "#$%&

    (#)*
    &$%"#

    "#$%&

    '
    &$%"#

    "#$%&

    &$%"#

    Orbitals and Mechanism III

    Jonathan W. Burton

    6)

    "#$%

    !&


    7)
    &

    &

    !"#$%&#"

    &

    &


    8)

    "
    heat in DMSO

    #$
    !


    9)
    "!$

    " !

    ()"#!*+%&,"

    '
    #!$%&

    #!$%&


    10)
    !

    "#$

    %"&'(

    )(*+

    +
    %"&'(

    "#$
    %"&'(


    11)
    "#$%


    12)
    !


    #$
    %
    !

    #$%"!"

    "


    13)
    !

    "#$

    '("&%

    #$"

    "#$%

    Orbitals and Mechanism III

    Jonathan W. Burton

    14)
    "#

    "#

    "#

    $%&'

    but

    $%&'

    ()*+%&,-)(


    15)
    %&'(

    $
    $
    $"#!

    !"#$


    16)

    &'()*+&,(-.#/(0"123
    &&'("#)4
    &&&'(256,("#2!,(4#7*8

    !"#$

    %
    !

    !
    %

    "#


    17)
    &'
    !

    heat

    %
    $

    &'

    ! &'

    (
    $

    "#

    "# $

    "#


    18)
    #(

    "#

    ($

    %(;%(&'

    23456"-"4/4789":-/4<23456"-/6="4"-3289":


    19)

    %#$&'
    !"#$%

    23456"-"4/4789":

    %&'(
    "#

    %()%*#&'+),-./'0-&'%#$(,-1"/'
    &'

    !"#$%

    "#

    "#

    ($
    (!&'

    )#*%
    $

    "#
    !

    ($

    Orbitals and Mechanism III

    Jonathan W. Burton

    20)
    !"

    !"

    $
    $!%&

    %'()$*+,

    !"

    #
    !"

    $#

    !"

    #
    !"

    # $



    Practice Problems Relating to Radical Reactions
    Provide mechanisms for the following reactions. In each case explain the selectivity of the
    reaction in as much detail as possible.

    1)
    #

    !" #

    $%&'()*

    !"

    ")'%

    +)

    !"


    2)
    !

    "!#

    $%&'(

    !
    #

    !
    $)*'(

    !
    *'+,'-./(0/1


    3)
    !"
    #

    !"

    &!

    %
    #$

    #$


    4)
    !
    !

    #$!

    "
    %&'()*+,,*+-)+!

    #$!

    !
    !
    !

    "


    5)
    !

    %&'()*+,-.%"+,$/01

    ()%&'
    2,,"3

    "

    "

    #$

    #$

    Orbitals and Mechanism III

    Jonathan W. Burton

    6)
    #

    BuSH, AIBN, heat

    !"

    !"

    %&'
    $


    7)

    %&
    !

    !
    #$

    #$

    Bu3SnH, AIBN, heat

    !"


    8)

    +
    !"

    %
    !"#$

    &'(#)*+,-.&/+,"$01


    9)
    1

    ,-./
    0$

    !"#$%&'()*!+'(,-./

    +
    $


    10)
    #

    $%
    #

    $%
    !"

    BrCCl3
    &

    '

    h!
    #

    0&

    !"

    ()
    #

    '



    Bibliography for Radical Reactions

    Reactive Intermediates, Oxford Chemistry Primer no. 8; Christopher Moody and Gordon
    Whitham
    Organic Chemistry Jonathan Clayden, Nick Greeves, Stuart Warren, Peter Wothers
    Frontier Orbitals and Organic Chemical Reactions; Ian Fleming
    Molecular Orbitals & Organic Chemical Reactions; Ian Fleming
    Rearrangements and Reactive Intermediates Lecture notes and problems; Harry
    Anderson


    Problems and complete filled in handout available at:
    http://burton.chem.ox.ac.uk/teaching.htm
    5

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