Ue RICUACPA (Aldol condensation): [HS '08, 09, "10] a-H 9AI T

UGRR oR R , $tRE [NaOH, Na^COa, Ba(OH), 9J] Te

OH
2CH--H HNaOH HC-C- H,- -H
H
3-RyT0DFTTI (TJTTU)
C
OH O
HC-C-CH+H-CH,--C-CH3 Ba(OH)
, H,C--CH2-C-CH,
CH3 4-2RY 44

OH
HC-CH-CH,CHO H,A
H,O
HC-CH=CH-CHO +H,O
CSFTCDTToRRU
OH H O
CH
HC-c-H--CH H, H,O
A
HC-=CH-COCH +H,O
CH3

HC-C-H+H--H TNaOH
HO-H,-CH-C-H
B-RaSnf1eATifarR
O O
NaOHH
H,C--CH3+H-C-H
HC-CH,-H^-OH
4-RRYGOM-2-6

ATT-5 FR (Arndt-Eistert synthesis): e ojiUTT PCl55

1 1 SOC
SOCh
 O
PCl5HC-C-C2CH,N, HC--CHN,
O
CHCOOH
SOCl2 CFAR -CHCI,-Nl
GTRTCUNCR) HC-c-
CHN
CH CH,COOH AgO
H,O/A
NO2 i) SOCl2, ii)
COOH i) Ag,O, H,O, A
CHN NO2
CH,COOH
2-RCfRy-
THB-f t aeyer-Villiger oxidation): af-yf
(CHCOOOH

HC-C-CH3 CHCOOOH 1
CH,COOOHHC-
OCH
CHCOH
C-CH3 CHC
CHCla -0- -CH

U-T KISAL (Balz-Schiemann reaction): [HS

o9TATICATB kaR
A3T ATRUR (NaNO,) 9R
FKIKIAT Ua (HBF,) ARIT 0-5°C UAI K

NH2 N= NBF4
O NaNO,/HBF4
0-5°C N 1+N 1 +BF

C R R (Benzoin condensation): ca@ut I r

A 2
OH
TTIRT KCN> -Cc- O
A H
H
TTRRU (
 aT6f (Birch reduction):

(1,4-7RFICRATURR)
Na + NHa,

Li/O NH3 (1,4-aaatgRfera)

(FT1R1FR)
CH,OH
URI 1, 4- AA yoe 3 R
CST-AT fTR (Bouveault-Blanc reduction) ezR3, 5 MA RTT

O
R- H+2[H) Na R-CH,OH R C=0+2[H]. Na R
JFIPIR RHOOH
1-JTPR
2°-J11R
-OR'+ 4[H1 Na/yiat<PIRE R-CH,OH +R'OH

TEITT Ki (Cannizzaro reaction) [HS 03]

OTTSC 50% JTURR(U a-H
3A| IG A
7T As I A (disproportionation) 5R} T05R4

2H-C-H+NaOH(50%) CH OH+HCOONa
CHO
CHOH COONa
2 +NaOH(50%)

JiETtai AN (Intramolecular Cannizzaro

O reaction) 7RTiDT K
H-C H+NaOH (50%) OH CH,OH
H-CH-ONa THCI
COOH

esO faa-ajiETTAI AF (Crossed Cannizzaro

reaction) a
CHO
50% NaOH
CH,OH
+HCHO
O HCOONa
 (Carbylar reaction) [HS '01, 05] RPt
T I P A KOH RATI Teg

A
"H,CH,NH,+ CHClz+3KOH (alc)
CH CHN=C+3KCI +3H,o
NH2 N=C
A
CHCla +3KOH (alc)
+3KCI +3H,O

afzudRAA U , YNFRPA CPI *ETTT 6 1 ir

(Claisen condensation) T (CH ONa)-R ®fore a-H
O
o C2H ONa
O O
OC.Hs+H-CH2--oC,Hs-
HC--CH-¢-oCH,+CH{OH
RPyTBTTIACOT (EAA)
R-D at A R (Claisen-Schmidt reaction or Claisen reaction):

H
O-co+H-CH-CHO NaOH D-CH=CH-CHO +HO

H
O-cO+H-CHCOCH 3 NaOH O-CH=CHOcoCH+HO

NaOH
CH=CH-cOCHH, +O-CHO
O-CH=CH-COCH=CH-

RS7AAICODA
m HC-

Zn-Hg
Ca R 96, 01 03]
(Clemmen reduction):HS

+H,O
Zn-Hg/"11 H HC
CH,
CHCHO 4 [H], A
 Zn-Hg/115HCI CH2-CH3 + H20
HC
H,c--CH, 4|H), A

CH,CH3
ÇOCH3 Zn-Hg/ HCI
+ HO
4|H], A

faipAN UIITTIÍAR
A 3f at (Coupling reaction): [HS 99, '02]
a
ARTPCON JICA A1S1 Cof a
N - Ar IT
C S I NNA H Ar- N =

O N NCI + O-OH
0-5°C,
OH
(pH 9-10)
-
-NNOOH +HCI
p-yieyiCTitai

0-5°C, HH*
O-N=NCÍ -NH2(pH 4-5)N=N-NHO)
+
(pH 4-5)
UTTTSTtATAITAÍE
+ HCI
A, 40°C
N=NONH2
p-fAtATITITaT4 (7
14 D1 AP (Curtius reaction): TETRUT RieA A GIARAMR TE

O
e
A
R- N- N=N:
R-N=C=0+N2 11 R-NH+CO,1
www.ww

5 o (Dow process):a o 200 atm bti TCATAISAT M

NaOH 7R 350°C CU I T Afo CRPA UeE 3, UT HCI a

Cl OH
ONa
300°C, 200 atm HCI
O+NaOH Cu-4 (-NaCl)
AilUAT CTAG
 aPT (Esterification reaction): THS 01, '02] *4 HCI STM JRI
TT a

st1 O
HSOPa,
R OH+ HO-R R--OR' +H,O
1 HSOA,
HC-
0H+HOCH,CH
HCC-OCH,CH,+H,O
RiTT

3 - 9
(Fischer-Speier) PbTTRPC IF

fa (Etard reaction): TaR cCI, i CS,-C5 uTT PR aTRE 11 7

CHOC(OH)CL,,
CH CHO
CH3 OCr(OH)Cl,|
2CrOCl2 HO.
O CCl4

HS 2000, 02, 06, 10 fcUR B o r

I-PRD TAP (Friedel-Crafts reaction):

BFg, FeClg, SnCl, I CHM

alkylation): aisa A TCSTCATG
tP-FTFO UTTRIA (Fridel-Crafts

CH3
Te AlCla O+HCi
CHCI

CH,CH3
HBr
AT AICl3 (O
CHCH,Br
CH CP
CH
CH3
CH3 ATE AICly CH
+ CHCI o-TRTT( T ) p - 7 0 1 6( z T )

PIRIR
 )

A
 4
Z
=O +
O=U
 N°

N
4

GS

+
 680 reduction):
1
w e i n - P o n n d o r f - V e r l e y

TrURA-PTU-u fTA" (Meerwe

CH,CHOH)CH,
HC-CH2 OH
H,C-C-H
u ICH)CHOl,AI, A R rPTCPIRO (1°)

wfDefzRV OH
CH,CH(OH)CH3 H,C- H-CH

HC -CHa ISICII (2°)

ICH)CHO1,AI, A
RHT R
O

-=-
R116a f R - CHOH
S MN (Mendius reaction) J a f 1IATR FII-UT Na-Hg *JOTR

HC-C=N+4|H] Na-Hg/C2CHi;OH H,C-CH2-NH2

O-c=N+4 [H] Na-Hg/C,H5OH-CH,NH2

38 sCGAa (Oppenauer
TRU [(CH3),cO],Al a1 oxidation): [HS 04] 2°-C*K IT DRRA
OH
O OH
H,C-CH,-H-CH, ICH)COl3AI
CHCOCH, H,C-CH,--CH3
HC-CH, +
HCCH-CH
84 tao (Perkin reaction): aATCA Jaeut 180°C 7 A 44

TE TARO NT A i (cinnamic acid) H$ zTI

HCO O
HCH-C CHCOONa, 180°C HÇ= CH-
HC -H_O
O HiC- H/H0
HC=CH-COOH

CHCOOH+ (O
 a-JTITAIJ, UAtta1
aAT-0TA aa (Reimer-Tiemann reaction): HS o9 JFARAa NaOH

OH ONa Cl ONa
TRICIETR NaOH C H a 2NaOH
CHCl3 -NaCl, - H,O]
-2NaC1]
CHCH OH
OH ONa
CHO HCI CHO -HO
-NaCl O

OH ONa ONa OH ONa

CCl3 3NaOH C-OH -HO] COOH
O+CCl NaOHO OH
-3NaCI]
OH ONa
COOH HC1
COONa
-2NaC] O

o t a AIRIU5 kU
(Rosenmund reduction): HS 08]
36ZATrSAT5 fT

C-Cl+ H2 Pd-Baso
R R-CHO +HCI

O
Pd-BaSO4S HC-CHO + HCI
HC C-Cl+H2

CHO
COCI
Pd-BaSO4S O +HCI
+ H2 0T TRA
 URIT1ARTA Ru CuCl/HCl
NN A (Sandmever reaction):
CuBr/HBr CuCN/
CuCl/HC O-Cl+N, 1
ONNCI

NNCI CuBr/HBr
OBr+N, t
STATCTS

-NN CuCN/KCN O-CN+N, t +Cl

IRIATSA (Saponification): [HS 2000] 4 A SN NaOH a KOH-R e

CH COOC,H+NaOH CHCOONa (Ai DiATDT) +CH OH (R

CH-OCOR H,OH R,cOONa
CH-OCOR, +3NaOH CHOH+R,COONa
CH-OCOR CH,OH R,COONa

39 R (Schmidt reaction): H,SO, -S E TR 7

O
R-C-OH +N,H T HS A,
R-NH, +CO, 1 +N,

40 P RR (Stephen reduction): zRT C3aRER 7TT Da TE

SnCl+2HCI SnCl+2H
O H,C-C=N+2[H]+ HCI-22-27 HC-CH=NH HCI
IAIETET RERU HO
NHCI+HC-CH=
 NH HCI
C=N
HC=O
O) IH+HCI 22-27°C OJ
H.O O +NHCI

(Strecker synthesis) T-UPI NH,CI-4 sufoTE Afa

NH2
NaCN
NHC HC- H-C
C-HH.CT
HC-C-H =N H'/HO NH2
2-351TACATtaTTARIRa HC-CH-COOH
TTI (a-TAAI TE)
TRIS a-A

afet (Tischenko reaction): qR P

JUU (a-H 71 a-H I)

AlOCH5)3
.sAOg3, - H,O
2CH,CHO [CHCOOH +HOCH,CH]
H,C--OCH,CH
HC--OCH,CH
RTRTAT FEST (Williamson synthesis): J JRVCT faJTU

R X+ R'-ONa R-0-R'R) +NaX

H,C-1+H,C-CH,-ONa H,C-0-CH-CH3+ Nal

O-ONa +CH3I O-oCH,+Nal

f

-T4AT RT (Wolff-Kishner reduction): sqaeA a aRo T

KOH, 1 R
CH, +Nt
R-C H HN-N c=N-NH2160-200C H
LH 160-200°C
-H,O]

HN-NH2/KOH HC-CH3
CHCHO ATE1, 160-200°C
 HCc O
H,C
H,N-NH,/KOH
1 , 160-200°C
HC-CH2-CH3

HN-NH,/KOH
O-coCH3 aR5, 160-200°C
O-CHCH3
ACDTCPAR

451 S REt (Wurtz reaction):

R +2Na+X D
R 1 R- R+2NaX
wwwww

Br+ 2Na+Br-CH HC-CH3+2NaBr

H,C-CH,-I+2Na+ I-CH2-CH3 HC-CH2-CH2-CHg+2Nal

TCATURU

3CH,I+6Na 3CH,CH,I
+
CHCH +CHCHCH,CH3 CH,CH,CH + +6Nal

V - 0 fas t (Wurtz-Fittig reaction) JaR J R JRUT * TT

Br+2Na+ Br CHa (O-CH+ 2NaBr

aTCATCAG