CHEMICAL AEACTIONS : 2efer,

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NVCLEO PHILIC
AbÞITION
Q: Why do Aldehyder and ketones undego
nuc le ophilic addition 2eacton 7
Ans Bo th Aldehydes and ketores ha
Ketones have polar >C=0 bord
Nucleophile atach electophilic dive
Carbon the
pola oup fom a ction perpendiculas
to the plane sp* hybmdised ovbilal
can bonyl casbon
The hy boj di sa ton corbon changer form sp'
to and a tetqhedal alkoxide intemediate
is poduced
This intermediate caphore a pofon fom the eacton
mediom to qive electicaly heutal poduct
MECHANNSM
Nu
CH3 slou
step-1. CHs H
planor (o) Tetyaheda) addi
alkoxide odvt
intemediate

Addi tion 2eaction

Trapontant Nucleophilic
Additien of HCN fovms cyanohydain
H

C0 + H CN
CN

Methanal
Methanal cyonohydin

Ht CN

Elhon al ethanal cyarohydn

 Convert Ehanal To Lacic Ad
(2- Hydoxypopanoic 4ud)
OH
CHz
Ht CN CH
ethanal

CHQ
C coo4
CN

(2- yoooxypopanoicaud)

Additon of sodibm bydogen sulphite ( NaHSO2 )

CHR
C=0 + Na HSO
oNa

poton
tvansfex
0So, Na

Ethanal bl sulphite addihon

poduct

(
NatHs02
Na
CH3
propanone poton
rersfer
CH osoze

OH

propanone bistuehite
add1 tion product
 Aavantaqe of this metod
NOte The hydoogen sulpbike add itron com pound is
back
wal eu soluble ond Can be convested
oiginal cos bony compovnd hy tveabng
wilh mineral acid
pusficotion
Therefore ueeful for ceperation ond
qe aldehyde ond ke
Addition of Alcohol:

O
R (OH

OR
doy
Hl
Hemiacetal Acetal.
Aldehyde
Aldehydes eact with alcohol in presence of
jntermediate
alcohol
Hce to
qive alkoxy further veacts o)th
known as hemiacetal whjch acetal .
One mole cule o alcohol to form

CH-oH oCH2
R
C=0 CH, - QH) R 0-cH)
CHhylene Eihylene gycol
ketone
ketal
Cdihydnc
qlcohol

and ibs Desivai ves:

Addition Ammonja

NH NH2Z
desiyaive of ammoni@

H+
C= NZ
c -0f NHZ
- GG Hs NHetc.
 (a) Addition of Hydoxy amine ( NH, OH)formr
OXIe
NHoH
Ethanal oxime
(A cetaldoxime)

C OH
CH3 CH3
P>opanone oxine
(Acetoxime)

(b) Addition of hyda zine NH, NH) ’ fosms hydazon

CH Ht
H
NH, NH2
Ehanal ethanal hydsazone
CHS
NHNH2 C
CH2
propanone Propanone hydrazone
Addiborn
of phenylhydrazine ’
forms phenylhydsaze

NHNH6H5 C=

Ethanal ph nyj hydtn

H,
CH3 phenyl
po panone, hyda ohe
 pheny dinitophenyl 0
DNP) ketore H
Ne
desivative
Phenylhydva20ne
&yy- NO2
o
+
2,4- dinit CONH)
hydazonc
aldehyde, HCONH H2D
semicaybazone
( 24-
hydazDne NO 421
hydrazineon C= -propanone NH
NNH NN aldinine
Acet
ti H
Ethana)
ca C=
for idenifiND - C
NH
C=
NH
N Ethanal HT NH2
zone
NO) CH3
o used
phenyl (
ide ba
’
compound semicarbaz
car NHNHCONH
c0 Arnmonja
Diri
t NH)NH N02
sem
NH
NH,
-
4o, foms 0C(H)
NH)
NH3'
’foms
ed with
o
of
OYage
C0
Addition Additio Reacion
CHz CH2
H
(a)
()
(e
 (b) Reduction(a) ()
Reductbn REDUCTION :
) ddition A
C-HCH2 - veduced tO
isThe
with
CH3-CO-CH3 aemmensen -CHO R
deld ppanon e Ethanal C=0
Zlnc bonycar
To To
forms
UAlH4 NOBHy
Znt
amalqamand Alcohol:
ConcMe Ho ConcHe sUbstudted
ConcHe tH
Zn Hg
Zn
+ Hydncar
redu bon
Conc
HO H9
Zn
t -CH2qoup
ction -CH,-OH R 1

(RNH2)
amine
treatement
gpoupon o H
’
Conc called
Jm)ne
vene CHa-
CH3 CHa aldehyde R
CH3 CH3-H2
-CH3 ( (schiffs
e+hane C=
We base )
Popane HCe
hydacaybonget N
R+ -
and chiífs
base S
H’0

tone ke
 ())
E+hanal The
KoH phenone
Aceto
wlth olf COcH2
0
In
yeduced
hydazine -Kishney
cay
high bonyl
Conc Zn
He Hqt
CH
NNHC=
to
qooup
bojlinq Reduction
followed-CH,
colvent of
ethylene NNH2 = q0uP
gycol aldehyde
by
aldehyde Ethyl
benzene CH2-CH3
Ethylene
koH,
glycol like
ethyleneheating
CHz-CH
ehane teatemnt and
wi
th ketone
glyco)