**

CARBENESE
24, , 202

NTERMEDIATES:
REACTIvE
diunlhnt deribaléus
7hese ane neutad nenbnled
O Caráuns
Cntain a pair
7 Carba
vletrms
.Ph :C
:C H
H
C
R,
C -Ph
Carsene/metylenu duatheyk diohlbro dipheryl = /w-140
Cahara Caráen
Ckróem

n sexlet Alape
0Cardn is
carhom i a ebetron claf'i enp
arbens enpectidhigay reoku
o as
lckrophilie in panerad
an o Aghes :

aru
o hmded lchms
o senut arsen Non

<Vac. p-orkdes a s rkird

eng danajnelte

-C en
nbonoded
AKan olue lo repulsia
l2o
leron aik 6ndrd
lutiu
elckons A simfla Carhini :Ch H--H
10L CAn n 120 Yyurad
spkybidard 'curdn = nem
LM 2.5+1 M hlhfAaa,, S alpeó'e
Apis ehckm
wWhan Apan a +1
hanld s + M= 2%1t1 =3
CTrat). 7= 2xot//
Stii0,
ara ad aani/ba'rd elerns et).

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 4haa sh a painf
7hus oAißzreliy n nsairad (hanalej
(ak'paraltul) a Callad
prsel
y v aAAA
Cardenas a

lendd lack a
Triplt carkene
p-erhilas,
paramasrili'
f=f Aan a mafnél'e ma MA an
(F
ha shrdiad d esr/epr 4petrney)
key
baidiand nnd fr C-R nd)
tn iebmn nunidir
Z-c-R
125-140
cayáene t 137
7 -c-t fr senplu
Trpet carsend lipktay
e sasle Kan sit
CaYbm apbro
P12-140

hcoplo hleiaey ht h-c-

Sen 120
Tw
1fo (as vaphiPed
ky budiad Cardn ) bat muh cloa t
S hybniediod tarda)
(a hird ay
Al
i

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 Whare us eln rinain
evitd

GEN£ RATI O. diago

kockanies
1) Soposih'en ymad/Ao
Conano (Rc)
R-C hv R

Carken e
L d
E
ckev On oa
Carb
/fosiod, fdtazèrine
tbeihion 2K
(
R2c= *I- CE0:
co h r
K D

R
(+) AR R

EpOride
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 N

( R
denlaA
iazin sry
, elninni'm 4 habels dy br

CH
-:ced2
-Ht
gam
2 Ch- sed
ay MaLi )
CH MA :CHA
H)
Av cH,K n-Aa Ar Ct
-Hed)
. emboih'n
ae
d Na dr k- Aat ihaloaciue

c CO

Na ec
9 FATE Srcu md Yeacho
Reachos arbines
fwn qeleprobae
i) Adlih a to ce Cc (
lobropon dinnafu )
R-cH=cso
Rcarra R-¢-44N, R--Ch

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ii o oerh'n akvn

C
CH

CH -0H 7Ch-S-0-CH*
ChN
oiv)
K2 C
R
2

Adl Kn
Carhn d endergoes ydoaddihm n'k c=e
m ulorobanu deri atiu

CHBY+ be-ok

cA jenerald

CucN
+ N CH CoDA

CH Zn- on
Sonieaa ole cerbenoit
speis
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 7r DDTON 7AY
THE NATURE OF_ CA5ENE
OA
PErEDING NON STERE OSPECIFIC
8E S7TEREOSPC cIFIC oR

sngket carker cherg Alrevapeufe aoduu h'ay

t ce)
num Aureodpecih'< adih
lA Cardena unolergo
Tnip
Ainglet cerdenn aLk in
tel odh'an
Lniertol
Areospaefte tau'rad tn
ay, tt althene
7 STereodens taprpana
ro duet
R +
R (aiyl) cis
(rans)
I

(cin)
(ig) mus
ly
7hus ndut skreo he
alkyk/aryk e) depends alkune 's sliwdn
(R

CH

No
ya an Kenk a an hchphile a

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 -Vac, 6-oritr{
"H
Fiu d spdilef

Additio a iklt carben an alkenà

Tuv nee 6ip pra (uolue a olraotia

)
nTirme oliat

m sreospeufs'r
KA
H
H

TY C

C y
ra Carhen
Ccrben
L Co-rben adolsacros a cc fom yctbrypenu
oled uaau.
ae nz kens
6tresnpausfhenly cn
Ce 94neratid ram dazomihnu
)

4d em 2-6ulana

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 Skeul , al n 75 ) Hs) tuw
Arnet et. al shaeol at Alirunpeih7 addh'
kMostt han KCaicd oat rUna ¢ nkartE
coa mixi e and m yloprabaa
odoiuntiua
Huttyle Aurunhun gcnwnahd y
adds n nnsaresapeah manner(G
Ker po ouend carbtne in Kihbt )

oliraclicl nerma eiai

Cnasid H

a aimikar ay rann Lken uik sioyah

Carbn iu ra rdus
Bohiypanilk
dechon o panalI ohar
nety nd potsle

H (A
Carsn
ornolieM Akrme diak (A

ah'am
VV m
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 Nad sondiiy

knbeyniar
Sp
H 6 ba linen R
(A) k Na)
(hefr p-c 6md
bfr
rh'n H H

K
in (6)
Mhm mbunin
Nby
NAs
N

( (

C-cJm
Frmaha

S 6 e) &

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 -
mas alkema Yeadn tn ereogkcc
Culaxly

i ribt tarbne
carlne
Ch Liut
H
/R
Many allem T.S
(Mo
Tmediali
Prs Cmsiny Cocerkd
i formad)
goh

cava
FLt nty dat
Ch
P N

Sp
yomy
aLkm
(D) C
bd dradie
neemedeA

(ETt
.

Spm mkerph

C
nd F)
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CARBENO1D
carsenus alhay
ane uapenk Kat áekatue Aike
Thae

beung u 7kem ane a mas kud Caráen (

CH n9

O S1MoNS SMITH REACTION

Named afar Howard Eney Sinonn J, adEhald

D. Snip An alns
2nCa) 4cu aycoprparn sliah'u
CH7+Z (u)-

Mckais!

Zn-9
y. Y.
. ZJ

Smierh'

HO Ch
CooH

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 **

2n Ccu) /Ek
RM)
Cca) Ac-
Ch 2n
Re EtA

de cH, rakuly Cosl

Kase Auun mad meluot"y

YLasho
Ypla t AY
by
Br Am tontl, )
omelhont dertuhus R/hr
eun y
ota3 ked n( t
ha E a-d Ch9,
uruKaDU modif'nka)
FURukANA MODIFICATIO

a modfAuh n Simns Smi ashn ahu

n hud nrali Cardenn d
E td C9,
ue roud yiAA,

Zn E 78
P CMF9
ph
Cann 20oBn

O F

,J DMESuuma
+
CA)
Bn
S1
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Proolust A) mzn an

CHARETTE MOD1 F) CATidN

vt s
Heu Zn9, ad diago mižKans dnihah
produu 7lav henwnl tnkermaole'aá ,

nT + PÅ CH=*2 P
Phtnyl clea3 onakA
9

Bkayn a nh
Scmun Srnid rard'a Alue efect

CH2-2-9
(R A K))

-OH emlsxed
Cenbrll pnida ataa
Somu furer narpl
E
(1) o Co OML CooMM
DIB

Mc0
OBn

3
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 (r) aeahk
(i)e o Rh

C
Mo CooHu

RO

A CoM

shebiliz Caráne ae
Carbn 7y
A
Cabinaod aheeiu

oi) Eh
C9

hultini Hooc
C&DE
Nh
HOOC
cilas TiAr a B-kemane

Caac)
in)
N Tout
h

CHCrdE CoOEt
tcbaplik
CaYbAm h

,2-
CoOEt 83 7

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 IS-
haush u teoley
ra-onL

-CH 4+
SLneri CK- -4 Rclend slabiht,
sheo taf
fatr unprolis
rooluc lompoaik'7
o hAcrhon avluwn a ALe O-H_ d
-
R -
-oH+ Ph2cN R-C- 0-Ch

MuckaM

NEN Pho +

Ph-0-ch N
Nik diret casbenn rccha Cam a
prnenled a CH PA,
R- h+Ph R- CH
RCoocH 2
*******

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 - 16
a mure Aubohtuli
Caysen alinyo refes 6_attacR
drrsh bnd
CH

27 7 67/

Cupalid dienn fe
an
, - aldA'a
6refesd aur ,4 adodah

+:CBY2
887 27

NSERTION REACTION

t C +-Ch-4 t

CH-C4 C Ck-Ch-
C-H C

ma

h
-C-),
g 25
C4-CA4CA), + -4)-%
24. 387
6
A) -, 13
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 7

Hene cKerA as nsfrmued

Carben
R-oH + Ch r :
CHN C R -o a
R-oH +

acddily alshtè froln

CH-N2

R-9H+B
REN R--
hiy id c
Alcokok

82 Ex6loin
dieg omkians
REARRANGE MEN OF ARBENES
car6 Cnus.
ey Mm f keto
9ts T7

to frm ktins WoAf

R-CH=ol
CH E Keline
Rearanak

Avn oltE%Yt aadm

Cmioder

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 -8
R-gd &razokotöne
TRe ic3o ktone lermeelinte whu's
foYm klne i prurlenet- -esler (Ef Aier aleh
ta fm A Anal
( az n acd
ed a onlet)ahid
a t ua ny

R--CH-N,

kearay*nf
R-CH=C=d RCHCh
Cavben NH,O
MaoH
R -cONh
R-CH Coo M

R-C : R-Cy c R-cu O M

Me
M

R Ch

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 -19- OF CARBENES
OF CA RSEN Es /NATURE
AND REACTVITY
/LITY mone
carbenu m ligktly sask
ThipLt
sirglet Carbene
mubtibke

9ialkyl tavbeu gronol slt rket,

R
Eluchm donatirg gra-sa CEDG) a

am
pair 4K esk9 6-ordiTd

O
: D
X= F, d, kr e
OR NR e

siyut Carbas

eiyht Carber

dlocel2ahen

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 wwwww

-20

LnMt Carstnu
o Taslht Corbinus
Sfal avaumA skI)
roemd
:CH CCA2
Pkè CH
R-Ch
Ph ote c (one),
CNR2

(NHE)

a)3harl carbaru it carktrs y?

tnfrun ne,
A at aht a

-rbad
haa pair ekram ' ia
akaki lize

:c

Carám Cardn
elchon olufruona
Comhtnsnli pmly
dipknd
ane nU m am
arben
plaa
wkeny r
28
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 .
21-
PA P

7Ke cerhena
-oifKauy
(ecd
Can uu mlo ef ronana

PA

-PA

Ex Aenaiu )
< Cogakin
Sfakidize ,
C)o Caybohiloxy Cardn a phe Carsenu-aA

ROC R0-ce
uaceanF
2
- kid arhou ars a
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 2-
OE CARAENE
O REACTIvTY GF
CARBEN Et /arURE
attrKud t iE
serp arknes
van ous
salebti-rli
Chevactirzad a taskekta- Carden, i-%Lbie
n
Carbnes dsmdu
Caydene and am6hele
ubnhfusk (su lules
Swryat car bene ( R )

Flerpile Andifkie
o Nchopel'e

RO.
: Ro/1e

cooEE
CA tR
I-9/-R f4
ckA
ata atcdd
Carbine Caréon
Cenke 7hus
Sueh Y onch olehrint
amayhke
Caysn rdah'ul nalun
ean reth

nlkox, Carbma do aeld alhunn

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 23 .
9maliox Cr 6tns t a nucAwkheLe caYhne

Me MLO
Meo

Meo Me M

Reo oAanei dacnnas,

dckm deftulen

adeh'an Cc
CCou), deuy eak

Ph,e: n ranthin ai ) Meoh gis t424o

i MeoH / Naw3 u Ph c# N
MuOH prohe solurf acty a apron odnan
M-o
PA, Ph A
PhcH-oM

Ph, cu
i9 (A) Phac CA
TA Lnehald t (ha hu

a mlophi'k'e aerden aces

7wn Cardoehen n aatkis
Miw Mo
23
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 -24
Sma Prablem.

CAL '

oo
(a) L Co OMA

+ CHT 13uok
Ph Ph

+ M h

7u do rmene 6» dud
(d) Pho CH

.
03
Wu

ait
doam

dnn
maonanas

w dut
daráyAemin

voluk frmud
arnd

+ ehch t KoH
CH
Koh

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 -S
cH A B
R2c=cR
and 8. Explain A 7ovman
IdandibA

Erplnin

CooH
6
Exlain d
N Maoh rmgh n
7. PKoTolytes d tasA d olia3oaialelhydel
A) Huoh aols multl acutnk titE
6randhiy lahehy
H- CHN Mo C ofe
(A)

Expi K muans

/+uek t kay )/

0 . hhat ai a l nalare rhin

Ph
P

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 - 26-
Sp
A a inptt Carbinn

streeapeuhe So gr'uen anh r h4

trya Cm crcd Vaha CedM

+L.. CUrvtu

Co o Mu

(6) CHr Bok :CBr

C-H

Ph CemcrkA
a yht crban

I a rikt carben 24 actelo a

/
2-bwlan
a x hboeduck
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 -27-

K
M
M M
(ca)
(do Pho CH

(Ende)tin) Exo (
n-uli Na-
n p)
-L Meo - (Lpht arber

Meo- c; M
M
Cenured
a-eloluh'a
Mcs)

OH

tCHcl t ko TiemaA

CLAam iy jounelf

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 OR
t Ch Fkoh

C
(l ast4
ccd (iyhk tard
rdano
2 ale o elcehoka'he
OH

-tT
CH

+H

Cho

iilery

ccl CHcl
C7F Can nd aro mahaa

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 hy etrohyae4
to aldhy du

CH CHd eopertyl Aatca

:c (Lyat, hkrhlils
Cahenn)

gchr
R
zc=c
allen
durihi
Abo am hu wi lun

+M
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o Cuch ec
CSnt,
ELchrykil Carbir

Cbann cnlyard
luninah it

Chun

Tarra m

y Cnpac4
-Ko Carbtr

-Coote

e +H

COo Me

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 a .p siylt carsen
9t
I
H-C4 *

2
H

I
Thern rbint I and Z
eg ibr diem ta m Bgoi and
Aa bedtA ha alrsndy des bkukA

- Kito arsi
O=-4= C-ot
OMe
4) 12.
o Tahe Cah rzarrary a 4fr
MeD

oM

E--on (8) 7
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 32
ro etueh Can rm tik Acranbler
akattd Carsn

:
/ - /
ipat Caybenn

necanf
(aromah ckaYaher
ape gdeprhan r)

Carbyamnn at a lt
preranz mA (armahe
o aiI ). Men a rmay ameha
henbef i CAd a arite kay
furm a hroxi'cusAmalU elue
prhah n uky /cA s0yand el
hoio ) RNe r rwe)
T ea ch'n Amuobu

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 -33
hoR ( leetrophile 'a, senpit
CHd3
EH
cd Cardtn)
-HT
R-NH
ko

HA)
oH
-N c
R-N= CH:
CalkyA dyancd)
R-Nc

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