ベンゼン環を含む - coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfoh ona naoh...

18
49 2012 Ûݨ͜ 25 ¿ (óáƮƓÖ ƪâ) n|W|IJA¸6ĊĔ¨´Į FE t-f`, Ō!+),ƬÔ(ųŐ8"$8 2 ŏƦ+ŬĿžÌÁ$<Ƭ Ɓ+đìčĀ&$Ƭ4Ƭij¨Í°è+ŶÊ&$Ƭij»İż)ġƚ @"$=ƭŌ!+)ÌÁ=ŬĿž+ÂČƩĐ,Ƭ1$ 20 ŏƦ+ DtdƐ):"$ŗ5ő$;>$=ƭ>; 20 ŏƦ+DtdƐ+!Ƭ3 ŏƦ),n|W|IJ¸4>$=ƭ n|W|IJ,4ƬªŪ½+ÂČƩĐ&$8ĵ;>$=ƭ)ŋ 3 ŏƦ+¨´Į,Ƭ>8Ɨļ¤&$ĵ;>$=8+%=ƭ ;)n|W|IJ,ƬƁ+¹<+rxs~+)8¸4>$=ƭo[_ q_y+ŕč%=rxHZz|]zkYz~_(PET)9ƬQ|ibH|UU _D%ŽÆ>$=Þá+ƆąkY)ĵ;>$=rxUZz|(PS)) O O OH O CH 3 H 3 C CH 3 CH 3 O OH CH 3 O OH O C C O O O O CH 2 CH 2 n CH 2 CH n NH 2 OH O NH 2 OH O HO N H OH O NH 2

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Page 1: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

49

2012ÛÝ�¨Íœ 25¿ (óáƮƓÖ ƪâ)

n|W|IJA¸6ĊĔ¨´Į

FEC ��t�-f�`��,C

Ō�!+��),ƬÔ(�ųŐ8"$8 2�ŏƦ+ŬĿž�ÌÁ�$�<ƬƁ�+đìčĀ&�$Ƭ4�Ƭij¨Í°è+ŶÊ&�$Ƭij»İż)ġ�ƚ

@"$�=ƭŌ�!+��)ÌÁ�=ŬĿž+ÂČƩĐ,Ƭ�1$ 20ŏƦ+DtdƐ):"$ŗ5ő$;>$�=ƭ�>; 20 ŏƦ+DtdƐ+�!Ƭ3ŏƦ),n|W|IJ�¸4>$�=ƭ

n|W|IJ,4�ƬªŪ½+ÂČƩĐ&�$8ĵ�;>$�=ƭ��)ŋ

� 3ŏƦ+¨´Į,Ƭ��>8Ɨļ¤&�$ĵ�;>$�=8+%=ƭ

�;)n|W|IJ,ƬƁ+¹<+rxs~+�)8¸4>$�=ƭo[_

q_y+ŕč%=rxHZz|]zkYz~_(PET)9ƬQ|ibH|UU_D%ŽÆ�>$�=Þá+ƆąkY)ĵ�;>$�=rxUZz|(PS))

O

O OH

O

CH3

H3C

CH3

CH3

O

OH

CH3

O

OHO

����� �� �� ����

C CO O

O O

CH2 CH2n CH2 CH n

������� �������� ���������

NH2

OH

O

NH2

OH

O

HO NH

OH

O

NH2

������� � �� ������

Page 2: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

50

,Ƭn|W|IJ�¸4>$�=ƭ�+:�)n|W|IJ,ƬĒ�(ĊĔ¨´

Į)¸4>$�=ƒŲg~\+�#%=ƭ�¿,�+n|W|IJ+��5

&êž)#�$ıŵAġ7:�ƭ

GEC ��t�]�B';C

n|W|, C6H6%;@�>=Ī¨ěŕ%=ƭ�+�Ë, 6 �+Īŕ­Ë�;ì=�äDyJ|�x|N)("�đƈA8"$�=ƭ�+�7Ƭ

n|W|A;@�đƈß&�$,Ƭ��+(a)%8(�(b)%8(�Ƭ(c)+:�(8+�/�@��&8Ş ;>=ƭÑƝƬ6 �+ C�C ř´+ƀƟ,��>8Ŕ���&�@�"$�=ƭ

(c)+đƈ,Ƭ(a)&(b)+ƒ*´@�&ıŵ�=�&�%�=ƭ#4<Ƭn

|W|�Ë,Ƭ(a)&�$+êž&(b)&�$+êžA�>�>Ŕ��ŋ��Ë%=Ƭ&��Ş ĂA�=�&�%�=ƭŷ�û =&Ƭ(a)8(b)8�>�>n|W|+êžAƍ�ŀ);@�đƈ%=&Ş ;>=ƭ

�+:�)Ƭn|W|A;@�đƈ(a)&(b),�B';&º->=*1ƭ�

ş+ƚ�,Ƭ(a)&(b)&Ař0�ƥҬ %;@�>=ƭ

�ƫđƈ,Ƭ­Ë+zEDF_,�+44)Ƭ­Ë&­ËAř0ř´Aŗ

5Ĉ �8+)("$�=ƭř´+ŗ5Ĉ AҬ):"$;@�&Ƭĕ

+:�)(=ƭ 1 �ƫđƈ)#�$,�ƐŕA¸6ĊĔ¨´Į+�Jyqby¨´Į%8ï"�ƭlx|_ 39o~T®Ĭƭ

C

CC

C

CC

C

CC

C

CC

(a) (b)

H

H

H

H H

H

H

H

H

H H

H

C

CC

C

CC

(c)

H

H

H

H H

H

C

CC

C

CC

C

CC

C

CC

H

H

H

H H

H

H

H

H

H H

H

Page 3: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

51

n|W|IJ,Ƭĕ+:�)Ņķ�$;@��&�È�ƭ

(a),Īŕ 6 ��;ì=x|N)�ơË�Ŕ���Ċ�>$�=�&Aŋ

�;@�Ă%=ƭ(b)�:.(c), 2ŏƦ+�ƫđƈ%=ƭƇÙƬ�>;3ŏƦA©¢�=�&(�ĵ�$�Ë+đƈA;@��&�È�ƭ�& -n|W|+ěŕ H� 1�Ƭh`{KS –OH)ŝû�>�¨´Į(kGd~y),Ƭĕ+'+ĂĞ%;@�$8Ŧ�ƭ

HEC ��t���]P?�C

n|W|�ËAđì�= 6�+Īŕ­Ë C,Ƭ4�+�ơË+�! 2�%�ƞ+ C&Ƭ1�%ěŕ H&Ƭ�>�>�ř´�$�=ƭė< 1�+�ơË,�ř´)ĵ�;>$�=(À 1a)ƭ�>; 6�+�ơË,įÐ+ C)îÕ�$�=@�%,(�Ƭ6�+ C):"$�Ċ�>$�=ƭ�+řĎƬ6�+�ơË,n|W|�Ë+x|N+ůűAŤĶ)Ü�=�&�²Š&(=ƭ�(

@!Ƭn|W|�Ë+ÌÁ�=ÚƢ,Ƭ�ơËƠ):"$÷4>�đƈ&("

$�=(À 1b)ƭ

�+�ơËƠ�Ƭn|W|+°èêAĜ7$�=ƭ�(@!ƬsEaU+

ơŨA8"�ƠAô#�&):"$Ƭn|W|,lwU+ơŨA8#EI|

A#�4 9��(=+%=ƭ

C

CC

C

CC

C

CC

C

CC

H

H

H

H H

H

H

H

H

H H

H

= =

(a) (b) (c)

= =

OH OH OH

Page 4: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

52

IC��t�[|�n�[]� C

DyJ|)e{P|A°è��=&ƬwTJy°è):"$ěŕ&e{P

|&��>Ĉ@=�&,�%)ÍB ƭ4�ƬDyO|)e{P|A°è�

�=&Ƭ�ƒř´)e{P|��§�=�&8ÍB ƭ%,Ƭn|W|)e

{P|A°è��=&'�(=+ ?��? °è+��Ă� 2Ƈ<=+%Ƭ�>�>)#�$ų$ŭ��ƭ

!�

!� !�

!�

!�!�

"� "�

"�"�

"� "�

!�

!� !�

!�

!�!�

"� "�

"�"�

"� "� #���$����

%&'� %('�

� ��������� (a)Īŕ­Ë C '��+ř´Ƭ�:.Īŕ­Ë C&ěŕ­Ë H&+ř´ƭ6�+ C& 6�+ H,µ�ÚƢ�)ÌÁ�=ƭ�,�ř´)ĵ�;>$�=ơËƬ�,�ř´)ĵ�;>$�=ơËA;@�ƭ(b)6�+�ơËAơËƠ&�$;@��ôƭn|W|�Ëx|N+ÚƢA���;ơËƠ�÷B%�=ƭ�+��+ơËƠ),´Ÿ 6�+ơË��Ċ�>$�=ƭ

CH3 HCl2

CH3 Cl + HCl

CH2 CH2Cl2 CH2 CH2

Cl Cl

Cl2 ?

Page 5: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

53

IEFC7����\RUd|�n�\bd2#� C

n|W|&Åŕ Cl2AĢ´�Ƭ��)ƕ Fe A§ $5=ƭe{P|�ƔÕ&ħ��°è�=�&,£ċ)ÍB ƭ�+°è,ĕ+¨Í°èß%;

@�>=ƭ

2Fe + 3Cl2 → 2FeCl3

�;) FeCl3,Åŕ&°èAś�=ƭ

FeCl3 + Cl2 FeCl4– + Cl+

��%ij�= Cl+�Ƭn|W|+�ơË)ùø�>=ƭ��$Ƭn|W|

�Ë�+ H&ŝ�û@=ƭ�(@!ƬƕŶÊÌÁ�)��$e{P|&n|W|&,ŝû°èAƊŭ��=ƭ

�(@!Ƭn|W|&e{P|&AƕŶÊ+ÌÁ�%°è��=&Ƭĕ+

:�(°è�Ɗŭ�=ƭ

Cl2+�@<) Br2Aĵ�>-ƬC6H5–Br�æ;>=*2ƭ

IEGCiz�l�\bd��t�_]|�n�� � C

ƕŶÊAĵ�=�&(�Ƭn|W|&e{P|&AĢ´��å)�Hcy

L~A� =&Ƭ��+:�(�§°è�ij�=ƭ��%ij�=n|W|m

KRM{x`(BHC),Ƭęū¤&�$Ƙ�ĵ�;>$��¨´Į%=ƭ

2 F2& I2+ô),Ĺ(=ĂĞ�ĵ�;>=ƭ

HC

HCCH

CH

CH

HC

Cl+HC

HCCH

CH

CH

HC

HC

HCCH

C

C

HC Cl

H

H

Cl

HC

HCCH

CH

C

HC Cl

H+

H+ + FeCl4- HCl + FeCl3

+ Cl2 +HClFe

Cl

Page 6: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

54

JEC ��t�]8��C

JEFC�3�f F ��WYa]C

n|W|)ÏŠÂA 1� �Ó���¨´Į&�$,��+:�(8+�=ƭ�>;,ªŪ½9ªĽčĀA´ì�=Ɲ+�ľčĀ&("$�=+%Ƭ

¶ŎAŴ $���ƭ

_yH|,Ē�(ĊĔ¨´ĮAĦ��Ħ¤&�$Ü�ĵ�;>$�=ƭÄ

Ā9úņ¤+ØƑ)ĵ�;>=ƭ¦Į)õÐ�>$�=ƭ_yH|AƐ¨�

=&ÎëƨƐ�æ;>=ƭÎëƨƐ+a_xFuÅ,�ÌĀ&�$ƧĀě)

ģ§�>$�=ƭkGd~y+ØũěĦĠ,ƬğĚŪ&�$ªĽĔƚ%ĵ�

;>$��ƭ¦Ū%=ƭUZz|,rxUZz|(PS)+­Ā%=ƭn|W|Uyp|ƐƬb_{n|W|ƬDbx|,Ƭ�+¨´ĮA´ì�=�7

+�ľĮž%=ƭ�& -b_{n|W|Aƌ��=&Dbx|�æ;>Ƭ

Dbx|AčĀ)DV_Dbx`A´ì%�=ƭDV_Dbx`,�£Ƭŵ

ĭƗļ¤&�$ĵ�;>$��Ū½%=ƭ

OH

SO3H NO2 NH2

COOHCH3

NHCOCH3

���� ����

��������

�����

������ ���� �����

HCCH2

����

+3Cl2

H Cl

Cl H

HClH Cl

ClHCl H

Page 7: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

55

JEGC�3�f G ����WYa]C

n|W|IJ), 2���+ÏŠÂAÓ��=�&�%�=ƭ�& -��+ªŪ½��&�$ö�;>=ƭ

RxZyƐvZy,ğĩƗļ¤R{vZ~y+�ì�%=ƭDVZyR

xZyƐ,ƥļŪDUjx|+�ì�%=ƭfkCx|+�ì�%8=ƭ

�ş&8RxZyƐ�;´ì�>=ƭ�+RxZyƐ,kGd~y�;´ì

�>=ƭ

n|W|IJ) 2�+ŝûÂAÓ��=ƝƬŝûÂ'��+ńÒŀ(�ŝƚ�� 3 gY~|ij�=ƭ�& -�CH3&–OH AÓ���ô),ĕ+:�)(=ƭ

o–Ƭm–Ƭp–,�>�>Iy_ƬvYƬgw&ź6ƭ�Qm�u��,ªĽĔ

ƚ%ğĚŪ&�$ĉƅ4%ĵ�;>$��ƭ��>8Łţ)Ŷ>=&ĩĻA

ſ��ƭ

��������� ����

O

O

CH3

���������������

OH

O OCH3

O OH

�����

OH

O OH

������

CH3

������

CH3

OH������

OH

H3C

OH

Page 8: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

56

KC/)Sc%.,9f�d�5A$��,]��C

ŧƨĄ¨´Į+É«,ňĝA­Ā)´ì�>$�=ƭňĝ�)¸4>=�

Ų(ŧƨĄ¨´Į,n|W|Ƭ_yH|ƬKSz|(o–Ƭm–Ƭp–Ĺê�+Ģ´Į)%=ƭ�>;A4&7$ BTX&º0

KEFC ��t�Scrv�yXdC

�ŝûn|W|),ƬŃú´ì%�=8+&Ƭ2 ĘƜ��+l{VUAŘ(�>-´ì%�(�8+�=ƭn|W|�;UY~_�=´ìy~_+

�A��)ŋ�ƭ

CH3 CH3

CH3

CH3

CH3

CH3

CH3

NO2 NH2 NHCOCH3

CH2CH3 HC CH2 HC CH2

n

/-:3;); #/7; #(-#5.

3;); '*9; 47'*9;

CH CH3H3C C CH3H3C

O2H

OH

1$0<8

����������!" �

���26'*+& ��

����=���!���

�� %',8�

��

���� ��

Page 9: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

57

��%´ì�>�kGd~y�;,Ƭ�;)ĕ+:�(¨´Į�´ì�>

KEGC y�i�Scrv�yXdC

�ĂƬ_yH|�;,ĕ+:�(¨´Į�´ì�>=ƭ

OH OH

COOH

OH

COOCH3

OCOCH3

COOH�� ��

�� ��� �

� ��� ������

�����

�����

CH3

COOH

CH3

CH CH3H3C

CH3

CH3C

OOH

CH3

CH3

OH

�����������

��������� �

���� ��� ��

��

Page 10: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

58

KEHCkq��Scrv�yXdC

4�Ƭp–KSz|�;,ĕ+:�(¨´Į�´ì�>=ƭ

KEIC ��t�Sc~h{��fZTdC

kGd~y,Ē�(ªŪ½9ƪ�ËčĀA´ì�=Ɲ+�ľčĀ&�$

ƒŲ(¨´Į%=ƭn|W|�;kGd~yA´ì�=Ɲ),Ƭ–OHÂAn|W|IJ)ŃúÓ��=Ñĵŀ(ĂĞ�ī��7Ƭm��*&º->=ðŮ

Aĵ�$ijĴ�>$�=ƭ

Mv|Ğ,ƪď¨Í+ÿōć)8ƃ"$�=+%Ƭ'+:�(��5)

("$�=+�ĺ¾)é"�ş8�=�& ?�ƭ��%�¿,Ƭ�+°è

+��5Aų$5:�ƭ��),Ƭ�>4%)ÍB%��ĊĔ¨Í+ŻŲŕ

�ŗ5´@�"$�=ƭ

�+°è+œ�ĘƜ,Ƭl{jz|&ƐŶÊ&+°è%=ƭ

+

OH

+O

��� ��� ����� ����

CC

H

H

H

H3CH

OH

H

H3CCH

CH3 OH

H

CH3

CH3

COOH

COOH

CC

O

O

O

CH2CH2 O

n�������� ��������

�����

�� HOCH2CH2OH

Page 11: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

59

��%ij��ƬĖơŨA8"�Ī¨ěŕ[CH3CHCH3]+EI|�Ƭn|W

|&°è�ƬMv|Aij�=ƭ

ĕ)Ƭ�+Mv|�ĭ):"$wTJyƙŰ�=ƭ��$Ɛŕ O2&°è

�=ƭ

�+�Ë� 2 �ł+Mv|&°è�$Ƭěŕ H Aà�ñ�ƭ�+ĘƜ,

wTJy°è+ƉƖ°è%=ƭ

H Aà�ñ�>��ß³Œ+wTJy,Ƭ�Ę£)í"$Ɛŕ O2&°è

�Ƭ�;)ĕ+Mv|�; HAà�ñ�ƭ�+Mv|h`{oyIKS`,H3O++þüA±�=ƭ

H3CCH

CH3CHH3C CH3

HO

H

H

CH CH3H3C

HO

H

H

���

CH

H3C

H3CCH3C

H3CH

O2

CH3C

H3CO

O

C HH3C

H3CC

H3C

H3CC

H3C

H3CO

O

+

CH3C

H3CO

OH

+

����������

Page 12: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

60

Mv|h`{oyIKS`, H+Aù4 $ H2OA�<Ɵ�ƭ�+&�):�� �ij�=*3ƭƂ�°è&,�Ë�%­Ë&­Ë+#(�<Ă�Ǩ�Ƭ

�Ë+ƩĐđƈ�Ç@=°è%=ƭ��%,n|W|IJ,ĉ ) C ­Ë&#(�"$���Ƭ����>$Ɛŕ O&#(�<Ń�$�=ƭ

ĉŖĘƜ,§ě�ŵ%=ƭ�+ĘƜ�Ŗ@=&ƬłŀĮ+kGd~y&Ƭ

¥ijìĮ+DV_|Ƭ�;)ƐŶÊ H3O+�ij�=ƭƐŶÊ H3O+,�Ɖ+°

è+ĉ +U][l)í=ƭ

3 ĊĔ¨Í°è,ŝûƬ�§ƬŢƟƬƂ�+ 4gY~|)�Ʀ%�=�&A�%)ÍB ƭ

CH3C

H3CO

OH CH3C

H3CO

OH

H

OC

H3C

H3C H

OH

OH H

H

����

����

OH H

H

OC

H3C

H3C OH

HO

CH3C

H3C O

H

H O HH

OHH3C

C

CH3

O

����

����

Page 13: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

61

LC ~h{��Sc�"Ved%.��,C

LEFC ~h{��Scp�w�>fZTdC

kGd~y�;RxZyƐA´ì�=ĂĞ&�$,Ƭo���q��xy�

&º->=ĂĞ�ĵ�;>$�=ƭ�+��5Aų$5:�ƭ4�ƬkGd~

yA NaOH&°è��Ƭa_xFukGdKS`&�=ƭ

a_xFukGdKS`A 10 MPaƬ125 °C%�Ɛ¨Īŕ CO2&°è�

�=&Ƭ–OHÂ+ o–�)��$ŝû°è�ij�=*4ƭ

RxZyƐ+a_xFuÅAƐ%�¼�=&ƬRxZyƐ�æ;>=ƭ

4 –OHÂ,Iy_}gwƎ·ê(+%Ƭp–�)��$8ŝû°è�Ɗŭ�=+%,(��&ĺ¾Aô#�8�>(�ƭ���Ƭ�+°è)��$, Na+

� CO2A o–�)Ó��7Ƭ2&B'� o–�%°è�=ƭ(�ƬNaOH+�@<) KOHAĵ�=&Ƭŝû°è, p–�%Ɗŭ�=ƭ

OH O Na

NaOH+H2O

ONa

���������

ONa

OC

O

OH

C

O

O

OH

C

O

O

Na

Na

����������

OH

C

O

O HO

H

H

OH

COOH

+H2O

�����

Page 14: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

62

LEFEFCp�w�>Scp�w�>�w�fZTdC

RxZyƐ+–COOHÂ)vZyHU]y¨Aă�$æ;>=¨´Į�RxZyƐvZy%=ƭ�+°è,�ťŀ(HU]y¨°è%=ƭ

LEFEGCp�w�>Scgsw�p�w�>fZTdC

RxZyƐ+–OH ÂAƏƐHU]y¨�=�&):"$æ;>=¨´Į

�DVZyRxZyƐ%=ƭ��%,RxZyƐADyQ~y&�$ĵ�

$�=ƭ�+°è,ƏƐ&+°è%,(�ƬīěƏƐ&+°è%=ƭ

°è,īěƏƐ&Ɛ(ĨʼnƐ)&+°è�;UY~_�=ƭʼnƐ,ŶÊ&�$�ĵ�=ƭ

��)RxZyƐ�DyQ~y&�$þü�$�=ƭ

OH

COOH CH3OH+H3O+

OH

COOCH3 + H2O

����� ����������

O CO

CH3

COCH3

H O CO

CH3

COCH3

HO CO

CH3

COCH3

H

HO C

O

CH3

CO

CH3

HO

COOH

OC

H

H3C

HO O

CCH3

OCOOH

OH

H

Page 15: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

63

LEGC ~h{��(4C

kGd~y&pyuDy^h`&AŶÊÌÁ�%ƒ´��=&ƬkGd~

yēš(n~MwE_)�æ;>=ƭkGd~yēš,§ĭ):"$Ŋ¨�=+0�!(4%=ƭÎ�%ŚŜê)�>=ƭƁƅ(&�?%,ơĤQ|V|

_)×�Ƅ6t\sY)ĵ�;>$�=Ŋ�ēš�n~MwE_%=ƭ

OC

H3C

O COOH

OC

H3C

O O

C

CH3

HOCOOH

HH2O O

C

CH3

HO

H3O+

���������

��

OC

H3C

HO O

C

CH3

OCOOH

OH

HH

OC

H3C

HO O

C

CH3

OCOOH

HH2O

OH OH

OH

Page 16: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

64

MC2#��&C

�%)n|W|IJ)Ó��>$�=ÏŠÂ�Ƭ2 �ł+ŝûÂ+Ó�)¯3�ãƣA2#��&&º0ƭ2�ł+ÏŠÂAIy_4�,gw�)Ó��=êžAj�yQ}�=�!ƬvY�)Ó��=êžA�v=�!&º0ƭĒ�

(ŝûÂ+Ǝ·êAÀ 2)ŋ��ƭ

Iy_-gwƎ·ê+ŝûÂ�Ó��>�n|W|IJ) 2 �ł+ŝûÂA

Ó��=&ƬƇÙ,Iy_�&gw��µĆ)ijì�=ƭ�+�7Ƭ�şA

�Ɵ�=ý��çŲ)(=ƭ

MEFC��,�"��y]<�C

�4�4(¨´Į�n|W|IJ)ŝûÂA 1��#Ó��$ŭ�ĂĞ%´ì�>$�=ƭ�+&�)ŝûÂAÓ��=ƤĸAŞ (�&Ƭłŀ&�$

�=đƈ+¨´ĮA´ì�=�&�%�(�ƭ

�& -n|W|�;RxZyƐA´ì�=y~_,��+(a)(;²Š �Ƭ(b)%,�²Š%=ƭ�>,Ƭ–COOH �vYƎ·êAŋ��;%

=*5ƭ

5 Iy_-gwƎ·ê(+%Ƭ(a)%,gw�)ŝûÂA8#¨´Į8´ì%��� �ƬƎ·ê&,Ĺ(=ıĶ%Ƭ�+¨´Į)ƛ"$,Iy_�AƋò

ŀ)´ì%�=ƭ

NO2

SO3H

C

CH

O

OH

OC N

N+R3 C O

O

CH3

Br

F

I

ClC CH3

O

CH3

OCH3NH2

C6H5

HN C CH3

O

OH

���� ������

� GC C2#�]�v=�!Rb^j�yD}�=�!�vYƎ·êAŋ�ŝûÂ�Ó��>$�=n|W|IJ) 2 �ł+ŝûÂAÓ��=ô),Ƭ1�ł+ŝûÂAÂĥ)vY�%ŝû°è�ij�=ƭIy_-gwƎ·ê+ŝûÂ�Ó��>$�=n|W|IJ) 2�ł+ŝûÂAÓ��=ô),Ƭ1�ł+ŝûÂAÂĥ)Iy_�&gw�%ŝû°è�ij�=ƭ

Page 17: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

65

N�@OC

(a)&(b)+'!;+´ìy~_AƋ01��¡ā�:ƭÀ 2 A®Ş)�$:�ƭ

N61OC

(1) (a) (2) (b)

OH

COOH

COOH

OH

COOH

OH

(a)

(b) �

NO2 NO2H3C

NO2H3CH3C

(a)

(b)

(a)

(b)

ClCl

Cl

(1)

(2)

O

CH3

O

CH3

O

CH3

Page 18: ベンゼン環を含む - Coocantakahiko.life.coocan.jp/univ/2012/121107_25_aromatic.pdfOH ONa NaOH +H2O ONa O Na O C O O H C O O OH C O O Na Na OH C O OH O H H OH COOH +H2O 62 LEFEFCp

66

N�@OC

(1) ĕ+¨´Į+đƈßAŹ�ƭ(a)n|W|Ƭ(b)_yH|Ƭ(c)UZz|Ƭ(d)Dbx|Ƭ(e)b_{n|W|Ƭ(f)kGd~yƬ(g)DV_Dbx`Ƭ(h)RxZyƐƬ(i)ÎëƨƐƬ(j)M{{n|W|

(2) ĕ+¨´Į+đƈßAŹ�ƭ(a) o–MzX~yƬ(b) m–MzX~yƬ(c) p–MzX~y

(3) ĕ+°è):=ijìĮ+đƈAŋ�ƭ

(4) (a)&(b)��>+´ìy~_AƋ01��ƭÀ 2A®Ş)�$:�ƭ

N61OC

(1)(2) Ņķ (3)

(4) (b)

Br2Fe

Cl2hν

(a) (b)

CHO CHO

CH3

CHO

CH3CH3

(a)

(b)

Br

+HBr(a)

H Cl

Cl H

HClH Cl

ClHCl H

(b)