Top Banner

of 29

18 CH203 Fall 2014 Lecture 18 October 15.pdf

Jun 02, 2018

Download

Documents

BUCH203
Welcome message from author
This document is posted to help you gain knowledge. Please leave a comment to let me know what you think about it! Share it to your friends and learn new things together.
Transcript
  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    1/29

    !

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    2/29

    #$%&' ()*+,-) !./*+01)- !23 %&!4

    567 7)89):

    %

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    3/29

    ;?0-@=A0> 9B *0>+=9>)C 9> => 567 BD)*+-,@E

    !F

    G 0? +=>*) 9> DD@

    K*@)>+ 0? ++ -)B0>=>*)BF G)HHB

    ,B I B)+B 0? >0>)O,98=H)>+ B =-)D-)B)>+F

    'F G,@1)- 0? B 9> )=*< >0>)O,98=H)>+ B)+

    1I 9>+)J-=A0>F

    4F G,@1)- 0? >)9JJ BF

    2F

    G+=A0> 0? +)9JJ B

    K*0,DH9>J *0>B+=>+MF

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    4/29

    # 9+B 9@@)C9=+)

    )>89-0>@)>+F

    QH)*+-0>)J=A8) =+0@B :9+

    C)>B9+I3 C)BJ +3 =>C BJ

    9+B B9J>=H +0

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    5/29

    # 9+B 9@@)C9=+) )>89-0>@)>+F

    S09>C,*)B )H)*+-0>T-9*< D9T10>C)C ?,>*A0>=H J-0,DB +0

    D-0C,*) B)*0>C=-I @=J>)A* R)HCB :C9>J 0> ++=A0> +0 +)A* =>9B0+-0D9* R)HCF

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    6/29

    #B =-) +0 + >,*H),BF

    G

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    7/29

    XD9>TBD9> *0,DH9>J

    Y

    K!Z !M-,H)[\? = 0>)O,98=H)>++0 9+ 1,+ )O,98=H)>+ =@0>J

    + ++ =+0@KBM3 9+B !$T567

    B9J>=H 9B BDH9+ 9>+0 K!Z !M

    D)=^BF

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    8/29

    XD9>TBD9> *0,DH9>J

    \? $=BDH9+B $1:9+< = *0,DH9>J *0>B+=>+"3 + $1BDH9+B $=:9+< +J *0>B+=>+F

    \? I0, B)) +

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    9/29

    XD9>TBD9> *0,DH9>J :" 8=H,)B =-) B9@9H=-

    "=1=>C"1* =-) *H0B) +0 +9+,C)

    1)*=,B) + = P)_91H) *F 70+=A0>

    =8)-=J)B +J *0>B+=>+B +0 =10,+ + J)>)-=H3 : Z!M _ K@ Z!M D)=^B3 = P)_91H) BIB+)@ H9^) + Z @ Z!M D)=^BF

    K> Z!M _ K@ Z!M ` a D)=^B )_D)*+)C

    K> Z @ Z!M ` 2 D)=^B 01B)-8)C

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    10/29

    XD9>TBD9> *0,DH9>J

    C C

    HH

    C C

    H H

    C C

    H

    H

    C C

    H

    H

    H

    H

    C C

    H

    C H

    H

    H

    H

    H

    H

    H

    $"3 89*9>=H

    UT. $V

    $"3 89>IH9* %&'

    2T!& $V

    $"3 89>IH9* ()*!'

    !!T!. $V

    +"3 89>IH9* ,-.&!*/

    &T2 $V

    +"3 ,-.&!*/

    &T2 $V

    0"3 =HHIH9*

    &T! $V

    +"3 1)(21

    YTa $V

    $"3 @)+=

    %T' $V

    0"33*)*

    &T! $V

    G9+,C) 0? +J *0>B+=>+

    +)HHB ,B B0@)+J

    =10,+ +C

    J)0@)+-9*

    -)H=A0>B

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    11/29

    GJ *0>B+=>+3 b3 =>C + D-0+0>B :9+C &d C9JH)B =>C +J :9HH 1) H)=B+ ?0- D-0+0>B +

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    12/29

    5,@1)- 0? B 1I 9>+)J-=A0> 0? +=H

    (-)(TS,+IH =*)+=+) KB@)HHB H9^) 1H,)1)--9)BM + B =>C =@0H)*,H=- ?0-@,H= 0? #U$!%/%F G,@1)- 0? B 9B !%F G+)J-=H

    9> +

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    13/29

    ; B C9B=DD)=-

    G*) 0? +

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    14/29

    ; B C9B=DD)=-

    fCC9>J => )_*)BB 0? g%/ +0 ++ )_*J)B =HH + + +

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    15/29

    ; B C9B=DD)=-

    $IC-0J)> =+0@B 10>C)C +0 0_IJ)> 0- >9+-0J)> =+0@B *=> )_*J) :9+< )=*< 0+*A0>=H J-0,DB =N)*+)C 9>*H,C)

    *=-10_IH9* =*9CB3 =H*0)B3 =>C =@9C)BF X9J>=HB ?0- )_*J9>J $ =+0@B =-) J)>)-=HHI

    1-0=C B9>JH)+B +0+ +=^) D=-+ 9> BDH9h>J :9+< 0+=HBF

    A. Pentanoic acid (valeric acid)

    Figure 16100 MHz 1H-NMR spectrum of pentanoic acid.

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    16/29

    ; B C9B=DD)=-B.

    Trans-2-hexenoic acid

    Figure 17 100 MHz 1H-NMR trans-2-hexenoic acid.

    Figure 18100 MHz 1H-NMR spectrum of cyclobutanecarboxylic acid.

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    17/29

    !$ 567 D-01H)@

    #0@D0,>C :9+< = @0H)*,H=- ?0-@,H= 0? #4$a#H

    !$ 567[

    'F'. DD@ KC3 b`U $V3 %$M

    !Fa2 DD@ K@3 !$M

    !F&! DD@ KC3 b`UFU $V3 U$M

    !'# 567[

    2%F4a DD@

    '!F&U DD@

    %&F&. DD@

    !Y

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    18/29

    !$ 567 D-01H)@

    #0@D0,>C :9+< = @0H)*,H=- ?0-@,H= 0? #4$a#H

    !$ 567[

    'F'. DD@ KC3 b`U $V3 %$M

    !Fa2 DD@ K@3 !$M

    !F&! DD@ KC3 b`UFU $V3 U$M

    !'# 567[

    2%F4a DD@

    '!F&U DD@

    %&F&. DD@

    G \$g 0? &3 +)HHB @) +0 -9>JB 0- C0,1H) 10>CBF

    G

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    19/29

    !$ 567 D-01H)@

    #0@D0,>C :9+< = @0H)*,H=- ?0-@,H= 0? #4$a#H

    !$ 567[

    'F'. DD@ KC3 b`U $V3 %$M

    !Fa2 DD@ K@3 !$M

    !F&! DD@ KC3 b`UFU $V3 U$M

    !'# 567[

    2%F4a DD@

    '!F&U DD@

    %&F&. DD@

    G

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    20/29

    !$ 567 D-01H)@

    #0@D0,>C :9+< = @0H)*,H=- ?0-@,H= 0? #4$a#H

    !$ 567[

    'F'. DD@ KC3 b`U $V3 %$M

    !Fa2 DD@ K@3 !$M

    !F&! DD@ KC3 b`UFU $V3 U$M

    !'# 567[

    2%F4a DD@

    '!F&U DD@

    %&F&. DD@

    G 9B0D-0DIH J-0,D D-)B)>+ 1=B)C 0> +C@,HADH)+ B9J>=HBF G +

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    21/29

    !$ 567 D-01H)@

    #0@D0,>C :9+< = @0H)*,H=- ?0-@,H= 0? #4$a#H

    !$ 567[

    'F'. DD@ KC3 b`U $V3 %$M

    !Fa2 DD@ K@3 !$M

    !F&! DD@ KC3 b`UFU $V3 U$M

    !'# 567[

    2%F4a DD@

    '!F&U DD@

    %&F&. DD@

    G

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    22/29

    !$ 567 D-01H)@

    #0@D0,>C :9+< = @0H)*,H=- ?0-@,H= 0? #4$a#H

    !$ 567[

    'F'. DD@ KC3 b`U $V3 %$M

    !Fa2 DD@ K@3 !$M

    !F&! DD@ KC3 b`UFU $V3 U$M

    !'# 567[

    2%F4a DD@

    '!F&U DD@

    %&F&. DD@

    R CH3

    CH3H

    Cl R +

    Cl

    CH3

    CH3

    #0@19>) ?-=J@)>+B =>C *=H B+-,*+,-)B =J=9>B+ 567 C=+=F

    %%

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    23/29

    !$ 567 D-01H)@

    #U$!4/%lH+-=D,-) B=@DH)

    %'

    %$

    !%$

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    24/29

    !$ 567 D-01H)@

    #U$!4/%lH+-=D,-) B=@DH)

    %4

    %$

    !%$

    CH3

    OH

    CH3

    HO

    H3C

    H3C

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    25/29

    !$ 567 D-01H)@

    #2$Y5/%

    %2

    %$

    '$%$

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    26/29

    !$ 567 D-01H)@

    #2$Y5/%

    %U

    %$

    '$%$

    C O

    O

    N

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    27/29

    !$ 567 D-01H)@

    #4$Y#H

    %Y

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    28/29

    !$ 567 D-01H)@

    #4$Y#H

    %.

    Cl

  • 8/10/2019 18 CH203 Fall 2014 Lecture 18 October 15.pdf

    29/29

    %a