Shapes of Simple Organic Molecules

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    SHAPES OF SIMPLEORGANIC MOLECULES

    HYBRIDIZATION AND RESONANCE

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    Types of Atomic Orbitalpreset i carbo t!at

    cotai electros1s orbital- spherical

    2s orbital- spherical

    2p orbitals- lobes

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    P orbital

     There are three porbitals- 2px 2p! a"#

    2p$

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    P orbital

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    Bonding

    Energy

    1s

    2s

    2px

      2py

      2pz

    Ground State of Carbon

     The %ro&"# state co"'%&ratio" o(carbo" is &"s&itable (or bo"#i"%)

     I" the %ro&"# state carbo" ca"o"l! (or* three bo"#s +&"e,&alle"%th a"# stre"%th)  .or /correct0 bo"#i"% to occ&rso*e cha"%es hae to be *a#e i"the orbitals)

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    Orbital Changes- Excitation

    Energy

    1s

    2s

    2px   2py   2pz

    Ground State of Carbon

    Energy

    1s

    2s

    2px   2py   2pz

    Excited State of Carbon

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    Orbital Changes- Hybridizationsp3

    Energy

    1s

    2s

    2px   2py   2pz

    Excited State of Carbon

    Energy

    1s

    sp3 Hybridized State of Carbon

    sp3

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    sp3 hybridized orbital

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    sp3 hybridized orbital

    S a"# p orbitalsSp orbitals

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    "o#i$ 

    i 

    Met!ae 

    %CH&'0

     Oerlap o(  s a"# sp orbitals (or* si%*a +3 bo"#

    0 Carbo" ato* is sp3 hybridized 

    0 

    Bo"#s are (or*e# b! 

    oerlappi"% 

    o(  

    the 

    1s 

    orbitals o(  (o&r h!#ro%e" ato*s 4ith the sp3 orbitals o(  the carbo" ato*

    Met!ae !as & ( 

    bo#s

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     N ote that each bond contains 2

    electrons: 1 from s orbital of hydrogen

    1 from sp3 orbital of carbon

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    "o#i$ 

    i 

    Et!ee 

    %C)H&'

    0 Ethe"e co"tai"s a #o&ble bo"#

    0 

    I" 

    carbo" 

    o(  

    #o&ble 

    bo"# 

    there 

    are 

    three sp2 h!bri# orbitals a"# one &"&se# p orbital

    0 Each carbo" i" the #o&ble bo"# is sp2 

    hybridised 0

     5"&se# p orbital oerlaps aboe a"# belo4 the 

    pla"e 

    to 

    (or* 

    a 

    pi 

    +6 

    bo"#

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    !ttp*++,,,-citycolle$iate-com+!ybri#i.atio)-!tm

    http://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htmhttp://www.citycollegiate.com/hybridization2.htm

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    "o#i$ 

    i 

    Et!ye 

    %C)H)'

    0 

    Eth!"e co"tai"s a triple bo"#0

     

    I" carbo" o(  triple bo"# there are two sp h!bri# 

    orbitals 

    a"# 

    two 

    &"&se# 

    p 

    orbital0

     Each carbo" i" the triple bo"# is sp hybridised 0

      The t4o &"&se# p orbitals oerlap aboe a"# belo4 the pla"e to (or* t4o pi +6 bo"#s

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    ✓  The 

    triple 

    bo"# 

    co"sists 

    o(  

    o"e 

    si%*a bo"#

     

    a"# 

    t4o 

    pi 

    bo"#s✓  The %eo*etr! aro&"# each carbo" is 

    li"ear 4ith a bo"# a"%le o(  178o

    http9::pa%es)to4so")e#&:la#o":carbo")ht*l

    http://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.htmlhttp://pages.towson.edu/ladon/carbon.html

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    "e.eeSix carbo" ato*s i" a ri"%

    Sho4s reso"a"ce h!bri#isatio"

    Hexa%o"al i" shape - at each apex there is acarbo" bo"#e# to a h!#ro%e"

    Each carbo" is bo"#e# to three other ato*s; a

    h!#ro%e" a"# t4o other carbo" ato*s

    Each carbo" &ses sp2 h!bri# orbitals

    Each carbo" co"tai"s a p&re p orbital

    perpe"#ic&lar to the pla"e o( the ri"%

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    "e.ee

    Each &"h!bri#i$e# p orbitaloerlaps 4ith t4o other porbitals o"e o" each o( the t4o

    "ei%hbo&ri"% carbo" ato*s

    A lar%e circ&lar pi-t!pe bo"# is(or*e# aboe a"# belo4 thepla"e

    Electro"s are #elocali$e# i" the

    be"$e"e ri"%

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    "e.ee

    Oerlappi"% o( p orbitals

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    "e.ee

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    "e.ee

    Ca"o"ical (or*s

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    "e.ee

    H!bri#i$e# str&ct&re


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