Giao Trinh Hoa Huu Co Cua DH Su Pham TpHCM
Transcript of Giao Trinh Hoa Huu Co Cua DH Su Pham TpHCM
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!"##$$%#!'()*#"+,'-
./"*012'231'Cl Br
'4'4',#'4'
56(7*###$89:/&---96('; )! ? #@ ? 9: / 96 ) #!"##$A(BC-
./"*
Cl Br
ClCl
Cl
821D#',#',1E7121#'$F01',#',$-!"!#"()*+,!-#,A##C-=3G#"##$H'./"*01'012121'231'
I'#'J'#'.'#'#-!"!#",)./=3"##$4)&H$;'A)6'#KC-./"*LM1E1E1LMLM1E12E$"$7"$7
"- &0$!-1/2-3*,(-4541/N0N'O7'0'O7E0E7O70"O7'P#$#''2D#'##$678
!"#- 9:1;+,()9Q&>#;8#)#RSQT#U,
!V!&N27*';
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#-;&$%(&
HC CH
Cl
ClHC==CHCl Cl HC CHClCl2 2
2 2
+ +
"-+&(+&0!3*"=)6#?!##?!
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0RHJE00R1EH0J00RHJ00R1H0J0=)6"6+)*X2YJ(!#"96$78#6#'6J'0#6"6J'M-RHJ'MR1'HJ'0H'\=#'2)#Y&5RH'2AJ"CR1'H2H'
-*(!.**(%#!#/(!#0*1"'/2\R1HE2Y'PR1EH2HE\1RY1H2E2Y'PE1RY1EH22H2E\R1RY1HE2Y'PR1RY1EH2HE3&.*"1/.552Y',
152H52ZZ`152a'R1X$\ENP?!
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-.R1XH1R1HX1 R1XHRY1R1RYHX1
R1XH50R152HX
R1XH5R15HX/0*. -
23121X121XAC21XAC01X!#)#5"##$$$)!;)!-/0*.1# R21XRRY1XARC01XR8RY'6#4'8,#'4'---(B#)#528#6(B#)#58#6,!#!-/0*#
231XR1321X1X
@,!B(4;4T#;;(;8&?7;#)#4))#5-./"*#!&?(#&7#)#4(&-
Cl
NH
NH
Na NH2
2
23NH
_**+
_
NH
50%50%
+
33
3*
Co
OHOH
OH
NO NONO
Cl
Cl
Cl
_ _+
2 2 2
_
?567857@02
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C C XZ
O+Z C C C C +
XZ
_
[O_
] O+
Chm nhanh
123
C C XZYO +
_
Y Z C C X C C + Y
X
Z
_
_
O
[ O_]
516,
/5675&7X#6#!#$#&$;##)*4#&&7)!##$4A;&?')*C-QT#64&"*#&7,&(;!^&7*#'7---AQT#7C-
A)#(."$!&B,4C@28(-]A7FC4A?C
C C
Br
Br
CH
CH
H
HBr
Br
CH
CH
H
H
+ I-Br
H
H
CH
CH
Br
I+_
_
_
3 3
33
3
3
I
_
=AR8R>#8C4A#?C
C C
Br
Br
CH
CH
H
HBr
BrCH CH
HH
+ I-Br
H
H
CH
CH
Br
I+_
_
_
3
3 33
3
3
I
_
)#'*)!4,!#)#] #$"*6##$)($4#&&7&'67##$$-
Y C CH X C C X C C X_ _
__
YH+
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567A7BCBDEF5GB9-.+:*;#96#R8I(!&9)&"+,'7)6-0121EHI40121IE]'7$7
LM1EHI4LM1IEJ'7$7\-.+7;20121EH2U4A012C2UHUE20121EH2e40121eHeE\-.+020121H2540121210H255647'*#6#&"C(
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77
77DE
F7DF7DF7DF7D,F7D@IJ9K8B9:L23eLMIE`A0C2Ea0'0A2MC2U025A0C2`A0C0'a2A2MCPJ$LM'?F*=#)('(+'H,#
!V!&RWREWR'WWRN-RN4!&9)&e8I-6!&$c9)&RX)!"*+-
LM1EHI4LM1IEJ'7$720121EH2U4A012C2UHUE20121EH2e40121eHeE20121H250121210H2520HA25CA0C2H25#2N+( R1XHRYeR1eHRYX
Cl Br ClLiCH - CH - CH -Li
3 2 2 CH - CH - CH -Br3 2 2+
+
#)(,(+(,+
A012C2H2520125H0A0C2H'2A0C0'H0A0C2HIA0C2IH
'#"+(,++,"
RIXHJ$X2RPJ$HJ$HIX2
PLMIEH2J$'2ALMCPJ$HJ$HIE'J)&6"6(##)47#!E8'8G88='8G88J$8$8E8----
#"+(,++6'"N
RIXHRY13R1HRY13IEF#)("P'+(+0KQ
LA0C232H2'H022`A0C212a0'F$'7
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@+*="F@5:I85GF@57@GL@5:8@CBDM5:8C57@5I9N8O@5:8@I65@57@EF5GB5PJ@I6C57C57@5I9N85Q978MB9N8O@5:88PEF5GBDFR84
D!CG/"!C-#/,4C,#,!3*",!'$,39+H:3#+,#,$#,!09!#,!4
", P!"=Q" 0"@ "> " R> ", 0" @ "> " R>
R5 HH HH HH HH HH R 1 HH HH HH
Re HH HH HH HH HH R HRX HH HH HH HH HH R2U HH HH HH HRIX 1 HH HH HH HH R2" H HH HH HR2E 1 HH HH HH R2 1 1 HH 1R0' 1 HH HH HH H RPJ$ 1 1 HH 1IIJ!&)!)6SIJ!7SJ4!&)!(4)6S
KF//.=f#'=RXHIACRIXAGC
5:I8MI7@@I65GL@5:8@D5B9N2R1I1X RIHHRIX21 R2IHIX24'7'#)7D4'7I'
XRXR1II1RIIXRX
R1I1XYYR1HX1IH
#4O@5:8F75FG@--.,PS3QgHHRhXgRHXH0hIEHE1E01EHIE22312eH231210He)#]]2>#]A'#')*!^`C\J!&9)&)*##&'(;11IXRY1RY1IXXY_XY1IXR1I1XHRY1R1HRY1IX11IXRY31RY31IX251251IXRY51RY51IX
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JJ6"6(##,#'4$B9696,&,(:'(;#!#-
Br MgBr+ Mg
+ HOH+ Mg
ete khan
Br
OH\J!&9)&)*##&'-
=G#'52-JJ
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\;96(3J!&,!4&?9)&(3"/#*#?(T9)&&7&'#c#&
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2&,\A0C2H'011'HP\1212'H'1210H'2\LM'HE2LMEH'11E+(,+N(77DE
?/Ae*J1JJR0JJRM\e*J11RD+,#!,)96#!,#
P+(,+KN(Q;(-/9-,J0R1J2R1J1RR2J1R`RPJaHX1
"J$;#J$;#2J$;#0J$;#Pf#E;#9625J2HRR1J2H5RJ'2H`PaR1J2H2'R132HJ0R1AJ2C10A,,CE;#00RIXHJX0R0JH0IE'=/#e6B$F)7)&842!&9)&-`A02C0JHa'1 H' A02C0J H]1' `A02CPJHa'1='#'HE'0='#'`A02C0JHaE1'0='$#'D+$:,&:M-`a./"*02J202J3
`a 20A02C2J02J3`a 20A02C0J02J3 20
HLM1e9-ALMC0JH1ALMC0J1LMALMC0J32HALMC23
01e211LLALMC0J3HALMC232i##(B6#"6JJ6(
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9D$02MHJ'0A2MC0J3A2MC2J3 10'H5Y1]15H
/;M,PH2EA''0SMZZC2E2H22'PHP0A0CPHP''PH202A02C2'2H2'
'PHP05A0CPHP5''PH2A02C2UAPZ1LZZCA02CPH2U'2'PH2A02C2UAPZ1LZZCA02CPH2U'2'PH0I'A0CPHA0C0'HA0C2'2H0'0202I'HA0C2'2A02C2A0C2H2I'220'H2IH'PA0C2'2H2I'220'HA0C2'22&,.)&,''0>#N'0()*#?!
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!-3/
LGI2LMN(1/)',!%5##H#'C
0121#''#A]'#'CS 012121#''#A'#'CS01A2C01#'$'#A$'#'C-\=)696!;()*#'"6-23121A0C01LM12112121#'''##'1$'##'$F'#]''#'121AC121G','A0C21A0C2J#'
4/*.44P5C9=!,?O#((Y;(;"$&A&^-I#--CR132HA2P((YZCR1AC0
R132-E2LS2--22R12121
4'6GL@5:8@5@?FJEU5QB8@5@?FQBEB@A5PV5WQI5:84R13H`2aR1214!2Y5Se'PSA0lFC0'RRY3H`2aR1ACRY2#4!?B(3RH`PaR2H,"6e'PRRYH`PaR2HRY]?"65Y'RXH`PaR2HX,"6e'P
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4PGL@5:8@D5B9N-RIXH2RIXH2RHXIRIXHR2IXRHXIRIXH212R212IXR2121HXIH#'$;#RIXHRYRRY1IXRRY1HXI
""84'#!,'#'$;#2#6,96?##'$;#0-7(##'$;#0#&(;c"6#)e96,#&(;-
CH
CHCH Li
CH
CH
CH C
CH
CH
CH
CH
CH C CH
CH
CH
OH
CHCH CH
CH
O3
3
3
3
3
3
3
3 3
3 3
3+
Izopropyl liti Diizopropylxeton Triizopropylcacbinol
56#)#T)!;(;)68/#9;'&V4RV96V-./"*;(;!8;(;&)V#6(;96)!7-5'6"*'4'!8#B'67#/#9;'&(#)*#*##&B7#&
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=#!##'47'*47('6#T;(;#&4&'!76!"&'6B#-D+$:!"":##&/$F7*-R5HRH5F7DE5GB=/,W0W2MWA0C2WA0C0=/$F1b01b2M1bA0C21bA0C01
489S9X89F75Y]&RHRY RRYHXP((YPZZ
$Y]?&RHRY RRYHXP((YZ
RXHRY RRYHXXP((YZ
ARC2HRY RRYHRX"
R2'HRY R2RYH'XP
5,9#)*?9#)-RHX RXHXU'2
=#!e#A'YU'2C#@#'$;#0'61$'#'#!&*?!1$'#'-#'$;#2!&)#6#'$;#-5'6#'$;##6#/$F#67*-0C01H'YAU'2C A0C01'H2&
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#' 4 #B #& 4! V #
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?#!'#B$()*#(# 2296###'8,)&>##?PA=4
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2121H1A1212111CH2\J!&,&,&''#'$)!50((?!
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CH
C C
OH OH
CHH
CH
C
OH
C
OH
CH CH
C C
CH
C
O H
C
CH
CHCH
CH
C C
OH
OH
H
O
O
OO
O
_
+
++
+
2
2
+
_ +O
6 66 66 6
66
6
6
5 55 5
5
55
55
5
H H H H H H
H
H
H
H
CH
C C
OH OH
CHH
CH
C
OH
C
OH
CH CH
C C
CH
C
O H
C
CH
CHCH
CH
C C
OH
O
H
H
O
O
OO
O
_
+
++
+
2
2
+
_ +O
6 66 66 6
66
6
6
6
5 55 5
5
55
55
5
CH
CH
CHCH
CH
CH
CH
CH CH
CH
6 6 6
6
6 6
6
6
6
65 5 5
5
5
5
5
5
5 5
4C58MBFEA5P@57@8MBFEC57@YG'#'e6#'!?&8476#&9:*8?)!2pZZ96((>#)!lZ-
1f#
CH CH
CHCH
CH
CH CH
CH
CH CH
CH
CHCl
Cl
Cl
OH OH
OH
OH
HO HOCl Cl400oC
3 2 2
2
2 22
2
2
2
2 2+;
CHCH
CH
CH
CH
CH
CHCH
CH
CH
OH
OHOH
OH
HOC22
2
2
2
2
22
2
2 2
CH
H O
H
Ni
Al(OR)
C H OH
H O
OH
OH
3
5
O
2
1=/#=)*''#'#@#&!&&"*?
21AC12D"&231H221AC12H050((Y2P((2521A52C1252H0G'#'#&&"*#;#B#;#?#!#)6-
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$Y]'e6#T#&9:*()*#)-&(A7FC96AD8eC1f#\IF1'
CH
CH
CH
CH
CH
CH
CH CH
CH
CHOH
OH
2
2
2
2
2
2
2 2
22
2
CH
H O
H
OH
OH
3
O2
Br
Br COCH COCHO
OCOCH OCOCHC CH
CH
CH
CH
Br
Br
CH
CH
CH CH
CHCH
CH
CHOCOCH
OCOCH
OCOCH
OCOCH2
2
2
2233
3
3
3 3
3
3BrBr
AgOCOCH AgOCOCH+
+
+ +
+ 4
\D8e1]'
CH
CH
CH
CH
CH
CH
CH CH
CH
CH OH
OH
2
2
2
2
2
2
2
2
CH
H O
H
OH
OH
O
2
Br
Br
O
C CH
CH
CH
CHBr
Br
CH
CH
CH
CH2
2
2
Br+ +
+
+4KMnOKOH
H
OH
OH
O
2
=
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4"5WQI5:8JVMFQB@I659R85RLGLAFP8D-G*#Y=79:B_'96"##$-$Y='6"+,96)*#&&7-
OH
OH12
4
OH
12
12 3
4
56
//
HO
HO
HO
1//1 2
a/ p-Terphenyl-2-ol a/ Biphenyl-2,4,4,6-tetrol/
b/ 2,5-Diphenylphenol b/ (p-Hydroxiphenyl)phlorogluxinol b/ 2-Phenyl-1-naptola/ khong^
/
4*=MF@FNB9RLY#*(&'?4$*#)*#4-$Y5#!,?O#9)&$F47-
LM105H5LM1H520#YJ)&R?#-EF8'9644/)!)&4/(^(!-LLH'HY22LM1'HLM1'HLM1H'"Y,((j#!$F-#-
C
CH
CH
H C O OH C
CH
CH
OH
O
CH
CH
3
33
3
3
3O2 100oC+
Cumen Cumen-hydropeoxit Phenol Axeton 5)6#E2C
OHO
2Br
HBr
2
4
+
-Menton ( 3-Oxo-p-mentan) (1-Metyl-4-izopropylphenol)
Timol
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4+O5QB8UL567@5Z8[78EB9NC9:8\-LM11 LM11HH
Y=*'LM11H5 LM115HH2D":#'#"-LM1H'1RA"CLM11RH'LM1HA0C2LM110H0?$&96)7)64$4#&,`(;"+$:#
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$Y=$)!&77J'44''*!&9)&5P0Y50((-J!&E4)-
OH3
/
2NH HSO NH4
Noi hap 150oC-
2-Naptol 2-Naptylamin #Y=$)!J!@,!9)Y4!7*';##9)&$;4B7-LM1HUPZZLLHU
456765N8D;0M24Y'&J!&"+"6#&44#,`#&
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OH
3_
22 2+ CH =CH-CH -O-SO Ar
HO
CH =CH-CH
ArSO H( orto; para)-AlylphenolAlyl arensufonat
5"6#'HEN0c?!#7'#96A7FC##-
O
O
OHH
(CH )C (CH )
(CH )
(CH )(CH )
(CH ) (CH )
(CH ) (CH )C
CC
C
C
CC
C C(CH )
(CH )C
(CH )C
O OO
H
3
3
3
33
3
3
3
33
333
3
333
3
3
3
33
3
3
[ O ]
Do,_( )
PbO
C H6 6
_H
O
HO
OH
HO
OH
HH
COOH
HO
Axit mezotactricAxit maleic
CC
CC
C
C
O H
H
COOH
COOHCOOH
KMnO KMnOKMnO44 4
Axit oxalic Phenol
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4*#]*
HO
OH
HO
OH
HO
CH3 OH
OH
OH OH
OH
OH
Phenol (or, m, p-) Crezol Timol Cacvacrol Catechol Rezoxinol
OH
OH
OH
OH OH
OH
OH
OH
OH
OHOH
Hydroquinon
Pirogalol Hydroxihydroquinon Phloroyluxinol 1-naptol 2-naptol
HO
C
C
C C
C H
C H
C H
C H
HO
OHH
H
5
5
5
5
2
2
2
2
OH
Antranol Hexestrol Stinbestrol \(#8/#&*#96#(>#/?'&?&8#"*#!####&7#';74!4-UUFF=)',!%5
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'121_22__0801],1217',_220>#21I'1801,,1'12801,
>#*":96-
3
O
CO
CH
CHCH CHCH
O
2222
3
H C
Oxolan
(Tetrahydrofuran) Oxiran 2-Etyl-2-metyloxyran
(1,2-Epoxi-2-metylbutan)
(2-Metyl-1,2-epoxibutan)
-9N8PDFR8XF:989[G@*EIVIP=
O-CH
O-C H
O-CH
O-CH
CH=CH-CH CH =CH-CH
OH
3
3
3
3
22 5
Anisole
Phenetole
AnetoleEugenol
2
4*=4P5@FER1HRY1R11RYH2,20S2P((Y#
HO-C H3
2 2 5 2
O2
22
Oxolan
(Tetrahydrofuran)
C H-OH5
+ C H - O - C H +55
Al OHO+
2
to cao
;
OHOH + H O
H SO42
to cao
H O
4L57L*JEB9NDQ#'HR1XX'8#,##)---
Br-C H2 2 5 2 2C H-ONa
5+ C H - O - C H +
55NaBr
-O-Na I- - O -NaI
+ +
-
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59:/#Rc#
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)#7)!965,! 7 )6,>#$F-5', c5(B-#6',c52-
O2
+
+2+
+OO
H
Br_
OH
OH C
O
CH H
2
H C C H Br
SN
C C
H
H H
H
3
O
CH
2 2
3
H C
+
5+CH
CH53
++
+
O OO
H
OHO
C
O
CH H
2
2
CH C HC C
HH H
H
CH3
CH
OH
C H
HO-C H
_HO
5[-="OA=NC
e6"7"+
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)X
7JJ=1e6)*#B#)#&&7##$'"+,"##$762#6$)!7;!-
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22
22
CH -CHOCH -[CH ] -CHO
CH -[CH ] -CHO
4
4
2
*(1-Naphtyl)axetaldehyt
**Naphtalen-1-axetandehyt
*6,6-(1,4-Xiclohexylen)dihexanal
**Xiclohexan-1,4-dihexanal 5F!-C/5&!%$H1;+$$-3/-#/,)#$&0$!-31/==3"H,)&>#3#,H(-"O7# N7"01111111111,#,"021111#J"0`2a21111$#E" @=F!"!#"$!%$!&'=&0VWP$
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T&$&=)*#233*'6,84()*#"+,#&2#*-\D&9)'6,-\\D&$c)6#!,-
CH CH CH CH
CH CH CH CH -C=C=OCH=C=O =C=O222
2 223
3
* Dibutylxeten; ** 2-Butylhex-1-en-1-on * Phenylxeten ** Xiclohexylidenmetanon =&!"#=54QJF75JVMF@5@?F=4884----
CH
CH -CH
CHO
C-CH
O
OCo
2
+O
2[O]
2[O]
CrO Cl
MnO /H SO
hay CrO /H SO
22
2
2
2
4
4
4
3
3
2
2
3
O
H O
H O
H O
+
+
+
++
+2
2
2
3
to
to
Axetophenon
Tetralin Tetralon
CH ONO
HCHO H O600-700 C
2 2
o
+ +
CH =CH
CHO
O
O2
+[Co(CO) ]
ZnCl
PdCl /CuCl
2
22
2
24
3
3
2
2
3
OH O
+
+
+
+
22
2
3CH
O
CH CHO
2
2o
+
+
50 C
C=CH
R
R
R
R
R RR
R
RO
O
C CH -C-
O
1
11
22
233 3
R-CH=CH CO H RCH CH CHO R-CH-CHO ?PL567@FR7@A5PF5CB
O
HgSO / H
2
224
3
O
H O
+
+
toO
CH CHO
+
C=CH
3R-CH=CH H R-C- CH
H
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@6Y=\G7'-
22
H O ++ O22
R
R RR
R R
OO
C C
111
2 2H
OH
C
X
X OH
HO-
\\,&1=!"+,7'#"-
CH Cl CHO +2H O
22
HClMnO,
K6Y=,&""-,&""&-"XR121HACR13HH2
R121HA0ZZCR13H2ARC21HARC23HH25'6,,#Y,#',#'78c#'$;##&3c3$B6-R131R1R131R35,&'65PJ$A0CPc9#"'B'41#)*###$'#&?##$!)-
C C
OH OH
NaIO C=O O=CR
R R
R
R
RR
R
NaIO H O1
12
2
33
444 4 2
+ + + +
T6YWY=
5B9R8L5N=\J)&J-ARC2RR3H0
+
CH
CH
C
C
O
O
O
O
Ca C O CaCO2
2
3
to
\J)&$-=7$%,##$,'#9)&,'6,47'*I8=---)!;(;0ZZ(PZZ-5#&,O7#c"-
-
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34
200110H2H20H01H2H2?'6F75@EF@I55QB8UB8MBEU5DBV85P5V9J8=.)&,!&'6e'P8e'A11EC0>#2YJ""64!#"+,#',P-.+R'Q#
LM12'H2LM2H'L15A0C2LM22.'H,+R:$J
RIXH12M-----RH2MHIXACRIXH1A2MC0-----RHIXACRIXHRY1'-----RRYHIX'RIXHRY15-----RRYHIXACZ8678=
5L57L5889MD5='F@0`a,24bFMDBF755M9#H''H'
3
3+ +CH C O3
Cl
H
CH CHO HCl
AlCl
?L57L5889MD5J5H''35
H O
3 32+ +
+OCH
OC
23
Cl
H
CH O CHO
HCl
ZnCl
CH O CH=NH
HAnizol Anizaldehyd
NH NH3_ +
@L57L9BD9M=B9D5J=*#4'))&'0Y18?!
-
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X$F
CH - C - CH CH - CH=CH3 3 2HOO
H
O
CH - C - CHH O
O
+O
_H O2
[ ]3+
CH =C-CH
OH
3- O
2
OH
_
2 22
O
O_
_
=*# ;7 (B #& 7 4 $ ( c " ":# H ># 1 )* ###$'^*?B$:&AR#7#C-
C - C - CH C=C
3 3H
O
C - C - CH
O 3
OH
3
HCH
CH
C H 3
3
56CH
C HC H
CH6
6 55
* *
(R)-3-Phenylbutan-2-on (S)-3-Phenylbutan-2-on/67&767)6,8$F#)*###$'#& "+
$)!'- 5 '6 7' , 7 )6 47 ' & * '6 ! &'O7-
C - CH 3
3 2
HOO
O+O
+
+_
3 +3O+ 2
OO_
C H 356 C H6 5
Br
BrCHBrC4
H O
K68^VLMFKcI5783Hg_XHX
2N$/ZJ"/>"8"/08"/S>@08;/R8:/R-@9:5')*!8(*8?!
-
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37
e;#6';
-
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38
;#,'96,')6##'964#!'-
+O CHCH
3
33
3OH
OCH
OCH o
1-Metoxyxiclohexen
t
]6$7)647"+$:!7)6,-
+
+ +O
O
O CHCH 33OHH O
H
Xiclohexanon2
d5678MIPGL@,!)!7;?"496-
3H C=O
2 O O
O
3CH -CH=O
O
O O
CHCH
CH3
33
3Trioxymetylen Parandehyd
)!*&"":#O#7'#$F-
C O CO
_
+
+C
O
O
N-YO
H O
OHH
2
:NH - Y
NH YNHY
2
2 Imin
./"*1.)&50
C O _+
C N
CHCHCHCH
CH
CH 33
3 33
3
3
H O
OH
H
HHH
:NH
NH2 2
N
N N
H
HH
Axetaldehyt-amoniac
Trime hoa/
C O _ ++
C
N
NN
N
+ 2HCHO
3
H O
OH
2H OH
H
H HH
:NH
NH2 2
HH
Axetaldehyt-amoniac
Tetrame hoa/
N
2
Urotropin 4#"*9)&50Y0##
-
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39
+ +
N
N
NCH COOH3
333HNO :NH
NUrotropin
3HCHO +
NO
NOO NN
N
N
Hexogen22
2
1.)&R52A7C*F7'6"+,7$F#OO-LM1H251LMLM1351LMH2EF'"'
_+
CH
CH CH3
3
3
3
3 3H O3CH NH
2
Trime hoa/
2
3HCHON
N
N2 3CH = N - CH
1 .)& 251A",'7C- !
-
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+,J/$
H C - CH=O2
O
O
O
O 3
33CH -CH=OH -CH - CH - C - CH
OH
2CH =C-CHOH
CH=O CH - OH
H
H
2 2
2
+
+H
H
O
O+
+
_ HO+
"
CH - CH - C - CH
OH OHO
+
+
_H
/$
CH - C -CH -H CH - C - CH
CH=O CH - CH - C - CH CH - CH - C - CH
OH
O
O
H O_ 22
2
2
2
3 3
33
OH
ROH
RO
O
_OO
O
OO_ _
O_
+
9
CH = CH - C - CHCH - CH - C - CHOH
O
O
H O2
23 3
OH O
O
_
+H
+,1$P"YQ#)#]^##$#-
- CH - CH -CH=O - CH - CH -CH=O - CH - CH-CHO - CH=CH -CHO
O
O
OH OH H O
H
H
+
+
+
+
O
O_
_
+
2
2 2
2 HCacbocation andehyt xinamic
1$#)#]#$A#$##$C(^##$-
- CH - CH -CH=O - CH - CH -CH=O - CH=CH -CHO
O O
OH OHH O
O__+
2H Cacbanion andehyt xinamic
HO
_
__
HO
?.FR8XF:L567[B9Re\5&77'*(;'6496c?!
-
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O
O
+
2
2
HO
CHO O=
(100%
(76%
NaOH/H O
25 C, 4h
NaOH/H O
25 C, 10h \J!&B"96,-3")(;),596"-
CH -CH=O CH - C -CH CH - CH - CH - C -CH CH - CH=CH -C - CHO OOH
H OO
+_
2
23 33 3 3 33
\J!&
-
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H - CH=CH - CH - CH=O
H O
H
+O
2
2
2
3
3
3
3toCH - CH - CH - CH - CH OH
CH - CH=CH - CH - CH OH
222
2
2Ni ,
LiAlH4
Ete.. .
Pent-1-ol
Peta-3-en-1-ol
\!&7362-=HP`a3121H2
1 J!&i'OO1?-=#'6"FY$F-
O
2 2 22HO
_C H OH t o2
2
2
2 2 2C=O + H N-NH C=N-NH R - CH - R + N + H O
R
R
R
R
11
1...
Hydrazin Hydrazon
5
1 J!&'77?-+1U96"":#'-
C=O
C H
CH4[H]
Zn-Hg
HCl
C H CH CH H O+ 2 2
3
35
5
6
6
+
1J!&4!9)&,'-G(*((&968(*?4!&$)!5-
C=OC H
CHC H CH CH
H O+
2
2
233
35
5 5
6
6 6 +CH
CHS
SC
C H
CH
2
2
2
2
CH
CH
SH
SH
22
2
H
Ni
CH
CH
HS
HS+_
Axetophenon
?567FQJF75=fV9J8-D+$:,&$)!,&*,)&-1=#!='-RH`A50C2aHRH
1=#!J'-RH`A#Ca21RH21=#!E"#-RH`A,Ca21RH2=#!=',&()*#"96)7#62H#@,&"-1244/-2RH2A44YI2HY;(;C2R
-
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f%98FR4&,&(6!,&7*(##"4#&!&*,&4!*#'967-HH10H1
HLMH1LM2H1
_
2 22
+
CHO CH OH COOCOOH
KOH 50% H
H O
+
+
OO
1 567BX9CF 2
3
33 33CH CHO + CH CHO CH COOCH CH
Al(OEt)
J567?9^FBF75GB"4#&9)&,3
_
2
OOH
CHO CH - C
Benzoin
CNO
_687=
\J!&$%'-01HX2X21HX\J!!96)7-&!&96(:)&7-
22
2
CHO H O+CHO
O N
HNO / H SO43
-
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44
WE^`\ 4 bFMD5EV9J8 V (1 ,!'$ 9!S $ !+&a4 $#$F'#'-"*
-
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CC
CH
CH
O
O
CH
C
O
C
O
CH
O O
OO
OH
CH
CH
HO
CH
CH
HOO HO
O
2H O2_
__
3
3
3
33
33
3
2,3-Dimetylbenzoquinon -.6I#
C CCHCH O
O
CH
C
O
C O
CH
O
OO
OOH
CH CHHO
CHCH
O
O +H O2
__
_
C C C C
OH
_
OH
O_5
5
5
5
5
5
5
56
66
6 6
6 6
6
+ OHOH
*#
-
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@7?KJ 5 5 :I 8 5 GF=5&77'B&7,#&(;*(;&*##"+*964&';#&-J128P1"*"*#$%,_'8(&"*'$)#7[Md"*'4;!-
CH - C - CH - C - CH
OO O
OH
33 2 33CH - C=CH - C - CH
Dang xeton Dang enol
O
CH
3 33 3C C
O
H OO
CC
CHCH
CHC
H
.
C
H
H
?F758OA5P7VIG=J!&4'&6"*'#&
-
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47
!-3/
LM
_g5=e6)*#B#)#@#&&7#,##$,'#AC-5NEF5GB-=3*'6,()#S32)!'*'6,(#-$-=#R5&7###$''49)R'*6c*,(&-002,()#*#)!-23121S0131,()#/(7*#)-!1121,(#*#)!-23AC2131,(#/(7*#)!-
COOH COOH
COOH
HOOCAxit thom
,
8=44"5L57L5QB8[@7@A5PVB5QB8D5G@C&0V;+$I%5
-
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,4F5PBM5DFR8XF:V5L57L8P[G@*EIVIP
D644#&&7,O7#31,'#02,#230C,7#'#0`2a2,$#1,,'#
A0C2,F$#`2a0,'#0`2aP,7#`2aP,"#0`2aL,?#LM3,X7#
D64#&>#4#&&70,,#AUC3,7'#23,#'#A]C3,O7#2,7'#11LP1,'#22,?#,#711LP1,F'#LM1,$F#11LP1,'#56#67;?,4--- -49NF:@F758M_85GF8PA5P85GF87F7D# &0/)',V&0;+$U+,I%(L!%)%(M!%#,O);%(+,J%(+,I%(011,'01`2aM11'11`2a[11D#"'1121I''
C
O
C CH CH CH CH C
C OO
O
22 2
Xiclohexancacbonyl Butan-1,2,4-tricacbonyl
= 4QJF75@57@@5:8hI@@F7XF:FQJF7585:L>#Y"##$-14,&$%244/9)&,I*,/-14,&$%IP822lYH8---*+)*2,"#T(&31#&7*#&,&$%IP822lYH8---*+)*#,)7-
C C
2
2 2CH - CH - RCOOH R-COOH + H O
KMnO+
4
R
R
R-COOH R-COOHKMnO
H SO
4
4
+
2
H
H"
"
-
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$Y=6#'>#)*###$'-#'$;##,#6#'$;##,*##,-
C CH CH CHCH C
O
2
2
2
R- CH -OH
COOH
R-COOH
+R R
R-CHO
R - COOH +2H
""
[O] [O]
OH
RR[O] R - CH -
R - CH - COOHR - COOH"
"
2
[O]
[O]
2
2Ancol bc I
Ancol bc II
4I6JL5N@57@V5WQI5:85QB8#26KR>ZPZJ"8>R8>>R80"8"0R
###Q#
RgH2AXH>#1CR1Hg1./"*02MH505H2M
#26K+(,R/0#-.6+#R15H2R1H50#26K'H,6R/$@-.+#
R1'0H22R1H0'R1A2MC0H22R1H02M 4589NDDFR8F7DA5P@5:89Y##2.R$+:0P:(MQ# R5HI5ACR5A2CR
52YH01'050#2.R:$R+>-2RIXH2RIXRHXIR'H2ReRHe#2.R>0+>-5H5R5HR5R'#2.+-1H'231'1#6A"6(#,#&W2C-X-5ACP2HY2-2232HH20121032HH2A0C21F#-.+*AJ)&7'C-RXH2A2MC2R1A2MC2R12-*"*#!&J48'$17---HA0C2131H0
-
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J> 4*
-
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O
H 23
COOH COOH COOH COOHCOOH
CH OH Cl NO
+I, H +R > -I -I > +R -I, -R
pKa 4,2 4,37 4,54 3,98 3,43 92'(+(886',6,+#
RH5R5H2 2RHIARC2H2 RH5R5H2 2RH5202R5H2H2\2'(+'(66# RH252R0H52
R C O
O
H CH =N=N:
_O O+
+2
CH - N N:O+
3
R C O
O
O_
R C N
O
OCH3 2+
4(&.#!L!&',)./9!-CM
R C O
O
HO+
R C O
O
O_
H J!#'96#!&73?(!&79c'6g#&7-+,
R C O
O
H
_O O
+R C O
O
O_
R C
OH
Y
Y
YHO
__
ANE
5567@FRIEE9FLB024X$F8>#,-
\-.+ -0H50015PHD)&"*#!;PH052H27,,7"#)*-
R C O
O
H
O
O
+
+
2
O
3
R C O
O
O_
R C N
O
3 2
+H
H O__
ANE
NH"
NH
H
NH
2O
R C H
O
2
-
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\-.-X,9#)-J!&;:#Y;(;-&
-
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5#R#&&7&'#c4!V"##$#'"+"6-/9c9;##4&*#;!&-
HCOOH H CO2 2
Tia tu ngoai
Os
,,
+
HCOOH H CO2 +
H SO
42
dd 04&$:;)9c9;)66;7)!;(;#96)6#,-
CH COONa 2+4 3
+ NaOH CH Na COto
I$*#"+$:;)8#)##*"AJ!&?"#4C-
C H -CH -COOAg + BrCCl
76oC
C H -CH - Br CO AgBr6 5 56
42 2 + +22
&
-
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R - CH - CH - COOH R - C - CH - COOH2 2 2O
+ H O2
[O]
menAxit--oxo cacboxylic
2
1X'62*,1,##$,'#-
R - CH - CH - COOH R - CH - C - COOH2 2 2O
+ H O2
[O]
Axit--oxo cacboxylic
2
SeO2
9-."J
=6(4;!&76?!
-
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CH =CH - CH -Cl CH =CH - CH -CN CH =CH - CH - COOHCuCN dd HCl
to2 2 2 2 2 2
Axit butan-3-enoic #2"$/-
CH [CH ] - CH -COOH2
2
CH
CH [CH ] CBr- COBr
CH
CH [CH ] CBr- COOCH
[CH ] COK [CH ] COH Quinolin 160-170oC
CH [CH ] - C -COOC[CH ] CH [CH ] CH=C - COOCH
CH
CH
dd KOH dd KOH
HO+ HO+
CH [CH ] - C - COOH
CH
CH [CH ] -CH=C- COOH
CH
3
3 3
3 3
3
2
2 2
2
2
99 9
8
8
CH
3
33
3
3 9
9
3
3
3 33
22
2
3
3
3
3
3
3
.......... .............
PBr
Br
CH OH
Axit 2-decyl propenoic Axit 2-metyldodecan-2-enoic @#M,.6 -
CH =CH - CH CH =CH - CN
2
2 2 22oC
HO+
3
3
3
2
22
2
3 + O 2NH+ + 6H O
CH =CH - CN+
2H OCH =CH - COOH + NH
450
Xuc tac/ /
C#2..(K ,'#l00---8>4OCFNF-231HE2E21E1 4O5QB8-1=/,7*),)&"#&;&_#!J96J2-02b231b 1P8[lAHCP82MA18HRC8[PA18HRC
1.:/(96$)!9:/8;)!")AHRC/,!7-23121W0131W021.:/()!9:/8 #&(#?8?c/,#?W?-D;&4,(
-
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C C
CH COOH
H H
C C
COOH
CH
H
H
3
3
>
..........
........
.....
1$F')**'4(:'67/,V)!#96))!#2#!,7'#A#?C?9)&,O7#A?C-
C C
COOH
H H
C C
HOOC
H
H
...
_ O+ C C
OOHO
OO
_
H
1f&96*'#4*96M8L#*-
CHH
3_
O +O
OH
O
OO
_H
CH =CH -CH -CH -COOH
"
++
H O2
CH+
Valerolacton
2 2 2 O3
68U45:I85GFU89NFGBA5PB578M_L'5DFR8XF:5QB8cI58MFGD/#^*96
-
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HOOC
COOH HOOC
COOH
Axit phtalic[ 1,2-benzendicacboxylic]
Axit izophtalic[ 1,3-benzendicacboxylic]
pK1&2
COOHCOOH
Axit terephtalic[ 1,4-benzendicacboxylic]
2,58 5,62 4F758O_","#&7!)!'+/,7*)7,-=/,!7"4#,##,-
_ D,#&4!V*796?7;#>##!#-
COOH
COOHCOOH
COOH COOK
COOK
COOC H
COOC H2
2
5
5
COOK
COOC H2 5
KOH KOH
H O
H O
H O
C H OHC H OH
2
2
2
2
2
25 5
H O_
__
_
,,'#96,7'#"+$:"##$,'*,()#-_H2_2_0_H2,7'#96?7'#&&7 2*(;$:4'&$)!RX84!96"##$,'#,7##$,'#V2##$?9)&RX-5671"'!&9)&')*"#?B()*#",VP##$-
H
2
2 52
C H Br
2
2
22
2
2
5
_H C
C O
OEt
C O
OEt
Na(EtONa)
_ OH+
HC
C
C
O
O
OEt
OEt
O_
Br O_ CH -CH -CH
COOEt
COOEt
CH -CH -CH
COONa
COONaCH - CH - CH -COOH
dd +2NaOH _ C H OH
t o
_CO
t,O+
3
3
3
D,"+*"96-
COOH
COOH
C2
2 C22 2
2
_
o
_
tCH
CH
COOH
COOH
CH
CH
C
O
C
O
O
H O H O
O
O
Oto
;
Ahydrit succ inicAnhydrit phtalic
-
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8
")%**(%#%!&78#!3>##!#!,##$,'#$%B&74?B()*#"+,)!&7##!,##$,'#-./"*$%g-
_+
_
_C
O
C
OO
O
OHR
R Y
Y
HO
('67;?"+,^*-=(&g'6 'AXCRX ', RYR1RY ", RYRRY ]? 5285RR1528R5R 7"967" 51R51 ,",7#
5152R5152 "F 50R50 F 1R11 J,, =#!3$%&7#`$%5>#&7#&5,-
C C2 2 CCC C OOHR R
NH NH
NH
N-OH
NH
NR
Cl NR
RR R R C
Axit hydroxycinic Amidin Amidoxim Imido clorua Nitril Xeten
*%UU.)&XN8'8E8-49NFGBJ2K[2KP/Y66QY"Y '02ME0lNN7'#','"J'$7E'O'I'#']'"J'$7E'O'
4B9YI@9:Y"6'#
RCOOH R - C - Cl
POCl
SO
CO
HClPCl
SOCl
COCl
5
3
2
22
2 HCl
HCl
O
+
+
+
+
-
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2N.O+#
R - C - Cl
HCl
HCl
O
+ +
++
HBr
HI
R - C - Br
R - C - I
O
O
RCOOH R - C - Cl22 2H O
O
+++
C
C
O
O
OC
C
O
O
Cl
Cl
4O@5:8JD#*#&?*#;)!!-
O+
O
C C
O O
Cl ClR R
_
"
" :
=/#&*#(>#?-.6#)##;5#'A5C
33
22
22
2H O
+O O
C
O
ClR
"
"
"
HOR
HOAr
NaOOCR
H-NH
H-NR
NaN
_
RCOOH
RCOOR"
RCOOAr
RCOOCOR"
RCO-NH
RCO-NR"
RCON
+
+
+
+
+
+
+
HCl
HCl
HCl
NaCl
HCl
HCl
NaCl
+(+(#)##;#'A5C-
3 3
+ OOC C
C
OO
ClR R"
"
+
R
R
R1/R"MgBr
2/H O
1/ R"MgBr
2/ H OR"
OH
!V!& RNWR'WREWR5"?$;(;7(;96$&4/!#';&4-
-
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-..#
2 2C C
C
OO
ClR R
R OH
H
Pd
H
Pd
HH
H 5#@"6)!(**"c!"6#(;#9)&J"E
P9)&7;/$;
' 6 A J) & R?7C ># "6 # 4! 4 e8 11$,7"-6e'P965EP#)'-=)6)*4!#',$%+()*#?#!('96B(4;/#)*#&
-
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Y=6,##$,'#9)'-f'6)&^*8()*#&"*;B-e6!&;:#9)&,'6,-
RHRY RRYH2
CH -COOH + CH - CH -OH CH -COOCH -CH + H O Kcb
Kcb=[CH COOCH CH ][H O]
[CH COOH][CH CH OH]
3
3
33
3
33
3
2
2
22
2
2
2
= 4
H SO4
4O@5:8
-
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#@/-.++(,+#=*#'$;#-
R C
O
O R
R
R
CR
+ +
,
, 22 R-MgX
C
R
R
R OHMgXO
""
""
"
ROMgX
H O
HO-Mg-X_ _
#C/-..#.)#9)&,e' P8---76#6$:4!$)!5Y#'82Y$7>(#7#96*#'$;#A?9),C-
R C
O
O R CR OH ++ ,, 2
R OH
H
H
C H OHNa 5
?5676F7DD98JE9F5G8[FR4
#4/-..( -#&5>##'!?**6?#!,1,##$,'#-
R - C - OC H
O
H - CH - C - OC H
O
C H -ONa
R - C - CH - COOC H + C H -OH
O
2 2 2 25 5 55
522
2+
) # ! & * 6 ) * ! & "' & )* # ##$' #& &77'*(;-#!(#& c()*#+)*?!!7#6#@#&7;?#c#@7;?!
-
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WLM@49NFGB
-
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OR- C
O
OO
OO
2R-COO-
H OCOR
+ RCOOOH
HO
_
_
_ _
...
-.-#
'$F'""*9)&",#,()*#,,7#-
323
3+ +CHO (CH O) O
CH COONa
CH COOHCH = CH - COOH
-.S3PAQ
C
C
O
O
O
C
COOH
O
C
C
O
O
+
AlCl H SO
_H O2
23 4
"'#,11$F'$F#^
C
CO
O
O
C
C
O
O
+ZnCl H SO
_ H O2
2 4
OH
2
2
HO OH
,
Phenolphtalein
WE)6N.+(T8TT8TTT#R__527$;#AR_C257$;#AR_C057$;#
49NFGB@#&7$;##&&"**#-=*#!7()*#*,)&$!6,969:B#B#37-020252=)6JA-=JA-
-
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()*#(#67#A>#78C9)&,8',8?8---56#6()*#(#$%#77646605PA22ZC052H2A0C0_5H2A0C0_524O@5:8