Professional Documents
Culture Documents
(yenehun ilhManl)
Rene n)
(tkutkitio 7R-R
(Wuntz Roaoion) RX +Na
R-XPh-xN Ph
A
Radction) Ph-x +Na
(Filig
PhPh
Renetion) (Mamklamd Ran otioen
(Wmann
Ph-X
Cu Ph-Ph Ph-X n Ph-Ph
R-X 2n R-R
EHL RadialCaxbamien both a intexmned ate
Um 8X
ROs imuo)ve C-X Bond AkU
Ca
Teduco
R0-R 8 RI RB? RCR
Hoignad favmatien
R-X 8 R-Mg-x
MgR M R-MgX d
2e
#(Kolbe'sElecbolaib)
NaOH + Ho T
Cuhods-OH R-R
F
* CO
* pH
Tn casa
RCOOR
&
ma
l
Radical Tntevmadiato Fomad
H2 olhasts at omode
dcum
o yaxmie
be
um 00ases
majon R
aid (Hcoo),Ha
anmd
(NaOH
us
11)
cathode vospeotwely
terthay .
amdl cathod: borth
02 HYDROCARBON(02)
t#
(Photahalogemaben
Uabe
ilpAR Odical untewm dinto obtaumad
:ds
TniliatenX-X
R-H+X
hN2xO
XKimelio dsotbpia
Kumelio sobp'
raumation
aotu ohsued
Hc-0C-T)
fee" Hadical s Ros
RO +H-X
R+X-X R-x 4X fatan Oadto slabilidy
o ()
2
Rates Rados
eidias unto T2 by Reachivty Reactio4
o:A-(HLO3,HNOs) (1:
3-8:4-5) 80: 1600)
12 3 3
+HRenction oithNBS:-)
(ECeobophllin
dddilionReaohion
A
N
x
unmaroel
have
X Camt y
Y
*closaical
y
can'haue
unshaod
Non-caujcal
Caxbocotion
cc)
CC Carbo caten
(NCC)
P2
Raagent e Nu Path
H-C4/H-8M/H-I
0- Co 1
H/H20
di
eH Hso @
H2SOy H HOH
ROH/HO HO ROH
RCOOH H HO RcooH
X2/CCy X 2
BH2/H20 aH HOBy & Ha O Br 2
Br2/H20 un Brime
boln He 0,B9 ca 2
NoR NO 2
TN3 2
CH2 ECH
1)CH2 CH3CH2 Canbocauen yamod /abtauned as Pntbumocua
Caxbo cationstabillhy
4tabilihyof alkema
HYOROCAR BONO)
CHaCHXXONdu
) CHa CHa CHa CHa
Cc
du ala
XNon-cdasaical Caubocahon (Ncc) nteuma
Gxd
XNo- J avoramy em.om.t
2) CHa-H2
CHa-CH2 XInvoloesamti addibon
R0:R FaCla A1,2
tà
TptsAkant
(-munms
dnti
()ym
P Procduct
(-)
cnt
(4tis ( (+)
(4)
X
#(4Um Poc)* Uatd to elaet ums wm compo wnd
aturatien,
XReddiuh Bxown colowt o! &2 becomes colowloss
+X2
&oon
Coloun O (Colousles)
O
#RCPand TP RcP)
contalled
XKumatically *Theemo dy namicall Conty ollod
Rat (fdst) (PModue atable).
Atability
fauourS at dow dmp fauowts at hoh domp
* aloays ,2produet s amumed Ttcam he L,2 0 14
08 RCP
JA (maould
Poor
highayumstablo
(Tum@)
CH3-C CH,
dus do (+Ue) On alken
#Kuchvou Randen
OH
CHg-CCH 17.HgSoy
dio Hasoy yold as vy g0oa
Tmum@)
(majo)
OH
CH-C CH
H20 CH3-= CHa
un amd amti
both
0o Hadue a
R-CHcH, oC NaBHy
NaOH
R-H-CH3
(*Hg (ofic)2/h0 OM
*NaBHy NaOH DM
06) HYDROCARBON (06)
R-CH-CHo
B2
TC
THF
H6
H
R-CH2CH2-BH2
R R-CH2-CH2 -B-CH-CHa
CH2
-
R
BH3
CH 2
BB
R-CH
BF 8e8F
HBH2
h4MCTS
CH2
A
*qn add"
|2)(R-CHa-CHz-B9
0R-CHa-CHz OH
OH
X2
NH2
R-cH2 -CHa-X
R-Cta-CHh -NHa
7eidation) H202-H20
Hoo
RO
RaBH-0-0Ra-B86H 6-OR BOR)3 B-OH
Rovo RO
6
3ROH H
A R
OH
B03
3 RO
B03
XRx
Commex.ciad mažhod
de oxm phanal
o-0-H
CuuTemLR HyduopeH0zidd)
o-DH
H
o-OH2 Ph
pn
Bieh Roduction
R-CECSR R---R
H
2)
c-C
RCC~R EtoH
RcC
H R
RccR
h
COso T- Na ig,
NHs
EDH
e
EtOH
Caialhie Hudrogematen
HO daion ta tA 4 us am
enample o additien
A) Atum CatalyatQumaluns
* Tn cae of conyugatod
duu
dibna
to 6MCTS
L,4-
takes placo
addihon
yoROcARRoN-(o0)
F(Rasemmumd
Renetien
R--Ce H2 R-CHO
Pd fwdhuot o dalt@n H20
0H
BaSOy
pau oxicdizehoga
R-CHO Ha2 RCOO
RHt (Ha0 /Ha02)
*Ozonolyis Zn.,s
Og3
R-CH CH-RT R-CH0 +R-CHO (duotwe
)znH20 020lysis
902ygan trapp0
i) Og R-Co0H +R'C0OH 0zidabwe
i)Hao H202
o2onobyai
Og
H3C-CHO CHO-CH2 -CHO HCHO
2n/H20
03
Ho0 lHa. 3C00H + COOH-CH2 -CooH + OH-C-OH
202
H2 C03
CH3
H
H
O OH
-OH +Mn02
Mn eslo
indevmedido
o CH3 Ayn
qyco
Add
ubatien
HYDROCAR BON(O9)
CH3
Lochemuby-
-0H
CH3
KMnOy
L7- KMn04
CH3
Colcd
OsOy H0HOH
H
CH3
CO2
#PHoet kekulae8-
3x+ 24 + dimelhyl
Z
CHO
+CHO CHO
CHO
O Gyoxol)
CHO
O CHO
(mathu
yoxal gyoxal) Dimathy
faimehy
HOxal
HYDROCARBON(10).
7T Complor
Colbr charye
(Elacbuophilie
Rxn
Mechamusm
J M
a H
*o Comploz
*Cavbocahon
,
Ke fndexmoclicb
[O) *whe dand
Comp lor
(1weAible) Reuveraiblo)
Eve
PE tabd TTodinalion)
utnh
Biomolecula (Alklaion)
Hale =KA-H][er) coCboylahen)
(soa,
gadeous produet
Sulphonaien)
D
P&
PoR Compx
A
#(Reacbuit PoR
Robinhood
EDO
o] Rat
(+R,+1)(+H
(aclijvang)
3
(Daachoatung)
(Net-7)
2)
lo] Rada (CR Robinhood eWG
(-R,-)
(D2actuai)
HycbvocaNben(1)
tntahisn)
& DO &DO EDO
ED4
PoM)
2
Mo
Robim hood Rcbinhoed Aobinhood
Robinhood
o,P>M
PoM
Robunhood shoos Induehve
ect(-7) a achi
Resonanca
ct (+R) or auentahen
actoxs Forauentatisn
ei\k
1) B AtablitO-Comploe, dacido the maja pioduct
2) bame
3) AL
-Comp en ,Hhem
yactars sama Hhon
Aluia hindotwm
e uich it
D T (P,9,9 elaebonie ecto alk
2) sizeo} x
X 8 0i(9,5)
3)texicefAlky
aO A
OA
TO Monol 9)
P:9,s()
o-N
HNO3 Ha SOy
OH2
Nog(hHao
HYDROCARBON
O
2
2iso
HSOy
No
. (12)
eordboomdo
exnmplksAS)
HNOS HS0y
(o) NLLbyatLOn
Conc Haso
o Audphonati @n
R-xFACl3 Ak ahen o
Nehen cam b)HNO3/ H230y
Nitsaien Aenolin W2Os CHcooNO2
No2
oYtoM 02 Cone HNOg S)NO28 Fy NOgwOy
Hso No, 20
2) B Cone HNO3
3)Py di HDO3
2H NOg H o-NO2 +Nog NOg
+No2
NO 2
( NO2
A A
4)8oyBfy OA oX
ND,CIOy Noy.co
NO2 Bfy
Nfo
ND3
0 C00
CH3 O1
6)B HN02 & HNO3 No NO2+HCA HtNal Ho-ND NO
NO N0 HN03
(o-A-)
HYDRocARBONJ (13
ubatienAnilin)
NH2
NH2 NH2 NH N02
HNO3/H2 S0y
NO2
NO2
(27)
(47 7
Roasen DO de aum alion (S7)
Mcy@
Mayo
Ac20/Pgicin(trong
Aciclia
M A Maclu
8Ac0/Ppicio utd
Fo lBrthyYeld
a
WHAc NH
NH2 NHAC
Ac20 HNO3 H3o *qpod yeld
PPyidune HoSo4 O
a HaSo04 NO2
N02
R-OH Ac,0y
Pyicine R-CoNH2
hl Acg0
Pyidine
OH
OH Pioxie Acuol
Cone HN0 NO2
3 Bad Yeld/Pao7 Jield
OH
Conc
ND
Ha SOyNO
rNO
O
OH
SagH
SOgH
N02
Cenc
HNO3
ON O
OH
NQ2
NO2*PucrLe Aad
Good iedd
HYDROCEARBON(4)2
F(Cbulphonatien
Readien KX-may Cond H,S0
SagH
Ranction:[0)
Mechanism SOgH
Conc:H2 S0y
HaS201
H2SOy
t HaSoy
Xmay
OH
Ha9/
1)X(un
afW
Os
Mach.6
1)xfx
a
FeXs8 Fe xtx
x I2 eyeribl
So HNO O H
LO
X-X Fe Xa
O2 /ho OtAT
(encos)
[o Ceacosb) A
HYD ROCARBON (IS)
Halogen atien on Phanol
NPS
9
OH
Rta1(CSy
H Anio
CC
CH03
QH
XDuy ts Haum atitn
BH2/H20 B
PPS
B (1ohitoppt)
Ph-o9
+ (Haloganalien o Anline
0H
BH2/ CS2 By
NH2
CCly
BH
OH
B2/Ha0 B
A)MAAA
o
X OH
SogH
B HB/H20, Au.
HUeHsyble.
B
(ALrylatisn
Xmayba-)R-x lLeis
Auid (Fe,
fex3,8F3,
ARX3)
2) R-0H HO
3)ADkume /H
) R-OH 1 Alkama/LA (BF3)
Mechamism-
R-x-AX3
2)R-oHH R-OH2 R+H20
HYORoCARBON (16
3 R-CH CH2 H
R-
Cawbo calien us obtaunsd as untewmocliaty
R-x
AL X3
ALK3
2)(AcRatien)
K-may bs3-1) R-x/-
A (AY3)
( O
Reac-[O) O 2)R-C-oH/H2Soy
R-
3 (Rt),0/Ald
Ha POy
R--0--R R R-C-o
o-H
H R-C~oH
R-C-oH OLACR3
oAL CO3
DH
u)
ACl
Vey (
impov tant Maund()) Aclu (2011-2022)
IYDROCARBONI7)
u Catien us oblaunod as imtewmadiate
RiarHamgemand not
possyblo .
Hh achuatod
H
ung doesnt how hu utdachon.
OR--x
Sneess amourt of L nouyenr
*Aylalen sbexod ouey alkylatiem.
favmyl atien
not pbl
H COCR ALCl3,cotHU +AR3
* Gatomam Koch ReaciLPn
CHO
CoHCO
a
ANcl3
O CuCR
do neutnali tha HC
If
*Ppurcling
In
, RH
addod
than
aceipadien
wa0
wn, mass
ze
inouasos
)
is avmylalien.R4H3 than
b42 gm (-C-CH3
"Acadabion
#F (HUnsb04 Test lA M
Ph- SOgC a9-KOH
RNH2 Pyridsre
NH-S R-
AlKal
(Hünabexg )
Raagert) Aulphonami da)
Ro-NH Ph-S02 Ce
R:N-
PsidinnRzN-o2koH
Alkal
X
Ph-So20
R3-N Pygdimo
HYDROCARBO
t Poc) h
N19)
li
*acd to pate and dotiyuih 233 amun
A
Ph$o
(3
Amine) fithey (1Amino)
add
Cits
2
00.
Fomt eot Reactions
O D
OH OH NH
Zn
+Zno K2Ct201
dut,
A
(8em20quunêna)
# (Diptiatien)
Rxn-KNH2
Na N02
HCA
R-OH G 0 on
Machanum 1 Na NO2 + HC
( Ho N0 HNO2
oda
(Nitto
us Aid)
NO
2) R-NH2 R-NH- N=O R-N=N-OH
3) R-NFN-OH + HU RHM=N R-NEN
R-NNf0h2
H20
4)R4NEN
4
R-OH + N2
OH
(Maya)
R-CL (R2NA
RaNA faN-N 0
Gydlo aillydog)
RNO2R-
H20R-0H
+R-0-N0 NO2
XCanbocabon umteuma
* Reavv1angemont may bo pasaiblo
diate
os
Ph-F H8Fy Ce HCO
Ph
H20 ay
Ph-0H CuB/H8
Bei led Ha0 PhB O
Ph-NO2
HBFy
Na NO2 /u CuCN /RCA Ph-CN
Cu/HCA
oluble Ph-o
HsPOg +0 W
Colbuloss
atoy
CtgCHO RIPh-Ti
HBFy PhN2
R-NO2
H2/ Po
EthoH
R-NH2 R-NO02 HCA R-NH2
H2 F2 R-NH-0H HeRNH2
R-NO R-N-
*3mo H2 H2
AA R-NH foH2
H
d -
R-c H
H
Sn-2e HO Sn -2
R-CH =CHSn
XH
R-CH-NH2
-CH-NH2 4
R-CH2-NH2 Lud =6
FSom otheRenolens8
V20s
2s0
O vz09
Soo'C
(Maluie Anhyubido
ol
CHO
CHOgCla
HIOCNOHC)
U 2
2H20 ,o *&tand Raantion
CHS
N
CH(o GrCH3) GHO
CHO3 Oolio
Ac20 2H0 0 NH2
NO2
3 Sn HC
NO2 R
H HCA
NH2
6 HC&
NO2 NH3 HS NH2Aadecotu
L-aN7 Redn
(MHA)S Wo
(Coupln Reactien)
QH OH
ph ca
*C-NCouplung
Otamge
Sight Bae Colod Py
*Antibiotic
NFN-Ph
Sumnay
NH2
NH-NN-Ph
Ph u co9
o N-N Couplun ht Bas Phonol
aightBass
(Paxa)
NH2
NH2 6lightAide )Anilinp
Phn coG C-N Counlung (Pana)
Vedlo D
) NN-Ph
Nothung Momhon
N
Aniun
N-N-Ph
0H PhN OH
C-N Couplung-
O daut[OTo XRod-ColowtDy
H PhNa OH
n*C-N Coupling AU
Atight Base [olo
A N -Ph
HYDROCARBON (21)
Chemuty
k)Ractivity
f
O
Naphtalene)
6R S
* Foullbmoll
Rxn + 3H20
R-NH2 CHU3/KOH R-NC t3KC Only by L-NH2
O
Machamum- )R-NHa)+ -TH
- ca-0H
R-NH-G
a R-=C-
R-NH2
0D6 U
-H20
(
DR-NH ol Auno72l M lil il
c) R-Nfce R-N=C
QLchlayo axbene u Obtaumsd as un teumodiaty
Move e densihy on Nmwo leasily
Vattack idm oi
*endy shown b Pümay Amunp.(1°)
*L mol CHC 3 3 molés of KOH dtequuiy ed
OH OH
CHO
i)CHCR3/Na0H
i)HO 4O (Minan)
(Majo) CHO
oNa
CHO3/NgOH Intewmadialo
o LD/ ROS
CHd2
Aubstitalod
Bemzal Chloide
ONa oNa
2) CHCR2 C20
C LonieChalatien
OJ
HYOROCARBON/22)
Di-chlavocwbene us obtaumad as intexmadyato. JUNSAA4
*ctho s maj@y pHoduot duw to ionic chelato
Anothor intewmediato s substitusd Bunaal Chwaxids
* allpasilionsax blockad then attaok yrom Pona
# (KolbeReaotisn)
OH
OH
CO0H add
*Salicylie
NaOH
+Co2
H
O
O
a
Basie mduum s gwen umow as of bemzen
nueleophilicily
bacauss CO2
wenk alacbi
ophil
tho dubstiiutbd s ma@ pHooluct bicusa uo nie chalahen.
We com also ust (CCA)unstead oCO2
(Ouidation with Hot RMnOy)
ut ww e od
has amyH O RHOs enthom Conu
Bemzylic Canben
Ban2ofc acid.
C00H \OA
CH3
RMnOy,kDH /A
fo CH3 Hot KMnDy
CooH
CODH
CH2CH3 1
2) oCH3 oCH3
HYDRO CAR BON (23)
Roactien
HAH
(Phcoa)
2 Ph +H8
Popepation)K
(n Hadical.
9 8B H-B ,B &y
Enample o
Anamaxkovnikou
u s
Radieal adelitionseaotion
addibien unvolued.
N8S 3
substitubs only allylie Benzylic
pasition Av 3Ph-c<
* Puwra NBS us Jmat bo HB Bx2 s added as
impuuty
B
NBS
a-S(T-S)
t2) b= 9(Steuo)
h)
(c 8(cc)
Bbt h B (9
d 5(Frachon)
B
(13)
POmahon
ytydbocakbon)
0)HydbvolyuoCobidas
*AR Ca+ H20 4A(oH)2+3Hi2 (CHu)
6) Aomatiuation
|O+ 2H2 w l
2H2
N H2
*O 2H2
(o CH3
LCHs
CH CH o
CH3
) CH3
CH3
C)Tsomeahon
Alcls
H,
8-
(mao
HC o CH3
may@
(maqa)
(fenchons tydhoCarbons)
a)Combution
CxHy+)o2 xCOg +H 0
b) B KMnOy, D (only toith 3-H)
KMnO4 OH(Teiox Budanol)
C)Nbraion
NO2
NO2 + CH3 NO2 + &tNO 2
HNO3
A
d)AudphonizuDnR
SOgH (
Ha$04 + SegH
e) Thcomp.latoCombustion
3) HCECH Cu22
Nh4C
Contby@Wacd xidation
Cu CH304 (Mthanol)
1) CHy+02
(s23 K)
0H CH2=0
2) CHy +02 MOg03
MO203 CHL
CH2~0H (Aldehyde)
0H
MoCHsc092, cH-OH CHaCoOH(thamoic acid)
3)CH-CH3+O2 OH
CH3
steam
hReaction toth
) Pprolysis(Oxaeking)
13
CyH3
6Hi2 + H2
+C2H6
CH4 C3H +CaHyt CHy