Oxygen Contaning Compound

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
Chemistry : Oxygen Containing Compound ®
Pre-Medical
vkWDlhtu ;qDr ;kSfxd (OXYGEN CONTAINING COMPOUND)
1.0 gkbMªkWDlh O;qRiUu (HYDROXY DERIVATIVES)

gkbMªkWDlh O;qRiUu
,fyQsfVd gkbMªkWDlh O;qRiUu ,jksesfVd gkbMªkWDlh O;qRiUu

1.1 ,fyQsfVd gkbMªkWDlh O;qRiUu (Aliphatic Hydroxy Derivatives)
gkbMªkWDlh O;qRiUu ftuesa —OH lh/ks sp3 C ls tqMk gksrk gSA ¼,YdksgkWfyd ;kSfxd½
1.2 ,jksesfVd gkbMªkWDlh O;qRiUu (Aromatic Hydroxy Derivatives)
gkbMªkWDlh O;qRiUu ftuesa —OH lh/ks csathu oy; ds sp2 C ls tqM+k gksrk gSA ¼fQukWfyd ;kSfxd½
,fyQsfVd gkbMªkWDlh O;qRiUu %
®
(a) —OH lewg dh la[;k ds vk/kkj ij oxhZdj.k %
(i) eksuksgkbfMªd [,d –OH] → CH3CH2—OH
(ii) MkbgkbfMªd [nks –OH] → CH2 – CH2
OH OH
(iii) VªkbZgkbfMªd [rhu –OH] → CH2 – CH – CH2

OH OH OH
(iv) ikWyhgkbfMªd [n –OH] → CH2 – CH – CH – CH – CH – CH2

OH OH OH OH OH OH
(b) dkcZu dh izÑfr ds vk/kkj ij oxhZdj.k %

(i) izkFkfed ;k 1° – ,YdksgkWy → CH3CH2 – OH
(ii) f}rh;d ;k 2° – ,YdksgkWy → (CH3)2CH – OH
(iii) r‘rh;d ;k 3° – ,YdksgkWy → (CH3)3C – OH
2.0 eksuksgkbfMªd ,YdksgkWy (MONOHYDRIC ALCOHOL)
2.1 cukus dh lkekU; fof/k;k¡ (General Methods of Preparation)
(i) ,Ydsu ls ¼vkWDlhdj.k }kjk½ %

H⊕ /KMnO
(CH3)3 C—H 
∆
4
→ (CH3)3 C—OH
(ii) ,Ydhu ls %
(a) ty;kstu }kjk %
⊕
H
CH3—CH=CH2 → CH3 – CH – CH3
H2 O
OH
(b) gkbMªkscksjksuhdj.k vkWDlhdj.k }kjk %
(1) BH3 ,THF
CH3—CH=CH2 → 
CH3 – CH2 – CH2 (1° alcohol)
(2) H2 O2 HO
OH
(c) vkWDlheD;wZjhdj.k foeD;wZjhdj.k }kjk %
(i) Hg(OAc)2 , H2 O
CH3—CH=CH2 
(ii) NaBH
→ CH3 – CH – CH3
4
OH
27
®

Chemistry : Oxygen Containing Compound
Pre-Medical
(iii) ,Ydhy gSykbM ls ¼ty vi?kVu }kjk½ %
Aq. KOH
CH3—CH2—Cl  → CH3CH2—OH
or Moist Ag2 O
(iv) dkcksZfuy ;kSfxdksa ls ¼vip;u }kjk½ %

Reducing agent
>C = O → >CH—OH
GOLDEN KEY POINTS
vipk;d inkFkZ gks ldrs gSaA

LiAlH4/H⊕
NaBH4/H⊕
Na + EtOH
Ni/H2
®
LiAlH
R—CHO 
⊕
4
→ R—CH2—OH
H
NaBH
R–C–R 
⊕
4
→ R–CH–R
H
O OH
OD
H
LiAlH4
O D⊕
OH
D
NaBD4
H⊕
LiAlH
CH3—CH=CH—CHO 
⊕
4
→ CH3—CH=CH—CH2—OH
H
ØksVksuSfYMgkbM
(v) bZFkj ls %
dil.H SO
R—O—R 
2 4
→ R—OH + R—OH
dil.H SO
CH3—O—CH2CH3 
2 4
→ CH3—OH + CH3CH2—OH
(vi) vEy vkSj vEy O;qRiUuksa ls ¼vip;u }kjk½%
LiAlH
R—COOH 
⊕
4
→ R—CH2—OH + H2O
H
LiAlH4
R–C–Cl 
⊕
→ R—CH2—OH + HCl
H
O
LiAlH
R–C–OR 
⊕
4
→ R—CH2—OH + R—OH
H
O
LiAlH
R–C–O–C–R 4
→ R—CH2—OH + R—CH2—OH
⊕
H
O O
Note : ,ekbM+ vipf;r gksdj ,ehu cukrs gS ,YdksgkWy ughaA

LiAlH
R–C–NH2 
⊕
4
→ R—CH2—NH2 +H2O
H
O
28

Pre-Medical
(vii) ,LVj ls ¼ty vi?kVu }kjk½%
(a) {kkjh; ty vi?kVu %
NaOH
R–C–OR  
→ R–C–ONa + R–OH
O O
fØ;kfof/k % OH OH

HO 
R–C–OR R–C – OR R – C + RO
(NaOH) (SA) (SB)
O 
O O
⊕ 
Na
R – C–ONa + ROH R – C–O + ROH
O O
(NaOH)
®
CH3–C–OC2H5 CH3–C–ONa + C2H5OH
O O
ty vi?kVu ukfHkdLusgh izfrLFkkiu (NSR) vfHkfØ;k gS vkSj vfHkfØ;k dh dksfV 2 gSA {kkjh; tyvi?kVu
lkcquhdj.k Hkh dgykrk gSA
 Θ
HO
Ph—COOC2H5 → Ph — COO + C2H5OH
(b) vEyh; ty vi?kVu }kjk %
⊕
H
R–C–OR 
 
 R–C–OH + R–OH
H O(excess)
2
O O
⊕
18 Η Ο 18

3
CH3–C–OC2H5  CH3–C–OH + C2H5OH
O O
(viii)p–,ehu ls %
NaNO + HCl(aq.)
R—NH2 
2
→ R—OH + N2
or HNO2
HNO
CH3CH2—NH2 
2
→ CH3CH2—OH + N2
Mechanism :
⊕  ⊕ 
NaNO2 + HCl
CH3 CH2 — NH2  → CH3 CH2 — N2 Cl → CH3 CH2 + N2 + Cl
(vLFkk;h)
H 2O

CH3CH2–OH ¼eq[; mRikn½
Cl CH3CH2–Cl
⊕ 
CH3CH2 O–N=O
CH3CH2–O–N=O + CH3–CH2–NO2
⊕ ¼lg mRikn½
–H CH2 =CH2
CH3–CH2–OH
CH3–CH2–O–CH2–CH3
e/;orhZ dkcZ/kuk;u gksrk gS vr% iqufoZU;kl laHko gSA

29
®

Pre-Medical
Illustrations
NaNO2 + HCl
Illustration 1. CH3CH2CH2—NH2  → ?
Solution. Mechanism :
⊕  ⊕
NaNO2 + HCl
CH3CH2CH2—NH2  → CH3CH2CH2— N2 Cl → CH3 CH2 CH 2
 
HO ⊕ H shift
CH3–CH–CH3 CH3–CH–CH3
rearrangement
OH
HNO2
Exception : CH3–NH2 CH3–O–CH3
®
(ix) xzhU;kj vfHkdeZd ls %
(a) p-,YdksgkWy :
HO
R—MgX + [O] → R—O—MgX →
2
R—OH
[leku C ;qDr p-,YdksgkWy]
R R
−δ +δ
H2O
R MgX C H → H C H → H C H
O OMgX OH [,d C vf/kd ;qDr p-,YdksgkWy]
R R
−δ +δ H2O
R MgX + CH2 CH2→ CH2 CH2 → CH2 CH2
O OMgX OH
[nks C vf/kd ;qDr p-,YdksgkWy]
(b) s-,YdksgkWy %
R R
H2O
R – MgX + R – C – H → R C H → R C H
O OMgX OH
R
R–MgX
R – MgX + H – C – OR → H C R → H C R
H2O
O O OH
(c) t-,YdksgkWy %
R R
H2 O
R – MgX + R – C – R → R C R → R C R
O OMgX OH
R
R–MgX
R – MgX + R – C – OR → R C R → R C R
H2O
O O OH
HkkSfrd xq.k %
(i) C1 ls C11 rd jaxghu æo gSA ysfdu mPprj ,Ydksgy Bksl gSA
(ii) eksuksgkbfMªd ,YdksgkWyksa dk ?kuRo H2O ls de gksrk gSA
(iii) ?kuRo ∝ v.kqHkkj ¼eksuksgkbfMªd ,YdksgkWyksa½ ds fy;s A
30

Pre-Medical
(iv) foys;rk % gkbMªkstu ca/ku ds dkj.k C1 ls C3 vkSj r‘rh;d C;wfVy ,Ydksgy H2O esa iw.kZr;k ?kqyu'khy gksrs gSA
ik’oZ J‘a[kykvksa dh la[;k
foys;rk ∝
v.kqHkkj
foys;rk dk Øe %
C4H9OH > C5H11OH > C6H13OH
CH3
CH3CH2CH2CH2OH < CH3CH2CH–OH < CH3–C–OH
CH3 CH3
CH3CH2CH2 < CH3–CH–CH2 < CH2–CH–CH2
OH OH OH OH OH OH
¼OH dh la[;k c<us ij H-ca/ku c<+rk gS½
®
v.kqHkkj
(v) DoFkukad % DoFkukad ∝
ik’oZ Ja‘[kykvksa dh la[;k
DoFkukad dk Øe % C4H9OH < C5H11OH < C6H13OH
CH3
CH3CH2CH2CH2OH > CH3CH2CH–OH > CH3–C–OH
CH CH3
CH3CH2CH2 < CH3–CH–CH2 < CH2–CH–CH2

OH OH OH OH OH OH
¼OH dh la[;k c<us ij H ca/ku c<+rk gSA½

Illustrations
Illustration 2. ,YdksgkWyksa dk DoFkukad laxr bZFkj ls vf/kd gksrk gSA D;ksa\
Solution. ,YdksgkWy esa H-ca/ku
Illustration 3. ,YdksgkWyksa dk DoFkukad laxr dkcksZfDlfyd vEy ls de gksrk gSA D;ksa\

Solution. dkcksZfDlfyd vEy esa f}yd cuus ds dkj.kA
O H–O
R–C C–R
OH O
2.3 jklk;fud xq.k (Chemical Properties)
eksuksgkbfMªd ,YdksgkWy fuEu vfHkfØ;k n'kkZrs gSaA

(A) vfHkfØ;k,sa ftuesa O – H cU/k dk fo[k.Mu gksrk gSA
(B) vfHkfØ;k,sa ftuesa C – OH cU/k dk fo[k.Mu gksrk gSA
(C) vfHkfØ;k ftuesa iw.kZ ,YdksgkWy v.kq Hkkx ysrk gSA
31
®

Pre-Medical
(A) vfHkfØ;k,sa ftuesa O–H : cU/k dk fo[k.Mu gksrk gS : fØ;k'khyrk Øe ¼vEyh; izÑfr½ gSA
CH3—OH > CH3CH2—OH > (CH3)2CH—OH > (CH3)3C—OH
(i) vEyh; izÑfr %

H2O > R—OH > CH≡CH > NH3 ¼vEyh; lkekF;Z½
,YdksgkWy H2O ls de vEyh; gksrs gS vkSj fyVel ds izfr mnklhu gksrs gS vkSj lfØ; /kkrqvksa (Na, K) ds
lkFk H2 nsrs gSA
1
R—OH + Na → R—ONa + H2
2
1
R—OH + K → R—OK + H2
2
®
(ii) ,fYdyhdj.k %
CH2 N2 ∆
R—OH  → R—O—CH2—H
Na R−X
R—OH  → R—ONa  → R—O—R
¼fofy;elu bZFkj la'ys"k.k½
(iii) ,flfVyhdj.k %
R – OH + Cl – C – R → R – O– C – R
O O
(Acylation)
R – OH + Cl – C – CH3 → R – O– C – CH3
O O
¼,flfVyhdj.k½
OH O–C–CH3
O
COOH CH3 COCl
 → COOH
lsfyflfyd vEy ,lhVkWDlh csUtkWbd vEy

,lhfVy lsfyflfyd vEy
,fLizu ¼nnZ fuokjd o izfrToj ds :i esa mi;ksxh½
(iv) csUtkW;yhdj.k ¼'kkWVu&ckseku vfHkfØ;k½%
R – OH + Cl – C – Ph → R – O– C – Ph
O O
(csatks,yhdj.k)
(v) ,LVjhdj.k %
conc. H SO
R – C – OH + R – OH 
∆
2 4
→ R – C – OR + H2O
O O
lkaæ H2SO4 dks mRizsjd vkSj futZyhdkjd ds :i esa iz;qDr djrs gSaA
32

Pre-Medical
Mechanism :
R ⊕ H
O
⊕ ⊕ ••
H R – OH •
R – C – OH → R – C – OH →
•• R – C – OH
[H2SO4] ••
O O–H O H
R
O H
⊕
R C OR –H2O, –H
R C O
H
O O
H
conc. H2 SO4
Ex. CH3–C– OH + H– OC2H5  ∆
→ CH3 – C – OC2H5 + H2O
O O
®
18 18
conc. H2 SO4
Ex. Ph–C– OH + H– OC2H5  → Ph – C – OC2H5 + H2O
O O
futZyhdkjd ds :i esa 'kq"d HCl dk Hkh mi;ksx fd;k tk ldrk gSA
Ex. CH3–C– OH + H– OC2H5  ∆ →

dry HCl
CH3 – C – OC2H5 + H2O
O O
GOLDEN KEY POINTS

1
 ,LVjhdj.k dh fØ;k'khyrk ∝ .
f=kfoe foU;klh ck/kk
 R – OH dh fØ;k'khyrk ¼;fn vEy leku gS½ % CH3 – OH > 1° > 2° > 3° ,YdksgkWy
 RCOOH dh fØ;k'khyrk ¼;fn ,YdksgkWy leku gS½
CH3
H – C – OH > CH3 – C – OH > CH3 – CH – C – OH > CH3 – C – C – OH
O O CH3 O CH3O
(vi) CH≡CH ds lkFk vfHkfØ;k %
BF /HgO
OCH3
CH ≡ CH + 2CH3—OH 
3
∆ → CH3CH
OCH3
Methylal
BF /HgO
OC2H5
CH ≡ CH + 2CH3CH2— OH 
3
∆ → CH3CH
OC2H5
Ethylal
33
®

Pre-Medical
(vii) dkcksZfuy ;kSfxdksa ds lkFk vfHkfØ;k %
⊕ OR
H → R–CH
R—CHO + 2R—OH 
OR
Acetal
⊕
R OR
H → C
R – C – R + 2R – OH 
R OR
O Ketal
H → ⊕ OCH3
CH3CHO + 2CH3—OH  CH3CH
OCH3
(viii) xzhU;kj vfHkdeZd ds lkFk vfHkfØ;k %
X
R—MgX + H—OR → R – H + Mg
OR
®
(B) vfHkfØ;k,sa ftuesa C OH cU/k dk fo[k.Mu gksrk gS % fØ;k'khyrk Øe ;k {kkjh; izÑfr gSA
CH3—OH < CH3CH2—OH < (CH3)2CH—OH < (CH3)3 C—OH
(i) gSykstu vEyksa ds lkFk vfHkfØ;k %
ZnCl
R—CH2—OH + HCl 
∆ → R—CH2—Cl + H2O
2
vEyksa dh fØ;k'khyrk dk Øe HI > HBr > HCl
(ii) QkLQksjl gSykbM ds lkFk vfHkfØ;k %

3R—OH + PCl3 → 3RCl + H3PO3
R—OH + PCl5 → R—Cl + POCl3 + HCl
(iii) Fkk;ksfuy DyksjkbM (SOCl2) ds lkFk vfHkfØ;k %
Pyridine
R—OH + SOCl2  → R—Cl + SO2 ↑ + HCl
(gas)
(iv) NH3 ds lkFk vfHkfØ;k % ,yqfeuk (Al2O3) dk mi;ksx futZyhdkjd ds :i esa fd;k tkrk gSA
Al O
R – OH + H NH2 
2 3
→ R—NH2 + H2O
250 C

(C) vfHkfØ;k ftuesa iw.kZ ,YdksgkWy v.kq Hkkx ysrk gS %

(i) futZyhdj.k % blesa H2O dk fu"dklu nks izdkj ls gks ldrk gSA
(a) vUrjkf.od vFkkZr nks v.kqvksa ls ,d H2O v.kq dk R;kx ¼bZFkj curk gSA½
(b) vUr% vkf.od vFkkZr ,d ,Ydksgy v.kq ls ,d H2O v.kq dk R;kx ¼,Ydhu curk gSA½
140°C
C2H5–O–C2H5 ¼fofy;elu lrr~ bZFkjhdj.k½
C2H5 – OH + H2SO4
(conc.) 170°C
CH2=CH2 ¼foyksiu½
250°C
C2H5–O–C2H5
C2H5OH + Al2O3
(Alumina) 350°C
CH2=CH2
futZyhdj.k dh lqxerk dk Øe % 3° ROH > 2° ROH > 1° ROH
34

Pre-Medical
(ii) mRizsjdh fogkbMªkstuhdj.k %
Cu
CH3CH2OH 
300° C
→ CH3CHO + H2
¼p- ,YdksgkWy½ ¼,flVSfYMgkbM½
Cu
CH3 – CH – CH3 
300° C
→ CH3 – C – CH3 + H2
OH O
¼s- ,YdksgkWy½ ¼,lhVksu½
CH3 CH3
CH3 C OH Cu
 → CH3 – C = CH2 + H2O
300° C ¼futZyhdj.k½
CH3 ¼vkblks C;wfVyhu½
®
¼r‘rh;d ,YdksgkWy½
(iii) vkWDlhdj.k %
H⊕ KMnO or [O]
R—CH2—OH 
4
→ RCHO 
→ RCOOH
⊕
H /K2 Cr2 O7 Room temp.
¼p- ,YdksgkWy½ ¼leku dkcZu vEy½
[O]
⊕ dksbZ vfHkfØ;k ugha
H⊕/KMnO4 or H /KMnO4 dejs ds rki ij
R–CH–R′ R – C – R′
H⊕/K2Cr2O7
OH O mPp rki
vEy ¼de dkcZu½
(s-,YdksgkWy) ¼leku dkcZu½
R [O]
dksbZ vfHkfØ;k ugha
dejs dk rki
R–C–R
OH mPp rki
vEy ¼de dkcZu½
(t-,YdksgkWy)
[O] [O]
CH3CH2 – CH – CH3 
high temp.
→ CH3CH2 – C – CH3  → CH3COOH + CH3COOH
OH O
dkcksZfuy lewg NksVs ,fYdy lewg ds lkFk tkrk gSA ¼iksiksQ dk fu;e vlefer dhVksu ds vkWDlhdj.k ds
ckjs esa crkrk gSA½
(iv) izkFkfed] f}rh;d o r‘rh;d ,Ydksgyksa esa foHksnu %
(a) Y;wdkl ijh{k.k % lkaæ HCl o futZy ZnCl2 dk feJ.k Y;wdkl vfHkdeZd dgykrk gSA
ZnCl + HCl
p-,YdksgkWy 
2
→ dejs ds rki ij dksbZ vo{ksi ughaA (30 feuV ds vanj xeZ djus ij½
ZnCl + HCl
s-,YdksgkWy 
2
→ /kqa/kykiu 5 - 10 feuV esa B.Ms esa fn[kkbZ nsrh gSA
ZnCl + HCl
t-,YdksgkWy 
2
→ /kqa/kykiu rqjar (2-3 seconds) fn[kkbZ nsrh gSA
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Pre-Medical
(b) foDVj & es;j ijh{k.k %
p-,YdksgkWy → yky jax
s-,YdksgkWy → uhyk jax
t-,YdksgkWy → jaxghu
R—CH2—OH [1°] R2CH—OH [2°] R3C—OH [3°]
P + I2 P + I2 P + I2
R—CH2—I R2CH—I R3C—I
AgNO2 AgNO2 AgNO2
RCH2—NO2 R2CH—NO2 R3C—NO2
®
HNO2 HNO2 HNO2
R – C – NO2 R2C – NO2 No reaction
N–OH N=OH
Nitrolic acid (uhyk) Pseudonitrol (uhyk) jaxghu
NaOH NaOH
Sodium nitrolate (yky) No reaction (uhyk)

(c) MkbZØksesV ijh{k.k %
H⊕ K Cr O
1° Alcohol →
2 2 7
+6
Acid + Cr+3
orange [Cr ]
[gjk]
H⊕ K Cr O
2 2 7
+6
Ketone + Cr+3
orange [Cr ]
[gjk]
⊕
H K Cr O
2 2 7
+6
No oxidation, ¼ukjaxh½
orange [Cr ]
(v) CH3 – OH vkSj C2H5OH es foHksnu %

CH3OH CH3CH2OH
DoFkukad 65°C 78°C
I2 + NaOH vo{ksi ugha CHI3 dk ihyk vo{ksi
Cu/300°C QkesZfyu dh xa/k [HCHO] xa/k ugha

lsfyflfyd vEy foUVjxzhu ds rsy tSlh xa/k xa/k ugha
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OH
CH3OH COOCH3 esfFky lsfyflysV
conc. H2SO4 ; ∆
¼foUVjxzhu rsy dh xa/k ds leku½
OH OH
Ph—OH COOPh esfFky lsfyflysV
COOH
conc. H2SO4
O – C – CH3 lsyksy ¼iwfrjks/kh½
O ,fLifju
CH3COCl COOH ¼nnZfuokkjd ,oa izfrToj ds :i esa½
or Ac2O
BEGINNER'S BOX-1
1. ,sYdksgkWy dh fuEu esa ls fdl vfHkfØ;k esa C–O ca/k dk fo[k.Mu ugha gksrk\
(1) CH3CH2OH + SOCl2 (2) CH3CH(OH)CH3 + PBr3
(3) CH3CH2OH + CH3COOH (4) ROH + HX
®
2. fuEufyf[kr esa ls dkSulk ,sYdsukWy ty esa lokZf/kd foys; gS\
(1) 1–C;wVsukWy (2) 2–C;wVsukWy (3) vkblksC;wfVy ,sYdksgkWy (4) r‘- C;wfVy ,sYdksgkWy
3.
⊕
PCl3 Alc.KOH H3O
CH3CH2CH2–OH → A → B → C
mRikn 'C' gS
(1) CH3CH=CH2 (2) CH3–CH–CH3 (3) CH3–CH–CH3 (4) CH3CH2CH2–Cl
OH Cl
,YdksgkWyksa ds fo"k; esa egRoiw.kZ rF; %

(i) fo"kSykiu [,fFky ,YdksgkWy < vkblksizksfiy ,YdksgkWy < esfFky ,YdksgkWy]
(ii) ifj'kq) ,YdksgkWy % ,fFky ,YdksgkWy 99.5%–100%
(iii) ikWoj ,YdksgkWy % ifj'kksf/kr fLizV + C6H6 + isVªksy dk feJ.k] ikWoj mRié djus ds fy,
(iv) esfFkfyd‘r fLizV % esFksukWy $ fijhMhu $ [kfut uS¶Fkk $ ifj’kksf/kr fLizV
(v) 70% CH3OH dk"B fLizV dgykrk gSA
(vi) 90% C2H5OH ,sYdksgkWy dPpk fLizV dgykrk gSA
(vii) C2H5OH dks rduhdh :i ls ok'k Hkh dgrs gSA
(viii) ifj'kksf/kr fLizV esa 95.5% ,YdksgkWy rFkk 4.5% ty gksrk gSA
GOLDEN KEY POINTS
ijvk;ksfMd vEy HIO4 ;k ySM VsVªk,lhVsV (CH3COO)4Pb ds }kjk vkWDlhdj.k %
HIO
CH2 – CH2 
4

→ HCHO + HCHO
OH OH
(,fFkyhu XykbZdkWy)
CH2 – CH – CH2 HIO4
 
→ HCHO+HCOOH+HCHO
OH OH OH
fXyljksy
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HIO4 ;k (CH3COO)4Pb ds }kjk vkWDlhdj.k ds fy, 'krsaZ %
(i) de ls de 2 —OH ;k 2 >C=O ;k 1-OH rFkk 1 >C=O fofluy dkcZu ij gksA
(ii) ,d HIO4 ,d C—C ca/k rksM+rk gS] rFkk nksuksa dkcZu ij ,d&,d —OH tksM+rk gSA
CH3 OH CH3
2HIO4
CH3—CH—CH—C—CH3 CH3—CH—OH + CH—OH + HO—C—CH3
Ex.
OH OH OH OH OH OH
–3H2O
O
CH3CHO + HCOOH + CH3–C–CH3
O O O
®
Ex.
1HIO4
CH3—C—CH—CH2—C—H CH3—C—OH + HO–CHCH2–C–H
O OH OH
–H2O
CH3COOH + CHO – CH2–CHO
CHO CHO CHO

O
O 2HIO4
O COOH
Ex. –H2O
→ OH + HO—C—OH → +H2O + CO2
O (H2CO3) HO—CH2 CHO
HO—CH2 OH
HO—CH2
OH OH
4.0 ,sjkseSfVd gkbMªkWDlh O;qRiUu (AROMATIC HYDROXY DERIVATIVES)

QhukWfyd ;kSfxd % ;kSfxd ftuesa —OH lewg lh/ks sp2 c [csathu oy;] ls tqM+k gksrk gSA
OH OH OH
CH3 COOH
QhukWy o-fØlkWy lSfyflfyd vEy

OH
OH
OH
OH
OH OH
dsVsdkWy fjlkWflZukWy fDoukWy

lHkh QhukWfyd ;kSfxd mnklhu FeCl3 ds lkFk jaxhu mRikn nsrs gSaA
mnklhu FeCl
Ph—OH 
3
→ cSaxuh jax
mnklhu FeCl
CH3CH2—OH 
3
→ dksbZ jax ugha
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QhukWy (C6H5OH)
QhukWy dks dkcksZfyd vEy Hkh dgrs gSaA QhukWy esa –OH lewg csathu oy; ds sp2 ladfjr dkcZu ls tqM+k gksrk
gSA bldh [kkst :axs (Runge) us dksyrkj ds vklou ds e/; rsy izHkkt ls dh Fkh rFkk bls dkcksZfyd vEy
dkcksZ = dksy; vksfy;e = vkW;y½ uke fn;kA ;g lw{e ek=kk eas ekuo ew=k esa Hkh ik;k tkrk gSA
(1) csUthu lYQksfud vEy ls % tc csUthu lYQksfud vEy ds lksfM;e yo.k dks NaOH ds lkFk laxfyr
djrs gSa rks QhukWy izkIr gksrk gSA
(1) NaOH, ∆ & Pr.
C6H5SO3Na + NaOH 
⊕
→ C6H5OH + Na2SO3
(2) H
(2) csUthu Mkb,stksfu;e yo.k ls % csUthu Mkb,stksfu;e DyksjkbM ds foy;u dks ty ds lkFk xeZ djus ij
®
ukbVªkstu ds fu"dklu ds lkFk QhukWy izkIr gksrk gS %
N2Cl OH
(Steam distilled) H O

∆
2
→ + N2 + HCl
(3) QhukWfyd vEy dk vklou lksMk ykbe ds lkFk djus ij ¼fodkcksZfDlyhdj.k½ %
OH OH
COOH NaOH + CaO

∆
→ + Na2CO3
Salicylic acid
(4) xzhU;kj vfHkdeZd ls % fxzU;kj vfHkdeZd dh fØ;k vkWDlhtu ds lkFk djkus ij izkIr mRikn ds
tyvi?kVu ls QhukWy izkIr gksrk gSA
[O] HO Br
C6H5MgBr  → C6H5OMgBr 
2
→ C6H5OH + Mg
OH
(5) csUthu ls %
OH
VO
+ [O]  →
2 5
300°C
(6) Dyksjks csUthu ls %

Aq. NaOH
Ph—Cl → lkekU; ifjfLFkfr;ksa esa NSR ugha
vuqukn }kjk LFkk;h
Aq. NaOH
R—Cl → R—OH [NSR]
(1) Aq. NaOH, ∆ & Pr

Ph—Cl → Ph—OH [mPp rki ij NSR]
(2) H⊕
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NSR dk Øe %
Cl Cl Cl Cl
NO2 NO2 O2N NO2
< < <
NO2 NO2
Aq. NaOH
300°C & Pr max. –I, –M Aq. NaOH
min. e¯ density 25°
min. ESR
OH max. NSR
OH
O2N NO2
®
NO2
2, 4, 6–Trinitrophenol (Picric acid)
(7) QhukWy dk vkS|kssfxd fuekZ.k % QhukWy dk vkS|ksfxd fuekZ.k fuEu ls fd;k tk ldrk gS %
(a) D;wehu ls
(b) Mkm izØe ls
(a) D;wehu ls ¼vkblksizksfiy csUthu½ % D;wehu dk mRizsjd dh mifLFkfr esa vkWDlhtu ls vkWDlhdj.k djkus
ij D;wehu gkbMªksijkWDlkbM izkIr gksrk gS tks fd ruq H2SO4 }kjk QhukWy rFkk ,lhVksu esa fo?kfVr gks
tkrk gS A
CH3 O–OH
CH3
CH C(CH3)2 OH
O2 H2SO4,H2O
+ CH3–C–CH3
130°C 100°C
Cumene Cumene O
hydroperoxide
(b) Mkm izØe % DyksjkscsUthu ds {kkjh; ty vi?kVu ds i'pkr vEy ls vfHkfØ;k djokus ij QhukWy izkIr
gksrk gS % ¼mijksDr vfHkfØ;k ls vf/kd ek=kk esa QhukWy curk gS½
OH
(1) NaOH,Cu − Fe/300° C

C6H5Cl 
(2) H⊕
→ + NaCl
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BEGINNER'S BOX-2
1. fuEufyf[kr ;kSfxdksa esa ls fdlesa QhukWfyd xq.k ugha gS&
CH—CH3 CH3
(1) (2)
OH
OH
OH CH2OH
(3) (4)
OH OH
2. C6H6O2 v.kqlw=k ls laHkkfor MkbgkfMªd Qhuksyksa dh la[;k fdruh gksrh gS :-

(1) 2 (2) 3 (3) 4 (4) 5
4.2 HkkSfrd xq.k (Physical Properties)
(i) QhukWy ,d jaxghu] fØLVyh; Bksl gSA

(ii) ok;q rFkk izdk'k ds lEidZ esa ;g xqykch jax esa ifjofrZr gks tkrk gSA ¼/khek vkWDlhdj.k½
®
C6H5OH---------- O O --------- HOC6H5
Phenoquinone(pink colour)
(iii) ;g izd‘fr esa fo"kSyk gksrk gS ijUrq bldk mi;ksx iwfrjks/kh rFkk laØe.kgkjh ds :i esa fd;k tkrk gSA
(iv) QhukWy ty esa vkaf'kd foys; ijUrq dkcZfud foyk;dksa esa foys; gksrk gSA
(v) QhukWy dh ty esa foys;rk] ,sfyQsfVd ,YdksgkWyksa ls cgqr de gksrh gS D;kasfd blds v.kq esa gkbMªksdkcZu
Hkkx vfèkd gksrk gSA
(vi) vUrjvkf.od H-cU/ku ds dkj.k Qhuksy dk DoFkukad laxr gkbMªksdkcZu rFkk ,fjy gSykbMksa ls vf/kd
gksrk gSA
(A) —OH lewg ds dkj.k vfHkfØ;k %

(i) vEyh; izd‘fr % QhukWy ,d nqcZy vEy gSA QhukWy dh vEyh; izd‘fr foy;u eas LFkk;h fQukWDlkbM
vk;u ds cuus ds dkj.k gksrh gSA fQukWDlkbM vk;u vuqukn ds dkj.k LFkk;h gksrk gSA _.kkRed vkos'k
dk iw.kZ csUthu fjax esa QSyko ds dkj.k fQukWDlkbM vk;u LFkk;h gksrk gSA bysDVªkWu vkd"khZ lewg
(—NO2, —Cl) fQukWy dh vEyh; izd‘fr c<+krs gSa tcfd bysDVªkWu fod"khZ lewg (—CH3 vkfn ½QhukWy dh
vEyh; izd‘fr ?kVkrs gSaA

 
C6H5OH + H2O 

 C6 H5 O + H3 O
QhukWy] ,sYdksgkWyksa ls vf/kd vEyh; ijUrq dkcksZfDlfyd vEy rFkk dkcksZfud vEy ls de vEyh; gksrk gSA
GOLDEN KEY POINTS
 QhukWy dh vEyh; izd‘fr fuEu esa iznf’kZr gksrh gS %

(i) QhukWy uhys fyVel dks yky dj nsrk gSA
(ii) mPp fo|qr /kuh /kkrq,sa QhukWy ls fØ;k djrh gSA
2C6H5OH + 2Na → 2C6H5ONa + H2
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(iii) QhukWy izcy {kkjksa ls fØ;k djds fQukWDlkWbM cukrk gSA
 ⊕
C6 H5 OH + NaOH → C6 H5 O N a +H2 O
(iv) fQukWy Na2CO3 ;k NaHCO3 dks fo?kfVr ugha djrk gS D;kasfd ;g dkcksZfud vEy ls nqcZy gSA
C6H5OH + Na2CO3 or NaHCO3 → dksbZ vfHkfØ;k ugha
Ph—OH + NaHCO3 
 Ph—ONa + H2CO3
vEy-I {kkj-I {kkj-II vEy -II

vEy − I < vEy − II 
foifjr fn'kk esa vfHkfØ;k
{kkj − I < {kkj − II 
Note : ,lhfVd vEy NaHCO3 ds lkFk fØ;k djrk gS vkSj CO2 xSl ckgj fudkyrk gSA
CH3–C–OH + NaHCO3 
 + H2CO3 [H2O + CO2↑]
®
CH3–C–ONa
O O
vEy -I {kkj -I {kkj -II vEy -II

vEy − I > vEy − II 
vxz fn'kk esa vfHkfØ;k
{kkj − I > {kkj − II 
(ii) PCl5 ls vfHkfØ;k : QhukWy PCl5 ls vfHkfØ;k djds DyksjkscsUthu cukrk gSA POCl3 dk fuekZ.k lgmRikn
ds :i esa gksrk gS tks fQukWy ls vfHkfØ;k djds eq[;r;k VªkbQsfuy QkWLQsV cukrk gSA
∆
C6H5OH + PCl5  → C6H5Cl + POCl3 + HCl
3C6H5OH + POCl3 → (C6H5)3PO4 + 3HCl
(iii) Zn pw.kZ ls vfHkfØ;k : QhukWy dh fØ;k Zn pw.kZ ls djkus ij csUthu izkIr gksrh gSA
∆
C6H5OH + Zn  → C6H6 + ZnO
Illustrations
Illustration 4. fuEu esa ls dkSu&dkSuls ;kSfxdksa esa Zn ds lkFk xeZ djus ij vkWDlhdj.k laHko gS &
CH3
CH2OH OH
(I) (II)
CH3 COOH
CH2—OH OH
(III) (IV)
(1) I, II, III (2) I, III, IV (3) II, IV (4) II, III
Solution Ans.(3) ;g QhukWfyd ;kSfxdksa esa laHko gSA
(iv) NH3 ls fØ;k % QhukWy futZy ZnCl2 dh mifLFkfr esa NH3 ls fØ;k djds ,sfuyhu cukrk gSA
Anhydrous ZnCl2 or (NH4 )2 SO3 /NH3 150°C
C6H5OH + NH3 → C6H5NH2 + H2O
300°C
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(v) FeCl3 ls fØ;k % QhukWy FeCl foy;u ¼mnklhu½ ds lkFk fØ;k djds ,d ladqy ds cuus ds dkj.k cSaxuh jax nsrk gSA
3
C H OH + FeCl → cSaxuh jax

6 5 3
bl vfHkfØ;k dk mi;ksx QhukWy rFkk ,Ydksgy ds foHksnu esa fd;k tkrk gSA
(vi) ,sflyhdj.k % QhukWy {kkjh; foy;u dh mifLFkfr esa ,sflM DyksjkbM ;k ,ugkbMªkbM ls fØ;k djds
Qsfuy ,LVj cukrk gSA
NaOH
C6H5OH + ClCOCH3  → C6H5O—C—CH3
− HCl
O
(vii) csUtkW;yhdj.k ('kksVu&ckseku vfHkfØ;k)
NaOH
C6H5OH + Cl—C—C6H5  → C6H5O—C—C6H5
− HCl
O O
(B) csUthu fjax dh vfHkfØ;k,sa % —OH lewg vkFkksZ rFkk iSjk funsZ'kh gS ;g csUthu fjax dks lfØ; djrk gSA
(i) gsykstuhdj.k % QhukWy CCl4 dh mifLFkfr esa czksehu ls fØ;k djds o-rFkk p-czkseks QhukWy dk feJ.k cukrk gSA
®
OH OH OH
CHCl or CS or CCl
Br
+ Br2  →
3 2 4
low.temp. +
Br
(Major)
QhukWy czksehu ty ds vkf/kD; ls fØ;k djds 2, 4, 6–Vªkbczkseks QhukWy dk 'osr vo{ksi nsrk gSA ¼QhukWy dk ifj{k.k½
OH OH
H O Br Br
+ 3Br2 → + 3HBr
2
Br
(ii) ukbVªhdj.k % QhukWy 0-100 C ij ruq HNO3 ls fØ;k djds o-rFkk p-ukbVªksQhukWy cukrk gSA
OH OH OH
dil.HNO NO2
 3
→
0 −10°C +
NO2
QhukWy dh fØ;k ukbVªhdkjd feJ.k ls djkus ij 2, 4, 6–VªkbukbVªks QhukWy ¼fifØd vEy½ curk gSA ysfdu ;g
fifØd vEy cukus dh vPNh fof/k ugha gS D;ksafd ukbfVªd vEy QhukWy dks p-csatksDohuksu esa vkWDlhd‘r dj nsrk gSA
OH OH
Conc.HNO3 NO2 NO2
 → 2, 4, 6-VªkbukbVªks QhukWy ¼fifØd vEy½
Conc.H SO2 4
NO2
(iii) lYQksuhdj.k % QhukWy] lkUnz H2SO4 ls fofHkUu rki ij fØ;k djds o-rFkk p-gkbMªkWDlhcsUthu lYQksfud
vEyksa dk feJ.k cukrk gSA
OH
SO3H
OH 25°C
+ conc. H2SO4 OH
100°C
SO3H
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(iv) fÝMsy Øk¶V vfHkfØ;k % QhukWy dh fØ;k futZy AlCl3 dh mifLFkfr esa esfFky DyksjkbM ls djkus ij p-
Øhlksy eq[; mRikn izkIr gksrk gSA
OH OH
OH CH3
Anhydrous AlCl

3
→ +
+ CH3Cl
CH3
o-Øhlksy p- Øhlksy (Major)
OH OH OH
COCH3
Anhydrous AlCl
+ CH3COCl 
3
→ +
COCH3
o – vkSj p – gkbMªkWDlh ,lhVksQhukWu
(v) xkVjeku ,sfYMgkbM la'ys"k.k % QhukWy dh fØ;k futZy AlCl3 dh mifLFkfr esa nzo HCN rFkk HCl xSl ls
®
djkus ij eq[;r;k p-gkbMªkWDlh csUtsfYMgkbM curk gS ¼QkfeZyhdj.k½
AlCl
HCl + HCN 
3
→ HN=CHCl
OH OH
OH
AlCl H O

− HCl 
3
→ →2
− NH
+ HN=CHCl 3
CH=NH CHO
(vi) jkbej Vheku vfHkfØ;k% QhukWy dh fØ;k DyksjksQkWeZ rFkk tyh; NaOH ls djkdj cus mRikn dk vEyh; ty
vi?kVu djkus ij o–gkbMªkWDlh csUtsfYMgkbM curk gSA tc CCl4 ysrs gSa rks lSfyflfyd vEy curk gSA
ONa ONa + OH
CHCl3 NaOH H
OH → →
60°C NaOH (aq.) H2O
CHCl2 CHO CHO
Salicylaldehyde
CCl4 ONa ONa OH

NaOH H +
60°C NaOH (aq.)
→ →
CCl3 COONa H2O
COOH
Salicylic acid
(vii) dksYcsf'eV vfHkfØ;k% bl vfHkfØ;k esa 1400 C ij C6H5OH dh fØ;k CO2 vkSj NaOH ls djkus ij cus
mRikn dk vEyh; ty vi?kVu djkus ij lSfyflfyd vEy curk gSA
OH ONa OH
NaOH, 140° C COONa + COOH

H
+ CO2 → →
6 atm. pressure
lksfM;e lSfyflysV lSfyflysd vEy

(viii) gkbMªkstuhdj.k% 1500 C - 2000 C rki ij QhukWy dk gkbMªkstuhdj.k Ni dh mifLFkfr esa djkus ij
lkbDyksgsDlsukWy curk gSA
OH
OH
CH OH
Ni H2C CH2
+ 3H2 →
150 – 200° C
or
H2C CH2
CH2 (vPNk foyk;d)
lkbDyksgsDlsukWy (C H 6 OH)
11
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Pre-Medical
(ix) Ýhl iqufoZU;kl vfHkfØ;k%
fijhfMu → C H OCOCH
C6H5OH + CH3COCl  6 5 3
Phenyl Acetate
OH OH
COCH3
anhydrous AlCl3
C6H5OCOCH3 → +
Qsfuy ,flVsV (,LVj)

COCH3
(x) ;qXeu vfHkfØ;k,as % QhukWy {kkjh; foy;u dh mifLFkfr esa csUthu Mkb&,stksfu;e DyksjkbM ls ;qfXer
gksdj ,d Mkb (p-gkbMªkWDlh ,stkscsUthu½ cukrk gS ¼ukjaxh jatd½A
NaOH
®
N2Cl + OH → N N OH
–HCl
p– gkbMªkWDlh,stkscsUthu (ukjaxh jatd)
QhukWy lkUnz H2SO4 dh mifLFkfr esa FkSfyd ,ugkbMªkbM ls ;qfXer gksdj ,d jatd ¼Qhuks¶Fksyhu½ cukrk
gS ftldk lwpd ds :i esa mi;ksx fd;k tkrk gSA
O O OH
O=C C=O H OH O=C C
H2SO4
+ → OH
–H2O
H OH
FkSSfyd ,ugkbMªkbM QhukWy (nks v.kq) Qhuks¶Fksyhu (vEyh; ek/;e esa jaxghu
rFkk {kkjh; ek/;e eas xqykch jax)
(xi) ysMjj&eukls ¼QkeZ,fYMgkbM ls la?kuu½ vfHkfØ;k % QhukWy] HCHO ds vkf/kD; ls NaOH ;k nqcZy
vEy (H+) dh mifLFkfr esa fØ;k djds cSdkykbV ¼jsftu½ cgqyd cukrk gSA
OH OH OH
NaOH CH2OH
+ HCHO → +
CH2OH HCHO ds lkFk la?kuu

Ckgqyhdj.k
HO CH2 OH
CH2 CH2
OH CH2 OH
CH2 CH2
cSdkykbV cgqyd (QhukWy QkeZfYMgkbM jsftu)
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Pre-Medical
(xii) ,slhVksu ls fØ;k % ¼,slhVksu ds lkFk la?kuu½
OH OH OH OH
con. H2SO4
→
–H2O
H H CH3—C—CH3
O fcl&fQukWy A
p-p'– vkblks izksfiyhMhu MkbQhukWy
CH3—C—CH3
(xiii) Oxidation:
Air [O]
O O + H2O csUtksDohuksu ¼xqykch½
CrO2Cl2
OH
(O)
®
(Phenol
K2S2O8/KOH
HO OH (fDoukWy)
(,Ycl ijlYQsV vfHkfØ;k)
csUthu–1, 4–MkbZvkWy
BEGINNER'S BOX-3
1. jkbej&Vheku QkWfeZyhdj.k vfHkfØ;k esa %&

(1) DyksjksQkWeZ dk QhukWDlkbM vk;u ij ;ksx gksrk gSA
(2) VªkbDyksjksesfFky dkcZ_.kk;u dk QhukWDlkbM ij ;ksx gksrk gSA
(3) MkbDyksjksdkchZu dk QhukWDlkbM vk;u ij ;ksx gksrk gSA
(4) gkbMªkWDlkbM vk;u dk QhukWy ij ;ksx gksrk gSA
2. QhukWy rFkk csUthu MkbZ,tksfu;e DyksjkbM foy;u dh fØ;k ls cus mRikn dh lajpuk D;k gksrh gS\
(1) HO N=N Cl (2) N=N OH
(3) N—N (4) N=N Cl
OH Cl
NaNO2 H O
3. QhukWYk  → gjk jax 
2
→ yky jax NaOH
 
→ uhyk jax
lkanz H2 SO4
;g vfHkfØ;k fdlds uke ls fofnr gS\
(1) xkVjeku (2) gkWQeku (3) yhcjeku (4) jkbej&Vheku
Qhuksy dk ijh{k.k %
(1) QhukWy uhys fyVel dks yky dj nsrk gSA
(2) QhukWy dk tyh; foy;u ,d cwan FeCl3 ds lkFk cSaxuh jax nsrk gSA
(3) QhukWy yhcjeku ukbVªkslks ijh{k.k nsrk gSA
(4) QhukWy dk tyh; foy;u czksehu ty ds lkFk 2, 4, 6&VªkbczkseksQhukWy dk 'osr vo{ksi nsrk gSA
(5) QhukWy] FkSfyd ,ugkbMªkbM ls lkUnz H2SO4 dh mifLFkfr esa fØ;k djds Qhuks¶Fksyhu nsrk gS tks {kkj ds
lkFk xqykch jax nsrk gSA
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Pre-Medical
QhukWy rFkk ,sYdksgkWy ¼,sFksuksy½ esa vlekurk,sa %
(1) fQukWDlkbM vk;u esa vuqukn ds dkj.k QhukWy ,fyQSfVd ,YdksgkWy dh vis{kk vf/kd vEyh; gksrk gSA
(2) QhukWy FeCl3 ds lkFk cSaxuh jax nsrk gS tcfd ,sfyQsfVd ,sYdksgkWy ugha nsrk gSA
(3) QhukWy PCl5 ds lkFk VªkbQsfuy QkWLQsV cukrk gS tcfd ,YdksgkWy ugha nsrk gSA
(4) QhukWy vkWDlhd‘r gksdj Dohuksu cukrk gS tcfd ,sYdksgkWy] ,sfYMgkbM ;k dhVksu rFkk vEy cukrk gSA
QhukWy ds mi;ksx %
(1) lkcqu rFkk yks'ku esa ,sfUVlsfIVd ¼iwfrjks/kh½ ds :i esa rFkk MsVkWy ¼DyksjkstkbZyhukWy vkSj VfiZukWy dk
feJ.k½A
(2) ,stksMkb] fQuks¶Fksyhu] fifØd vEy ¼foLQksVd½] lkbDyks gsDlsuksy ¼jcj dk foyk;d½] IykfLVd
¼csdsykbV½ vkfn ds fuekZ.k esaA
(3) ,sfLizu] lsyksy] QsukflVhu vkfn nokbZ;ksa ds fuekZ.k esaA
(4) L;kgh ds fy, ifjj{kdA
®
5.0 bZFkj (ETHER)
R–O–R (Mkb,fYdy bZFkj),,YdkWDlh ,YdsuA budk lkekU; lw=k CnH2n + 2O gksrk gSA
CH3–O–CH2CH3 (esFkkWDlh ,Fksu) ;k ,fFky esfFky bZFkj
bZFkj] R–OH dk eksuks ,fYdy O;qRié rFkk H2O dk M+kb,fYdy O;qRié gSA
−H −2H
R—OH 
+R
→ R—O—R ←
+2R
 H—O—H
oxhZdj.k % bZFkj dks fuEu izdkj ls oxhZd‘r fd;k x;k gS %

(a) ljy ;k lefer bZFkj e.g. R–O–R
(b) fefJr ;k vlefer bZFkj e.g. R–O–R'
lajpuk :
: O: Sp ladfjr
3
bZFkj dk v.kq vkWDlhtu ijek.kq ij bysDVªksuksa ds ,dy ;qXeksa ds dkj.k >qdk
ca/k σ 110° σ ca/k gqvk gksrk gS cU/k dks.k 110° dk gksrk gSA ;g H2O ds v.kq ds cU/k dks.k
R R
105° ls vf/kd gS D;ksafd blesa Hkkjh ,fYdy lewgksa ds chp izfrd"kZ.k gS tks H- ijek.kqvksa dh vis{kk vf/kd gSA
>qdh lajpuk dh otg ls blesa f}/kqzo vk/kw.kZ gksrk gS vr% v.kq /kzqoh; gksrk gSA
(a) ,fYdy gSykbM ls %
(i) fofy;elu la'ys"k.k }kjk %
R—X + NaO—R → R—O—R + NaX [SN2 Reaction]
Ex. CH3—CH2—Cl + CH3—ONa → CH3—CH2O—CH3 + NaCl
CH3 CH2
Ex. CH3—C—Cl + CH3ONa H3C—C 3° RX ls bZFkj cukuk laHko ugh gSA

CH3 CH3
(Major)
CH3 CH3
∆
Ex. CH3—C—ONa + CH3—CH2—Cl → CH3—C—O—CH2—CH3
CH3 CH3
Ex. CH2=CH—Cl + CH3CH2—ONa → dksbZ vfHkfØ;k ughaA
[vuqukn izHkko }kjk LFkk;h]
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Pre-Medical
∆
(ii) 'kq"d Ag2O ls vfHkfØ;k% 2RX + Ag O 2 → R—O—R + 2AgX
∆
Ex. 2CH3—CH2—Cl + Ag2O → CH3CH2OCH2CH3 + 2AgCl
(b) R–OH ls :
Con. H2 SO4
(i) f}v.kqd futZyhdj.k }kjk : R—OH ∆ → R—O—R
Mechanism :
..
.. H
⊕ ⊕ H R O
.. H
⊕
–H
⊕
.. H → R O
R O 
–H2O
R O R → R—O—R
H
H
250°C 140°C
CH3CH2–O–CH2CH3 CH3CH2—O–CH2CH3
Al O conc. H2SO4 (Williamson's continuous
®
←
2 3 CH3–CH2–OH →
ether synthesis)
350°C 170°C
CH2=CH2 CH2=CH2
(Elimination)
(ii) CH2N2ds lkFk vfHkfØ;k ¼MkbZ ,stksesFksu½%

∆
R—OH + CH2N2 
BF → R—O—CH2—H + N2
3
(i) CH3OCH3 , CH3OCH2CH3 xSl gS tcfd mPprj lnL; ok"i'khy æo gSaA

(ii) bZFkj de /kqzoh; gSA
(iii) bZFkj] ty esa de foys; gSA
(iv) bZFkj dk DoFkukad leko;oh ,YdksgkWy dh vis{kk de gksrs gSA
Illustrations
Illustration 5. bZFkj H2O esa de ?kqyu'khy gS] D;ksa\
Solution. vèkzqoh; gksus ds dkj.k ;g H2O ds lkFk nqcZy H–ca/k cukrk gSA
5.3 jklk;fud xq.k (Chemical properties)
bZ F kj de /kq z o h; gS vr% de fØ;k'khy gS A bZ F kj] lfØ; /kkrq v ks a tS l s [Na,K] vkfn ls fØ;k ugha djrs
gS A bZ F kj] Ba Ms ] ruq vEy] vkWD lhdkjd rFkk vipk;d ds lkFk fØ;k ugha djrs gS A ;s lfØ;
fØ;kRed lew g ugha j[krs gS a A
(1) {kkjh; xq.k % vkWDlhtu ijek.kq ij ,dkdh bysDVªkWu ;qXe dh mifLFkfr ds dkj.k bZFkj yqbl {kkj dh Hkk¡fr
dk;Z djrk gSA bZFkj] BaMs lkUæ vEy ls fØ;k djds vkWDlksfu;e yo.k cukrs gSaA
.. cold ; conc. HCl

⊕
O C2H5 Cl

Ex. C2H5OC  C2H5 Mkb,fFky vkWDlksfu;e DyksjkbM+
.. 2H5
H
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Pre-Medical
..
cold ; conc. ⊕ 
Ex. C2H5—O—C
.. 2H5 →
H SO
C2H5–O–C2H5 HSO4 Mkb,fFky vkWDlksfu;e gkbMªkstu lYQsV
2 4
H
bZFkj] yqbZl vEy tSls BF3, AlCl3, RMgX ds lkFk milgla;kstd ca/k cukrk gSA
R •• R
O
••
R F
Ex. • ••
O• B F R—Mg—X [xzhU;kj vfHkdeZd ds fy, bZFkj foyk;d ds :i esa dke djrk gS]
R F
••
O
••
R R
(2) ijkWDlkbM dk fuekZ.k % bZFkj ok;qe.Myh; vkWDlhtu ;k vkstksukbM vkWDlhtu ls tqM+ tkrk gSA eqä
ewyd fØ;kfof/k] e/;orhZ eqä ewyd gksrk gSA
®
C2H5—O—C2H5 O (nonpolar)
 CH3CH2—O—CHCH3
Long contact →
2
sunlight or UV O—O—H
.. .. ..
.. 2H5 + : O
C2H5OC .. 2H5 or (C2H5)2O → O
.. → C2H5OC
↓
..
:O
.. :
H
O O2
CH3CH2—O—CH2—Ph
→ 2
long contact
CH3—CH2—O—CH—Ph CH3—CH2—O—CH—Ph
O—O—H
ijkWDlkbM vLFkk;h rFkk foLQksVd gksrs gSaA.
GOLDEN KEY POINTS

ijkWDlkbM ds fy;s ijh{k.k %
FeSO /KCNS 4
bZFkj (ijkWDlkbM) Ykky jax
Fe +3 CNS Fe(CNS)3
bZFkj (ijkWDlkbM) + Fe +2
(yky)
heat
(3) PCl5ds lkFk vfHkfØ;k: ROR + PCl 5  → 2RCl + POCl3
Re d P + HI
(4) vip;u : CH3CH2OCH2CH3 
heat
→ 2CH3CH3
(5) HX ds lkFk vfHkfØ;k : R–O–R' + HI → R–OH + R'–I

bZFkj ds mi;ksx %
(i) lkekU; fu'psrd ¼General aneasthetic) ds :i esa
(ii) olk] rsy] jsftu] xzhU;kj vfHkdeZd ds foyk;d ds :i eas A
(iii) dkcZfud vfHkfØ;k ds fy, vfØ; rFkk futZy ek/;e cukus esa mnkgj.k oqVZ~t vfHkfØ;k
(iv) Ñf=ke lqxa/k cukus esa
(v) Mkbvkblksizksfiy bZFkj&isVªksy esa viLQksVujks/kh ds :i esa
(vi) ,Ydksgy rFkk bZFkj ds feJ.k dks isVªksy ds LFkku ij dke esa ysrs gSaA ftldk O;kikfjd uke ÞuSVsykbVÞ gSA
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Pre-Medical
6.0 dkcksZfuy ;kSfxd (CARBONYL COMPOUNDS)
dkcZfud ;kSfxd ftuesa C=O lewg mifLFkr gksrk gS dkcksZfuy ;kSfxd dgykrs gSaA C=O lewg dks
dkcksZfuy lewg dgrs gSaA budk lkekU; lw=k Cn H2nO (n = 1, 2, 3......) gksrk gSA dkcksZfuy ;kSfxdksa dks nks lewgksa
esa ckaVk x;k gSA
O
(a) ,fYMgkbM % ,fYMgkbM –C–H lewg gksrk gS ¼bls QkWfeZy lewg Hkh dgrs gSa½ ;g fØ;kRed lewg ,d
O
1°
la;kstd gksrk gSA – C – H lewg dk dkcZu 10 izd‘fr dk gksrk gSA i.e. R–C=O
H
(b) dhVksu % bldk dkcksZfuy lewg C=O dhVksfud lewg dgykrk gS] ;fn bldh nksuksa eqDr la;kstdrk;sa
®
,fYdy lewg ls la;ksftr gksrh gSA ;g ,d f}la;kstd lewg gksrk gSA
R 2°
C=O dk dkcZu 2° izd‘fr dk gksrk gSA i.e C=O
R
dhVksu dk oxhZdj.k fuEu izdkj ls gS %

R
(i) ljy vFkok lefer dhVksu% buesa nksuksa ,fYdy lewg leku gksrs gSaA C=O
R
R
(ii) fefJr ;k vlefer dhVksu% buesa mifLFkr nksauksa ,fYdy lewg esa fHkUurk gksrh gSA C=O
R′
Ex. ¼dhVksu½ : lefer vlefer

CH3 CH3CH2
C=O C=O
CH3 CH3
¼,lhVksu ;k MkbZesfFky dhVksu½ ¼,fFky esfFky dhVksu½

izksisukWu C;wVsukWu
O O O O
•• •• •• ••
Sp. Point : C OH, C X, C NH2, C OR
Åij fy[ks bu lHkh ;kSfxdksa esa bysDVªkWu ;qXe o f}vkcU/k la;qfXer gksrs gSA
O
O ||
•• vr% vuqukn gksrk gSA bu ;kSfxdksa esa –C – dkcksZfuy lewg gksrk gS rc Hkh ;s dkcksZfuy ;kSfxd ugha
C Z
gksrs] D;ksafd budh yk{kf.kd vfHkfØ;k,a dkcksZfuy lewg ls fHkUu gksrh gSA
Lkjapuk : C=O ;kSfxdksa esa dkcZu dk sp2 ladj.k gksrk gSA ;s nks σ cU/k vkSj ,d π cUèk cukrk gSA dkcZu
ijek.kq dk vladfjr ijek.kq d{kd ,oa vkWDlhtu ds 2p d{kd ¼lekUrj½ C=O lewg esa π cUèk cukrk gSA
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Pre-Medical
C sp2
σ C—C—O / H—C—O esa ca/k dks.k 1200 dk gksrk gSA
C =π O
C
C o O ijek.kq esa fo|qr _.krk esa vUrj ds dkj.k C=O lewg /kzqoh; gksrs gSaA
δ+ δ–
C=O vr% ,fYMgkbM o dhVksu dk dqN u dqN f}/kqzo vk?kw.kZ gksrk gSA
(A) ,fYMgkbM vkSj dhVksu nksuksa ds fy,

(1) ,YdksgkWy ds vkWDlhdj.k }kjk%
(a) By K2Cr2O7 / H2SO4 }kjk : izkFkfed ,YdksgkWy ds vkWDlhdj.k ls ,fYMgkbM ,oa f}rh;d
®
,YdksgkWy ds vkWDlhdj.k ls dhVksu curs gSaA (K2Cr2O7 / H2SO4) ,d izcy vkWDlhdkjd gSA
[O]
RCH2OH → RCHO (,fYMgkbM)
K2 Cr2 O7 / H2 SO4 (dil.)
[O]
R–CH–R  → R–C–R (dhVksu)
K2 Cr2 O7 / H2 SO4
OH O
,fYMgkbM ’kh?kz gh iqu% vkWDlhd‘r gksdj ,flM esa ifjofrZr gks tkrk gSA
[O] [O]
RCH2OH 
→ R—CHO 
→ R—COOH
vr% izkFkfed ,Ydksgy dk vkWDlhdj.k] ,fYMgkbM ds DoFkukad ls Hkh mPp rki ij fd;k tkrk gS]
ftlls ,fYMgkbM ok"ihd‘r gksdj i‘Fkd gks tkrs gSa vkSj vkWDlhdj.k ls cp tkrs gSaA
(b) ean vkWDlhdkjd % CrO3 / fijhMhu, ¼dksfyu vfHkdeZd½;k P.C.C. (fijhMhfu;e Dyksjks ØksesV] CrO3 +
C5H5N + HCl) 1° ,Ydksgy dks ,fYMgkbM rFkk 2° ,Ydksgy dks dhVksu esa vkWDlhd‘r djrs gSaA
RCH2OH + [O] → RCHO + H2O
bl vfHkfØ;k ls ,fYMgkbM mPp yfC/k esa izkIr fd;k tk ldrk gSA

(2) ,Ydksgyksa ds fogkbMªkstuhdj.k }kjk %
Cu
CH3CH2OH 
300°C
→ CH3CHO ¼,lhVSfYMgkbM½
O
Cu
CH3–CHCH3  → CH3–C–CH3
300°C ¼,lhVksu½
OH
CH3 CH2
Cu
CH3–C–OH  → CH3–C+H2O
300°C ¼vkblksC;wfVyhu½
CH3 CH3
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(3) dkcksZfDlfyd vEy ds Ca-yo.kksa ds 'kq"d vklou }kjk %
O O
R—C—O Ca+Ca O C H ∆
→ 2RCHO + 2CaCO3
R—C—O O C H
O O
dSfY'k;e ,Ydsuks,V dSfY'k;e QkWesZV ( R–C–R vkSj HCHO Hkh curk gSA½
O
H COO ∆
Ca → HCHO + CaCO3
HCO O
R COO ∆
R
→ C = O + CaCO3
®
Ca
RCO O R
dSfY'k;e ,Ydsuks,V dhVksu

QkfeZd vEy ds vykok vU; lHkh vyx&vyx vEyksa ds dSfY'k;e yo.k lkFk esa xeZ djus ij vlefer
dhVksu dk fuekZ.k djrs gSaA
O O
∆
R COO O C R' → 2R–C–R′ + 2CaCO3
Ca + Ca
R CO O O C R' dhVksu
O
,sfFky essfFky dhVksu cukus ds fy, dSfY'k;e ,lhVsV ,oa dSfY'k;e izksfi;ksusV dk iz;ksx fd;k tkrk gSA
O O
CH3
∆
CH3 CO O C CH2CH3 → 2 C = O + 2CaCO3
Ca+Ca
CH3 C O O C CH2CH3 C2H5
O O
dSfY'k;e ,lhVsV dSfY'k;e izksfi;ksusV ,fFky esfFky dhVksu

(4) dkcksZfDlfyd vEyksa ds rki vi?kVu }kjk %tc dkcksZfDlfyd vEyksa dh ok"i MnO/3000C ij izokfgr
dh tkrh gS rks dkcksZfuy ;kSfxd curs gSA
H COOH MnO

300°C
→ HCHO + H2O + CO2
HCO OH
CH3CO OH MnO
 → CH3
300°C C=O + CO2 + H2O
CH3 COOH CH3
MnO
RCO OH  →
300°C RCHO + CO2 + H2O
H COOH
MnO
RCO OH  →
300°C RCOR' + CO2 + H2O
R' COOH
52
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Pre-Medical
(5) tSe&MkbZgSykbMksa ds ty vi?kVu ls % VfeZuy ¼varLFk½ tSe & MkbZgSykbM ty vi?kVu ds }kjk
,fYMgkbM nsrs gSa tcfd vU; ¼e/;orhZ tSe MkbgSykbM½ dhVksu cukrs gSaA
Cl KOH(aq) OH −H O
CH3CH  → [ CH3CH ] 
2
→ CH3CHO
Cl OH
VfeZuy tSe MkbZgSykbM vLFkk;h ,flVSfYMgkbM

O
Cl
OH
→ CH3 C CH3
− H2 O
CH3 C CH3 KOH(aq)
 → 
CH3 C CH3 ,lhVksu
Cl
ukWu VfeZuy tSeMkbZgSykbM OH
vLFkk;h
(6) MkbZ vkWy ds vkWDlhdj.k ls % fofLkuy MkbZ vkWy ij vk;ksfMd vEy ;k ySMVsVªk ,lhVsV ¼CH3 COO)4 Pb
®
ds lkFk vkWDlhÑr gksdj dkcksZfuy ;kSfxd cukrk gSA
R—CH—CH—R′ + HIO4 → RCHO + R'CHO + HIO3 + H2O
OH OH
R R O O
R—C—C—R′ + HIO4 → R—C—R + R′—C—R + HIO3 + H2O
OH OH
(7) ,Ydhu ds vkstksuh vi?kVu }kjk % bl vfHkfØ;k dk mi;ksx ,Ydhu esa f}cU/k dh fLFkfr tkuus ds fy,
fd;k tkrk gSA
O O
H O/Zn
RCH=CH2 + O3 → RCH CH2 → RCHO + HCHO
2
–ZnO
Ozone O
Ozonide
O O
H2O/Zn
R—C=CH2 + O3 → R—C CH2 → R—C=O + HCHO
–ZnO
R O R
R
(8) ,Ydkbuksa }kjk %

(a) ty;kstu % 1% HgSO4 o ruq H2SO4 ds lkFk 60-80°C ij
O
dil.H2 SO4 pyko;ork 

CH≡CH + H2O → [CH2=CHOH]  CH3—C—H
Hg+2
vU; ,Ydkbu eq[;r% dhVksu cukrs gSa %

H2SO4 Pkyko;ork
CH3C CH + H2O +2 CH3—C=CH2 CH3—C—CH3
Hg
OH O
¼bZukWy½
53
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Pre-Medical
(b) gkbMªks cksjkuu % B2H6, (BH3)2 ;k R2BH ds lkFk fØ;k }kjk ,fYdfuy MkbZ,fYdy cksjsu nsrs gSA
1– ,Ydkbu → ,fYMgkbM
vU; ,Ydkbu → dhVksu
+δ –δ H2O2
R—C ≡ CH + R2BH R—CH = CHBR2 RCH = CHOH
OH¯ Tautomerism
R—CH2—C—H + R2BOH
O
HO
CH3—C ≡ C—CH3 + R2BH → CH3—CH=C—CH3 
2 2
OH –
→
BR2


CH3—CH=C—CH3  CH3—CH2—C—CH3
OH O
®
(B) dsoy ,fYMgkbM ds fy,
(1) jkstueq.M vip;u }kjk %
Pd
RCOCl + H2  → RCHO → RCH2OH
Pd/BaSO4
RCOCl + H2  → RCHO + HCl
BaSO4 ,fYMgkbM dk vkSj vkxs ,YdksgkWy esa vip;u gksus ls jksdrk gSA
bl fof/k ls QkWeZfYMgkbM dk fuekZ.k ugha fd;k tk ldrkA
Pd/BaSO4
Ex. C2H5COCl + H2  → C2H5CHO + HCl
izksfivksfuy DyksjkbM izksisuy
(2) LVhQu vip;u }kjk %
SnCl2 /HCl H2 O
R—C≡N+2H  → R—CH=NH  → RCHO+NH3
SnCl2 /HCl H2 O
C2H5—C≡N + 2[H] → C2H5CH=NH  → C2H5CHO + NH3
(C) dsoy dhVksuksa ds fy,
(1) xzhU;kj vfHkdeZd }kjk %
X
RMgX + R—C≡N → R—C=NMgX 2H2 O
 → R—C=O + NH3 + Mg
OH
R R
O O
RMgX + R—C—Cl R—C—R
(Limited)
O O
∆
RMgX + R—C—OR R—C—R+ ROMgX
(Limited)
(2) MkbZ,fYdy dsM~fe;e }kjk % R'CdR' ¼MkbZ,fYdy dsMfe;e½ ,d dkcZ/kkfRod ;kSfxd gSA
RCOCl + R'CdR' → RCOR' + R'CdCl
;g vfHkfØ;k xzhU;kj vfHkdeZd ls mÙke gS D;ksafd mlesa xzhU;kj vfHkdeZd dhVksu ls vkSj vkxs vfHkfØ;k
djds 30 ,Ydksgy cukrk gSA
C2H5 CH3 C2H5
Cd → C=O+ Cd
Ex. CH3COCl + Cl
C2H5 C2H5
54
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Pre-Medical
voLFkk % dsoy QkWeZfYMgkbM gh xSl gS] vkSj C11 rd lHkh dkcksZfuy ;kSfxd nzo gS rFkk C12 o mlls mPp
dkcksZfuy ;kSfxd Bksl gSA
foys;rk : C1 ls C3 ¼QkeZfYMgkbM] ,flVsfYMgkbM vkSj izksfivksusfYMgkbM½ rFkk ,lhVksu ty esa eqDr :i ls
δ+ δ–
foys; gSA bldk dkj.k gS C=O cU/k dh /kzqork ftlds dkj.k ty ds v.kq ds lkFk gkbMªkstu cU/ku laHko
gSA C5 o mPp ;kSfxd ty esa vfoys; gSA
δ+
H
δ+ δ– δ+ 1
C=O H – Oδ– foys;rk ∝
v.kqHkkj
H-bonding
®
DoFkukad: DoFkukad ∝ v.kqHkkj
DoFkukad dk Øe % - ,YdksgkWy > dhVksu >,fYMgkbM > ,Ydsu ¼leku v.kqHkkj½

bldk dkj.k gS fd ,Ydksgy esa vUrj vkf.od gkbMªkstu cU/k mifLFkr gSA ysfdu dkcksZfuy ;kSfxdksa ds v.kqvksa
ds e/; H-cU/k vuqifLFkr gksrk gSA blds LFkku ij nqcZy f}/kzqo&f}/kzqo oUMjoky vkd"kZ.k cy mifLFkr gksrk
gSA ,Ydsu v/kzqoh; gksrs gSA
δ+ δ– δ+ δ–
C=O C=O
?kuRo % dkcksZfuy ;kSfxdksa dk ?kuRo ty dh vis{kk de gksrk gSA

BEGINNER'S BOX-4
1. ,flM] C=O lewg dh vfHkfØ;k;sa ugha n'kkZrs] bldk dkj.k gS
(1) f}ydhdj.k (2) vuqukn
(3) pØh; lajpuk (4) tqM+k gqvk ,fYdy ewyd
2. ,d ;kSfxd dk ok"i ?kuRo 44 gS rks bldk v.kqlw=k gksxk %&
(1) C2H5O (2) C3H6O2 (3) C4H10O (4) C5H12O
3. 23 xzke lksfM;e esfFky ,sYdksgy ls fØ;k djus ij nsrk gS&

(1) vk/kk eksy H2 (2) ,d eksy H2 (3) ,d eksy O2 (4) dksbZ ugha
dkcksZfuy ;kSfxd fuEu vfHkfØ;k,a iznf'kZr djrs gSa&

6.3.1 ukfHkd Lusgh ;ksxkRed vfHkfØ;k,s
6.3.2 vU; vfHkfØ;k,s
6.3.3 dsoy ,fYMgkbM dh vfHkfØ;k,s
6.3.4 dsoy dhVksu dh vfHkfØ;k,s
55
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Pre-Medical
6.3.2 vU; vfHkfØ;k,¡
(a) vip;u % mRikn dh izd‘fr dke esa fy, x;s vipk;d ij fuHkZj djrh gSA
(i) C = O → CH fuEu vipk;d gks ldrs gSa
2
 Red P/HI at 150°C

 Zn-Hg/HCl ¼DyhesUlu vip;u½
Θ
 (i) N2H4 (ii) O H / ∆ ¼oksYQ fd'uj vip;u½
(ii) C = O → CHOH fuEu vipk;d gks ldrs gSa
 /kkrq (Metal) + H2
 LiAlH4
 NaBH4
Na + C2H5OH
®

(b) PCl5 vkSj SOCl2 ds lkFk vfHkfØ;k :

Cl
C = O + PCl5 → C + POCl3
Cl
QkLQksjl isUVk DyksjkbM

Cl
C = O + SOCl2 → C + SO2
Cl
Fkk;ksfuy DyksjkbM
(c) ,YMksy la?kuu % ,sls dkcksZfuy ;kSfxd ftuesa α-H ijek.kq gksrk gS] ruq NaOH ds lkFk la?kuu
(Condensation) djds ,YMksy (aldol) nsrs gSaA ,YMksy esa ,YdksgkWfyd vkSj dkcksZfuy nksuksa lewg gksrs gSa] tks
{kkjh; ek/;e esa xeZ djus ij α, β-vlar‘Ir dkcksZfuy ;kSfxd esa ifjofrZr gksrs gSaA
–
dil OH/∆
CH3—CH + HCH2CHO → CH3—CH—CH—CHO →
–H O
NaOH
CH3—CH=CH—CHO
2
OH H ØksVkssuSsfYMgkbM
O
,YMksy la?kuu dh fØ;kfof/k % ;g fuEu nks inksa esa gksrh gS

(i) dkcZ_.kk;u dk cuuk
(ii) dkcZ_.kk;u dk nwljs ,fYMgkbM v.kq ds lkFk tqM+uk
(i) dkcsZuk;u dk cuuk : C=O dk α-H ijek.kq i;kZIr vEyh; gksrk gS] tks {kkj }kjk izksVksu ds :i esa
ljyrk ls fudy tkrk gSA
δ+ δ−
OH + H – CH2 – C – H CH2 – C – H + H2O
O O
{kkj ,sflVsfYMgkbM dkcZ_.kk;u
bl rjg fufeZr dkcsZuk;u vuqukn (Resonance) ds dkj.k LFkk;h gksrk gSA
CH2—C—H ←→ CH2=C—H
O O
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Pre-Medical
(ii) dkcZ_.kk;u dk nwljs ,fYMgkbM v.kq ds lkFk ;ksx %
O H O–
–
CH3–C + CH2–C=O CH3– C – CH2 – CHO
H H
Aldehyde H2O
(other molecule)
OH H O
–
CH3 – C – CH2 – C = O → CH3 – CH = CH – CH
OH/∆
α, β–vlar‘Ir ,sfYMgkbM
H
Aldol
®
leku dkcksZfuy ;kSfxd → ljy ,YMksy la?kuu
fHkUu dkcksZfuy ;kSfxd → fefJr ;k ØkWl ,YMksy la?kuu
ljy la?kuu %
CH3 O CH3
∆
CH3–C–CH3 + H–CH2–C–CH3 → CH3–C–CH2–C → CH3–C=CH–COCH3 + H2O
O O OH CH3 esflfVy vkWDlkbM ;k

4–esfFky– 3–isUVhu– 2–vkWu
fefJr ;k ØkWl ,YMksy la?kuu %
Weak (2)ljy
CH3CH + CH3–C–CH3 → dqy (4) mRikn
Base (2) fefJr
O O
;g vfHkfØ;k ,YMksy la?kuu vfHkfØ;k dgykrh gSA mijksDr vfHkfØ;k ds fefJr ,YMksy la?kuu mRikn gSaA
α  –
OH OH/ ∆
CH3–CH+CH2–COCH3 → CH3–CH–CH2–COCH3 → CH3–CH=CH–COCH3
Weak base –H2O
O H OH
(Aldol)
CH3 CH3 CH3

α  –
OH OH/ ∆
CH3–C+CH2–CHO → CH3–C–CH2–CHO → CH3–C=CH–CHO
Weak base –H2O
O H OH
(Aldol)
57
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Pre-Medical
Illustrations
OH 
Illustration 7. CH3CHO + CH3CH2CHO 
(WB) 
→P dqy 4 mRiknA mRiknksa dh lajpuk fyf[k, \
Θ
OH O H/ ∆ 
Solution. CH3–CH + CH2CHO  → (Aldol) 
–H2 O
→ CH3—CH=CH—CHO
O H
Θ
α  OH O H/ ∆
CH3–CH2–CH+CH2–CHO  → (Aldol) 
–H2 O
→ CH3—CH2—CH=CH—CHO
O H
CH3
CH3 Θ
α  OH
CH3–CH+CH–CHO → (Aldol) 
 –H2 O
→ CH3–CH=C–CHO O H/ ∆
O H
®
CH3 CH3
Θ
α  OH O H/ ∆
→ (Aldol) 
CH3–CH2–CH+CH–CHO  –H2 O
→ CH3–CH2–CH=C–CHO
O H
GOLDEN KEY POINTS

 ;fn fefJr ,YMkWy la?kuu vfHkfØ;k esa ,d gh dkckZsfuy ;kSfxd esa α–H ijek.kq gks rks dqy nks mRikn gh izkIr
gksaxsA

CH3CHO + C6H5CHO OH
→ dqy 2 mRikn
( WB )
α Θ
OH O H/ ∆
CH3–CH + CH2–CHO  → (Aldol) 
–H2 O
→ CH3 — CH = CH — CHO
(ØksVksu ,fYMgkbM)
O H
α
Θ
OH  O H/ ∆
C6H5–CH + CH2–CHO  → (Aldol) 
–H2 O
→ C6H5 — CH = CH — CHO
(flusesfYMgkbM)
O H
 vUr% v.kqd ,YMkWy la?kuu %
 
OH
CH3–C–CH2–CH2–C–CH3 → CH3–C–CH2–CH2–C–CH2
(–H2O)
O O O O
O ←
OH/∆ H3C O H3C O
H3C HO
–H O ←
2

HO
2
O
(α, β-Unsaturated Ketone) (Aldol)
;gk¡ rhu lnL;h oy; dk ,d vkSj mRikn Hkh çkIr gksrk gS] ijUrq rhu lnL;h oy; dh vis{kk ikap lnL;h
oy; vf/kd LFkk;h gS] vr% mä mRikn gh eq[; mRikn gksrk gSA
58
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Pre-Medical
(d) vkWDlhdj.k %
(i) K2Cr2O7/H2SO4 }kjk % vkDlhdj.k ls 10 ,YdksgkWy ,fYMgkbM nsrs gSa tks vkSj vf/kd vkDlhd‘r gksdj
leku C- ijek.kq okys vEy nsrs gSa] vxj 20 ,YdksgkWy dks mPp rki ij KMnO4/H⊕ dh mifLFkfr esa
vkWDlhÑr fd;k tk;s rks ;g de dkcZu okys vEy dk fuekZ.k djrk gSA
[O] [O]
R—CH2OH  → R—CH = O  → R—COOH
(1° ,Ydksgy) leku dkcZu ;qDr vEy

[O] [O]
CH3CH2CH2–CH–CH3 CH3CH2CH2–C–CH3 CH3CH2COOH+CH3COOH
OH O de dkcZu ;qDr vEy
(ii) SeO2 ¼flfyfu;e MkbZvkDlkbM½ }kjk vkDlhdj.k % dhVksu ;k ,fYMgkbM flfyfu;e vkDlkbM ls
®
vkDlhd‘r gksdj MkbZ dkcksZfuy ;kSfxd cukrs gSaA ;g vfHkfØ;k dsoy α—CH2— bZdkbZ ijek.kq okys
dkcksZfuy ;kSfxdksa esa gh lEHko gSA
HCHO bl vfHkfØ;k dks ugha n'kkZrsA

α
∆
CH3CHO + SeO2 → H–C–C–H + Se + H2O
O O
XykbvkWDlsy
α ∆
CH3–C–CH3 + SeO2 → CH3–C–C–H + Se + H2O
O O O
esfFky XykbvkWDlsy¼ikb:oSfYMgkbM½
6.3.3 dsoy ,fYMgkbM dh vfHkfØ;k,a :
(a) dSfutkjks vfHkfØ;k % os ,fYMgkbM ftuesa α - H ijek.kq ugha gksrk lkanz NaOH o KOH ds lkFk ;g
vfHkfØ;k nsrs gS] mRikn dkcksZfDlfyd vEy dk yo.k o ,YdksgkWy cukrs gSA
bl vfHkfØ;k esa dkcksZfuy ;kSfxd dk ,d v.kq vEy esa vkDlhd‘r gks tkrk gS rFkk nwljk v.kq ,YdksgkWy
esa vipf;r gks tkrk gSA bl izdkj dh vfHkfØ;k,sa jsMksDl vfHkfØ;k,a dgykrh gSA
Conc.
HCHO + HCHO  → HCOONa + CH3OH
NaOH,∆
dSfutkjks vfHkfØ;k esa ç;qDr fØ;kfof/k :
(a) OH dk HCHO ds v.kq ij rhoz mRØe.kh; ;kstu

OH

OH
H–C–H H–C–H

O O
59
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Pre-Medical

(b) gkbMªkbM vk;u H dk HCHO ds nwljs v.kq dh vksj foLFkkiu
OH O OH O
H–C– H + C–H H–C+H–C–H
O H O H

QkWfeZd esFkkWDlkbM
vEy vk;u
izksVksu fofue;
(c) izksVksu fofue;
H C OH + CH3O → HCOO + CH3OH

 
®
O
HCOO + Na⊕ → HCOONa
tc v.kq leku gS rks → ljy dSfutkjks vfHkfØ;k ¼fo"kehdj.k vfHkfØ;k ½

tc v.kq fo"ke gS rks → fefJr dSfutkjks vfHkfØ;k ¼jsMkWDl vfHkfØ;k ½
fefJr dSfutkjks vfHkfØ;k esa vf/kd fØ;k’khy ,fYMgkbM vkDlhd‘r rFkk de fØ;k’khy vipf;r gksrk gSA
NaOH
HCHO + C6H5CHO 
∆
→ HCOONa + C6H5CH2OH
¼vkDlhd‘r½ ¼vipf;r½
lksfM;e QkesZV csfUty ,Ydksgy
(b) fV'kSUdks vfHkfØ;k % ;g dSfutkjks vfHkfØ;k dk gh cnyk gqvk :i gSA bl vfHkfØ;k dks lHkh ,fYMgkbM
(C2H5O)3 Al, dh mifLFkfr esa nsrs gS vkSj ,LVj cukrs gSA
O
(R 'O )3 Al
2RCHO →∆
RCH2—O—C—R
,LVj
(C2 H5 O)3 Al
Ex. CH3 CHO + CH3 CHO 
→ CH3 COOH + CH3 CH2 OH
  
,LVjhdj.k↓
CH3—COOCH2CH3 (,fFky ,flVsV)
(c) vipk;d xq.k % ,fYMgkbM ljyrk ls vkDlhd‘r gks tkrs gSa blfy, ;s izcy vipk;d gksrs gaSA
(i) VkWysu vfHkdeZd % ;g ,fYMgkbM dks vkDlhd‘r djrk gSA VkWysu vfHkdeZd ,d veksuhd‘r flYoj
ukbVªsV foy;u gSA
(AgNO3+NH4OH) → [Ag(NH3)2]OH
Θ
RCHO+[Ag(NH3)2]OH → RCOO + Ag + H2O
jtr niZ.k
AgNO3 + NH4OH → AgOH → Ag2O
Θ
RCHO + Ag2O → RCOO + Ag ↓ (jtr niZ.k)
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Pre-Medical
(ii) Qsgfyax foy;u % ;g CuSO4, NaOH vkSj lksfM;e iksVsf'k;e VkVZjsV dk feJ.k gSA
Qsgfyax foy;u A– (aq.) CuSO4 dk foy;u
Qsgfyax foy;u B– jkslsy yo.k ¼lksfM;e iksVsf'k;e VkVZjsV + NaOH)
Qsgfyax foy;u A + Qsgfyax foy;u B– ¼D;qfizd VkVZjsV dk xgjk uhyk jax½
Θ Θ
RCHO + Cu + OH → RCOO + Cu2O
+2
¼D;wizl vkWDlkbM& yky vo{ksi½

Cu2+ →
+
Cu
¼D;wfizd& uhyk½ ¼D;wizl& yky vo{ksi½

(iii) csusfMDV foy;u % ;g CuSO4 + lksfM;e lkbVªsV + Na2CO3 dk feJ.k gSA ;g Cu+2 nsrk gS rFkk ;g
®
,fYMgkbM }kjk vipf;r gksdj D;wizl vkWDlkbM dk yky vo{ksi nsrk gSA
Θ
RCHO + Cu + OH →
2+ –
RCOO + Cu2O
¼D;wizl vkWDlkbM& yky vo{ksi½

(iv) f'kQ vfHkdeZd % f'kQ vfHkdeZd p-jkstsusfyu gkbMªksDyksjkbM ;k estsUVk jatd dk ruq foy;u gSA
;g xqykch jax dk jatd gS vkSj bls f'kQ jatd Hkh dgk tkrk gSA
bldk xqykch jax SO2 izokfgr djus ls jaxghu gks tkrk gS rFkk ;g f'kQ vfHkdeZd dgykrk gSA
,fYMgkbM f'kQ vfHkdeZd ds xqykch jax dks iqu% ykrs gSA
6.3.4 dsoy dhVksuksa dh vfHkfØ;k,s
(1) vip;u % ,lhVksu] esXuhf'k;e veyxe vkSj ty ls vipf;r gksdj fiukdksy nsrk gSA
CH3 CH3
CH3 CH3 Mg–Hg
C=O + O = C → CH3–C—C–CH3
water
CH3 CH3
OH OH
fiukdksy
(2) DyksjksQkWeZ ds lkFk vfHkfØ;k %
CH3 OH
CH3
C=O + CHCl3 → C
CH3 CH3 CCl3
(DyksjhVksu)
(lEeksgd)
(3) vkWDlhdj.k vfHkfØ;k % iksiksQ fu;e (popoff's rule) ds vuqlkj C=O lewg NksVs ,fYdy lewg ds
lkFk jgrk gSA
O
[O]
CH3–CH2–C–CH3  → CH3COOH + CH3COOH
61
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Pre-Medical
BEGINNER'S BOX-5
1. Vksysu vfHkdeZd ls fØ;k djus esa leFkZ ;kSfxd gS&
(1) QkeZ,fYMgkbM (2) QkfeZd vEy (3) ,sflV ,fYMgkbM (4) mijksDr lHkh
2. ,slhVSfYMgkbM rFkk NaOH ds tyh; foy;u dh fØ;k dk mRikn D;k gS %&

OH H
(1) CH3–CH2–CH–C=O
OH H
(2) CH3–CH–CH2–C=O
(3) CH3–CH–C–CH3
®
OH O
(4) CH2–CH2–CH2–C=O
OH H
3. Qsfyax foy;u gksrk gS %&

(1) estsUVk jatd dk foy;u ftls SO2 }kjk fojaftr dj fn;k x;k gksA
(2) veksfu;ke; AgNO3 foy;u
(3) dkWfLVd lksMk rFkk lksfM;e iksVsf'k;e VkVZjsV ;qDr CuSO4 foy;u
(4) 2, 4 – MkbukbVªksQsfuygkbMªsthu dk ,sYdksgkWyh foy;u
7.0 csatsfYMgkbM ¼dM+os cknke dk rsy] dM+os cknke dk ?kVd½

[BENZALDEHYDE (C6H5CHO)] [OIL OF BITTER ALMONDS (COMPONENT OF BITTER ALMOND]
CO/ HCl + ZnCl2

C6H6 *(xkWVjeku dksp vfHkfØ;k)
(1) CrO2Cl2 (2) H2O
C6H5CH3 *¼,VkMZ vfHkfØ;k½
Pd/BaSO4
C6H5COCl *¼jkstsueq.M vfHkfØ;k½
(i) SnCl2/HCl (ii) H2O
C6H5CN *¼LVhQu vfHkfØ;k½
(HCOO)2Ca/∆
(C6H5COO)2Ca
C6H5CHO
aq. KOH
C6H5CHCl2
[O] ¼fu;af=kr vkWDlhdj.k½
C6H5CH2OH
HCOOC2H5
C6H5MgBr
(1) HCN/HCl + ZnCl2
C6H6 (2) H2O
¼xkWVjeku ,fYMgkbM vfHkfØ;k½
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Pre-Medical
C6H5CH(OH)CN
HCN
NaHSO3
C6H5CH(OH)SO3Na
NH2—Z C6H5CHO
C6H5CH=N–Z C6H5—CH—C—C6H5 ¼csatksbZu la?kuu½
alc.KCN
OH O ¼csatksbZu½
Red P + HI
C6H5CH3
(CH3CO)2O,CH3COONa C H —CH=CH—COOH
6 5
C6H5COOH
Oxidation
(flUusfed vEy) (ikfdZu vfHkfØ;k)
HNO3/H2SO4
PCl5 C6H5CHO m – ukbVªkscsatSfYMgkbM
C6H5CHCl2
Fuming H2SO4
m–QkfeZy casthu lYQksfud vEy
Tollen
jtr niZ.k ijh{k.k
®
reagent
Cl2/FeCl3
m–Dyksjks csatsfYMgkbM
C6H5COONa+C6H5CH2–OH NaOH
CH3–C–CH3
dSfutkjks vfHkfØ;k
O
C6H5CH=N—Ar Ar—NH2  C6H5CH=CH—C—CH3 (,YMksy la?kuu)
OH/∆
f'kQ {kkj O
Schiff's
xqykch jax reagent
OH
(1)C6H5MgBr
C6H5—CH—C6H5 (2) H2O
8.0 dkcksZfDlfyd vEy (CARBOXYLIC ACID)
O
||
dkcZfud ;kSfxd ftuesa dkcksZfDlfyd (–COOH) lewg ik;k tkrk gSA ;g fØ;kRed lewg dkcksZfuy ( –C – )o
gkbMªksfDly (—OH) lewg ds la;ksx ls curk gSA

O O
|| ||
–C – + —OH → –C – OH
dkcksZfuy lewg gkbMªkWDlh lewg dkcksZfDlfyd lewg

dkcksZfDlfyd lewg dh fof'k"Vrk;sa bu nks lewg dk ljy ;ksx u gksdj Lo;a fof'k"V gksrh gSA dkckZsfDlfyd
vEyksa dk vEyh; LoHkko buesa mifLFkr ¼izfrLFkkiuh;½ H – ijek.kq ds dkj.k gksrk gSA budk lkekU; lw=k
CnH2nO2 gksrk gSA
oxhZdj.k (Classification) :
eksuksdkcksZfDlfyd vEy (RCOOH) : os vEy ftuesa dsoy ,d dkcksZfDlfyd lewg ik;k tkrk gS & bUgsa ,d
{kkjdh vEy Hkh dgrs gSA
lkekU; lw=k - CnH2nO2 ( n = 1, 2, 3.......) mPp eksuksa dkcksZfDlfyd vEy olh; vEy dgykrs gSA
Ex. CH3COOH ,lhfVd vEy
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Pre-Medical
MkbZdkcksZfDlfyd vEy - nks dkcksZfDlfyd lewg okys dkckZsfDlfyd vEy] bUgsa f}{kkjdh vEy Hkh dgrs gSA
COOH
Ex. vkWDlsfyd vEy
COOH
VªkbZdkcksZfDlfyd vEy % rhu dkcksZfDlfyd lewg okys dkckZsfDlfyd bUgsa f=k{kkjdh vEy Hkh dgrs gSA
CH2COOH
Ex. HO–C–COOH flfVªd vEy
CH2COOH
lajpuk % –COOH lewg dk dkcZu ijek.kq sp2 ladfjr gksrk gS vkSj bl C- ijek.kq ij cus cU/k dks.kksa dk
eku 1200 gksrk gSA
®
8.1.1 ,Ydksgy o dkcksZfuy ;kSfxdkssa ds vkWDlhdj.k }kjk % vkWDlhdj.k vEyh; K2Cr2O7 ;k KMnO4 dh mifLFkfr esa
fd;k tkrk gSA

[O] [O]
RCH2OH →
K Cr O / H SO
RCHO  → RCOOH
2 2 7 2 4
,Ydsu ds vkWDlhdj.k esa r‘rh; mRikn ds :i esa vEy curs gSA

[O] [O] [O]
R—H  → R—OH  → R—CHO  → R—COOH
GOLDEN KEY POINTS

 ,fYMgkbM vkWDlhdj.k djus ds QyLo:i leku- dkcZu la[;k okys vEy nsrs gSaA
 dhVksu vkWDlhdj.k djus ij de C ijek.kq okys vEy nsrs gSaA
 dhVksu ds vkWDlhdj.k gsrq bUgsa yEcs le; rd çcy vkWDlhdkjd ds lEidZ esa j[krs gSA
8.1.2 ,fYdy lk;ukbMksa o ukbVªkbyksa ds tyvi?kVu }kjk % vEyh; ek/;e (dil. HCl) eas iw.kZ ty vi?kVu gksrk gSA
{kkjh; ek/;e esa vkaf'kd ty vi?kVu gksrk gSA
OH O O
O/H H2 ⊕
Tautomerism H2O/H⊕
R—C≡N → R—C=NH R—C—NH2 → R—C—OH+NH3
8.1.3 1, 1, 1 - VªkbZ gsyks ,Ydsu ds {kkjh; tyvi?kVu }kjk %

Cl OH
R—C Cl + 3KOH → KOH HCl
–3KCl R—C O H → RCOOK + H2O → RCOOH + KCl
–H2O
Cl OH
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Pre-Medical
8.1.4 vEyh; O;qRiéksa ds ty vi?kVu }kjk %
O O
R—C—Z + H—OH → R—C—OH + HZ
Z —Cl, —OCOR, —OR, —NH2
vEy O;qRiéksa dh fØ;k'khyrk dk Øe % RCOCl > (RCO)2 O > RCOOR > RCONH2
HOH
RCOCl 
dil.acid
→ RCOOH + HCl
HOH
(RCO)2O 
dil.acid
→ 2RCOOH
HOH
RCOOR' 
dil.acid
→ RCOOH + R'OH
HOH
R—CONH2 
dil.acid
→ RCOOH + NH3
®
8.1.5 xzhU;kj vfHkdeZd }kjk %
O O
X
H2O
RMgX + O = C = O → R—C—OMgX → R—C—OH + Mg
OH
dkcZu-MkbZvkWDlkbM
Bksl CO2('kq"d cQZ) iz;qä dh tkrh gSA
C1—C4 dkcksZfDlfyd vEy iw.kZ :i ls ty esa feJ.kh; gksrs gSaA

1
foys;rk ∝
v.kqHkkj
ty ds v.kq ds lkFk vUrj vk.kfod gkbMªkstu cU/k ds dkj.k ;s ty esa foys; gksrs gSaA
DoFkukad: DoFkukad rFkk xyukad ∝ v.kqHkkj
vEy > ,YdksgkWy

bldk dkj.k ;s gS fd vEyksa esa nks vkWDlhtu ijek.kq gkbMªkstu ca/k esa Hkkx ysrs gS ¼tcfd ,Ydksgy esa dsoy ,d vkWDlhtu½
ok"i ;k foy;u voLFkk esa fuEurj vEy fdUrq æo voLFkk esa ;s cgqyd (Polymer) ds :i esa jgrs gS
f}yd ds :i esa ik;s tkrs gSA

O H O O R C O O H
R C C R
O H O R C O H O H O C R
xyukad % le la[;k esa dkcZu ijek.kq okys vEyksa ds xyukad fo"ke la[;k esa dkcZu ijek.kq okys vEyksa ls
vf/kd gksrs gSaA le la[;k dkcZu okys vEyksa dk dkcksZfDly o varLFk esfFky lewg foijhr fljksa ij jgdj
fØLVy tkyd dh ladqyu {kerk c<+krs gSaA ftlls buds xyukad mPp gksrs gSA
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Pre-Medical
8.3.1 –COOH lewg ds H ijek.kq ds dkj.k gksus okyh vfHkfØ;k,s %

(a) vEyh; xq.k %

O O O
••  ⊕
R—C—O—H R—C—O + H ←→ R—C=O (Carboxylate ion, Conjugate base)
dkcksZDlysV vk;u vuqukn }kjk LFkkbZd‘r gks tkrk gS vr% dkcksZfDlfyd vEy vEyh; xq.k iznf’kZr djrs
gSA ,Ydksgyksa esa ,YdksDlkbM LFkkbZd‘r ugh gks ikrs vr% os mnklhu jgrs gSA
R—OH 

 R − OΘ + H +
,YdksDlkbM vk;u
(a) dkckZsfDlfyd vEy uhys fyVel dks yky dj nsrs gSA
®
(b) NaHCO3 ds tyh; ?kksy esa feyk;s tkus ij ;s vEy CO2 xSl ds cqycqys NksM+rs gSA
RCOOH + NaHCO3 → RCOONa + H2O + CO2 ↑
(c) {kkjksa ls fØ;k djds yo.k cukrs gS

RCOOH + NaOH → RCOONa + H2O
RCOOH + Ca(OH)2 → (RCOO)2Ca + H2O
(d) /kkrqvksa ls fØ;k

RCOOH + Na → RCOONa + ½H2
HCOOH > CH 3 COOH > C 2 H 5 COOH

vEyh; xq.k dk Øe gS %
CCl 3 COOH > HCCl 2 COOH > CH 2 Cl COOH > CH 3 COOH
buds vEyh; xq.kksa dks izsjf.kd izHkko o vuqukn ds vk/kkj ij le>k;k tk ldrk gSA
(b) CH2N2 ls vfHkfØ;k % bl fof/k ls dsoy esfFky ,LVj dk fuekZ.k fd;k tk ldrk gSA
RCOOH + CH2N2 → RCOOCH3 + N2
esfFky ,LVj
8.3.2 –OH lewg ds dkj.k vfHkfØ;k,sa %
(a) ,LVjhdj.k %
Conc.H SO
CH3COOH + HOC2H5 
2 4
→ CH3COOC2H5 + H2O
(b) NH3 ls fØ;k %

∆ P O /∆
CH3COOH + NH3 → CH3COONH4 → 2 5
CH3CONH2 → CH3CN
(c) Fkk;ksfuy DyksjkbM ls fØ;k %

Pyridine
CH3COOH + SOCl2  → CH3COCl + SO2 ↑ + HCl
(d) PCl5 ls fØ;k %

CH3COOH + PCl5 → CH3COCl + POCl3 + HCl
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Pre-Medical
(e) P2O5 (futZyhdkjd½ ls vfHkfØ;k %
CH3CO OH P O or CH3CO
→
2 5
O + H2O
CH3COO H lkanz H2SO4 ∆ CH3CO
HCOOH dk futZyhdj.k lkUæ H2SO4 }kjk fd;k tkrk gS

Conc.H SO
HCOOH 
2 4
→ CO + [H2O.H2SO4]
O
||
8.3.3 –COOH – lewg ds –C – ds dkj.k vfHkfØ;k,sa %
LiAlH4
(a) CH3—COOH + 4H  → CH3CH2OH + H2O
Ni/ ∆
(b) R—COOH + 3H2  → R—CH2—OH + H2O
®
O
Re d P
(c) R C OH + 6HI 
& mPp nkc → R—CH3 + 2H2O + 3I2
8.3.4 –COOH lewg ds dkj.k vfHkfØ;k %

(a) fodkcksZDlhdj.k %
∆
CH3COONa + NaOH / CaO  → CH4 + Na2CO3
(lksMkykbe)
(b) dksYcs fo|qr vi?kVu %
CH3COONa oS|qr vi?kVu CH3 + CO + NaOH + H

2 2
CH3COONa (tyh;) CH3
(c) gqULMhdj vfHkfØ;k %

CCl4
CH3COOAg + Br2 →
hν
CH3Br + AgBr + CO2
or Cl2 or CH3Cl + AgCl + CO2
(d) dkcksZfuy ;kSfxdksa dk fuekZ.k %

∆
(CH3COO)2Ca → CH3COCH3
∆
'kq"d vklou
(HCOO)2Ca → HCHO
MnO
2HCOOH → HCHO
MnO mRizSjdh; vip;u
2CH3COOH → CH3COCH3
(e) f'eV vfHkfØ;k % bl izdkj izkIr ,ehu esa fØ;kdkjd vEy ls ,d C ijek.kq de gksrk gSA
(1) H SO
RCOOH + N3H  2
(2) H2 O
4
→ RNH2 + CO2 + N2
gkbMªstksbd vEy
67
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Pre-Medical
8.3.5 ,fYdy (R) lewg ds dkj.k vfHkfØ;k,sa %
(a) gSykstuhdj.k [HVZ vfHkfØ;k] [gSy OgksykMZ ftysUldh vfHkfØ;k] : bl vfHkfØ;k esa α- H ijek.kq
gSykstu }kjk foLFkkfir fd;s tkrs gSA
P P/Cl P/Cl
CH3COOH + Cl2 → ClCH2COOH 
2
→ Cl2CHCOOH 
2
→ Cl3CCOOH
GOLDEN KEY POINTS

HCOOH o CH3COOH ds fy;s ijh{k.k
ijh{k.k HCOOH CH3COOH
1. vipk;d xq.k
vipk;d inkFkZ
®
VkWysu vfHkdeZd jtr niZ.k 
Qsgfyax foy;u Cu2O yky 
K2Cr2O7 Cr+3 gjk 
2. fodkcksZDlhdj.k Na2CO3 + H2 CH4
QkfeZd vEy ds mi;ksx %

(i) ,d iwfrjks/kh ds :i esa
(ii) Qy&laj{k.k esa
(iii) peZ 'kks/ku esa
(iv) lwrh rFkk Åuh diM+k jaxkbZ m|ksx esa
,lhfVd vEy ds mi;ksx %
(i) fljds (6 to 10%) ds :i esa @ pVuh] vkpkj] eqjCcs cukus esaA
(ii) jcM+ {khj (ysVDl) ls jcM+ rFkk nw/k ls dslhu ds fuekZ.k esa Ldanudkjh ds :i esa
(iii) ,d foyk;d ,oa iz;ksx'kkyk vfHkdeZd ds :i esa
9.0 csatksbd vEy [BENZOIC ACID (C6H5COOH)]
9.1 cukus dh lkekU; fof/k;k¡ (General Method of Preparation) :

[O]
C6H5CHO
+
H /KMnO4
C6H5CH3 +
H3O
C6H5CN +
(i) aq. KOH (ii) H
C6H5CCl3
(i) CO2 (ii) H2O
C6H5MgBr
Zn C6H5COOH
H–O C6H4COOH
∆
(o, m, p)
H2O
C6H5COCl
C6H5COOR H2O
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9.2 jklk;fud xq.k (Chemical properties) :
NaOH
C6H5COONa
NaHCO3
C6H5COONa + H2O + CO2
Ca-Salt
C2H5OH C6H5COC6H5
C6H5COOC2H5 ∆
H2SO4
COOH
PCl5
C6H5COCl + POCl3 + HCl conc. HNO3/H2SO4
NO2
C6H5COCl + SO2 + HCl SOCl2
COOH
P2O5 C6H5COOH Fuming
(C6H5CO)2O
H2SO4 SO3H
Soda lime
®
C6H6
∆ COOH
(1) N3H, H2SO4
Cl2/FeCl3
C6H5NH2
(2) H2O
Cl
LiAlH4 Neutral FeCl3

C6H5CH2OH buff coloured ppt.
(test)
(i) NH3
C6H5CONH2
(ii) ∆
10.0 vEy O;qRiUu

– –
dkckZsfDlfyd lewg (—COOH) ls (—OH) lewg dk foLFkkiu fdlh ukfHkd Lusgh tSls & Cl , CH3COO ,
– –
C2H5O , NH2 }kjk gksus ij vEy O;qRié izkIr gksrs gSA
O O
– OH R—C—Z
R—C—OH →
+Z
vEy vEy O;qRiUu
R—C— ,d ß,fly lewgÞ gS] Z ,d ukfHkd Lusgh gS] tSls Cl , CH3 COO , C2 H5 O , NH
2
vkfnA
O
Ex. CH3 C ,flfVy lewg
vEy O;qRiéksa dh vfHkyk{kf.kd vfHkfØ;k,sa ukfHkd Lusgh izfrLFkkiu vfHkfØ;k gksrh gS %
Mechanism :
•• 
O O O
••  
CH3–C + Nu → CH3–C + Nu → CH3–C–Nu + Z
Z Z
bl vfHkfØ;k esa Z ,d eqDr gksus okyk lewg gSA nqcZy {kkj vPNs fudklh lewg gSA
fØ;k'khyrk Øe % CH3 COCl > CH3 COOCOCH3 > CH3 COOC2 H5 > CH3 CONH2
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Pre-Medical
10.1 ,lhfVy DyksjkbM (Acetyl Chloride)
—COOH lewg esa ls —OH lewg dk foLFkkiu Cl— ijek.kq ls gksus ij ,flM DyksjkbM izkIr gksrs gSaA
O O
—OH
R—C—OH → R—C—Cl
+Cl
10.1.1 cukus dh lkekU; fof/k;k¡ %

(a) CH3COOH dks PCl3, PCl5 o SOCl2 ds lkFk xeZ djds %
(i) CH3COOH + PCl3 → CH3COCl + H3PO3
(ii) CH3COOH + PCl5 → CH3COCl + POCl3 + HCl
(iii) CH3COOH + SOCl2 → CH3COCl + SO2↑ + HCl↑
(b) vEyks ds yo.kksa dks PCl3, PCl5 ;k SOCl2 ds lkFk xeZ djds %
®
(i) CH3COONa + PCl3 → CH3COCl + Na3PO3
(ii) CH3COONa + PCl5 → CH3COCl + POCl3 + NaCl
(iii) CH3COONa + SOCl2 → CH3COCl + SO2 + NaCl
10.1.2 HkkSfrd xq.k %

(i) ;g ,d rhoz xa/k okyk æo inkFkZ gSA
(ii) DoFkukad 52° C.
(iii) dkcZfud foyk;dks esa ?kqyu'khy ikuh esa /kheh xfr ls foys; gSA
(iv) ue gok esa HCl cuus ds dkj.k /kwe (fumes) mRié djrk gSA
10.1.3 jklk;fud xq.k %
(a) tyvi?kVu % CH3CO Cl + H OH → CH3COOH + HCl
(b) lfØ; H & ;qDr ;kSfxdkas ls fØ;k ¼,flfVyhdj.k½ %

(i) CH3CO Cl + H NH2 → CH3CONH2 + HCl
(ii) CH3CO Cl + H NH–R → CH3CONHR + HCl
1° ,ehu N– ,fYdy ,slhVsekbM

(iii) CH3CO Cl + H NR2 → CH3CONR2 + HCl
2° ,ehu N, N– Mkb,fYdy ,slhVsekbM

(iv) CH3CO Cl + H OR → CH3COOR + HCl
,YdksgkWy
OH OCOCH3
COOH COOH
(v) CH3COCl + + HCl
lsfyflfyd vEy ,fLijhu

(,lhfVy lsfyflfyd vEy)
70

Pre-Medical
O O
(vi) CH3–C–Cl + H – NH – NH2 → CH3–C–NHNH2 + HCl
,lhfVy gkbMªstkbM
O
R
R—C—R + NH2NH2 → C = NNH2
dhVksu R gkbMªstksu
OH OCOCH3
(vii) + CH3COCl → + HCl
Qsfuy ,lhVsV
(c) vip;u %
Pd/BaSO4
®
(i) CH3COCl + H2  → CH3CHO ¼jkstsueqUM vip;u½
(1) LiAlH4
(ii) CH3COCl + 4H →
(2) H2 O
CH3CH2OH + HCl
O O
∆ CH3CO–O–C–CH3 + NaCl
CH3CO Cl + Na O – C – CH3
(d) lksfM;e ,flVsV ds lkFk %
,lhfVd ,ugkbMªkbM
(e) lksfM;e ,FkkWDlkbM ds lkFk% CH3CO Cl + Na OC2H5 → CH3COOC2H5 + NaCl
,fFky ,lhVsV
COCH3
AlCl
(f) ÝhMsy Øk¶V vfHkfØ;k % + CH3COCl 
3
→ + HCl
,lhVksQhuksu
10.2 ,lhfVd ,ugkbMªkbM ¼,FksukWbd ,ugkbMªkbM½ [Acetic Anhydride (Ethanoic Anhydride)]
10.2.1 cukus dh lkekU; fof/k;k¡ (General Method of Preparation) :
(a) futZy lksfM;e ,flVsV dks ,flfVy DyksjkbM ds lkFk xeZ djds ¼iz;ksx'kkyk fof/k½%
O O O
∆
CH3CO Cl + Na O – C – CH3 → CH3 – C – O – C – CH3 + NaCl
(b) ,lhfVd vEy ds futZyhdj.k }kjk %
PO
CH3CO
2CH3COOH 
2 5
→ O + H2O
futZyhdj.k
,lhfVd vEy CH3CO
,lhfVd ,ugkbMªkbM
(i) ;g ,d rh{.k xa/k okyk æo inkFkZ gSA
(ii) ty esa rhozrk ls ?kqyu'khy] bZFkj o ,Ydksgy esa foys;
(iii) DoFkukad 139° C.
71
®

Pre-Medical
H—OH
(a) ty vi?kVu % CH3CO—O—COCH3 → CH3COOH + CH3COOH
ty vi?kVu dk Øe: {kkjh; > vEyh; > mnklhu

+ –
Na OH
CH3CO–O–COCH3 → CH3COONa + CH3COOH
lksfM;e ,flVsV ,lhfVd vEy

(b) lfØ; H- ;qDr ;kSfxdks ls fØ;k ¼,flfVyhdj.k½ % &
(i) CH3—CO—OCOCH3 + H NH2 → CH3CONH2 + CH3COOH
(ii) CH3CO—OCOCH3 + H NHR → CH3CONHR + CH3COOH
®
(iii) CH3CO—O—COCH3 + H NR2 → CH3CONR2 + CH3COOH
(iv) CH3CO—O—COCH3 + H OR → CH3COOR + CH3COOH

OH OCOCH3
COOH COOH
(v) CH3CO—O—COCH3 + + CH3COOH
¼lsfyflfyd vEy½ (,fLijhu)
(c) vip;u % bZFkj esa LiAlH4 ds lkFk ,fFky ,YdksgkWy nsrk gSA
LiAlH4
CH3CO —O —COCH3  → 2CH3CH2OH + H2O
(d) PCl5 o SOCl2 ls fØ;k %
CH3CO—O—COCH3 → 2CH3COCl + POCl 3
QkWLQksjl vkWDlhDyksjkbM
Cl—PCl3—Cl
CH3CO—O—COCH3 → 2CH3COCl +SO2

Cl—SO—Cl
10.2.4 mi;ksx %
(i) ,d ,lhfVyhdkjd ds :i esa
(ii) lsY;qyksl ,lhVsV] ,fLijhu] fQusflVhu] ,lhVkekbM o ,lhVksfQuksu vkfn ds fuekZ.k esa
(iii) gkbMªkWfDly o ,ehuksa lewg ds ijh{k.k o ekiu esa
10.3 ,LVj (Esters)
(a) fV'kSUdks vfHkfØ;k % ,lhVsfYMgkbM dh ,Y;wehfu;e bFkksDlkbM ls fØ;k djkds ¼vk/kqfud dSfutkjks vfHkfØ;k½
(C H O) Al
2CH3CHO 
2 5 3
→ CH3COOC2H5
,sfFky ,lhVsV
O O
Conc.H2 SO4
(b) ,LVjhdj.k : CH3—C—OH + HO—C2H5  CH3—C—OC2H5 + H2O

∆
,fFky ,flVsV
72

Pre-Medical
BEGINNER'S BOX-6
1. ,sYdsuksbd vEy fdlds ty&vi?kVu ls curs gSa %&
(1) VªkbgSyks,sYdsuksa ds (2) 1,1,1– VªkbgSyks,sYdsuksa ds
(3) dhVksu (4) xzhU;kj vfHkdeZd ds
2. vEyksa ds DoFkukad leko;oh ,LVj ls vf/kd gksrs gSa D;ksafd%&
(1) vEy gkbMªkstu ca/k }kjk f}yd cukrs gSa
(2) vEy Hkki esa ok"i'khy gksrs gSa
(3) ,LVj vok"i'khy gksrs gSa
(4) vEy tyh; foy;u esa vk;fur gksdj izksVkWu nsrs gSa
3. fuEufyf[kr esa ls dkSulk ;kSfxd vUrjv.kqd H–ca/k cuk ldrk gS%&
(1) ,fFky ,slhVsV (2) esfFky QkWesZV
®
(3) ,slhV,sekbM (4) ,slhfVd ,sugkbMªkbM
4. ,fFky ,slhVsV dh lksfM;e ,FkkWDlkbM ls vfHkfØ;k gksus ij ,slhVks,slhfVd ,LVj curk gSA ;g vfHkfØ;k fdl
oSKkfud ds uke ls tkuh tkrh gS %&
(1) Dystu (2) dSfutkjksa
(3) DyhesUlu (4) ,sVkMZ

(i) Qyks tSlh xa/k okyk æo inkFkZ gSA
(ii) DoFkukad 77° C.
(iii) ty esa vkaf'kd foys; fdUrq dkcZfud foyk;dksa esa iw.kZ foys; gSA
(a) tyvi?kVu % vEyh; ek/;e esa fØ;k mRØe.kh; gksrh gS] tcfd {kkjh; ek/;e esa fØ;k vuqRØe.kh; gksrh gSA
H+

CH3COOC2H5 + HOH   CH3COOH + C2H5OH
CH3COOC2H5 + NaOH →  CH3COONa + C2H5OH
∆
(b) veksuhvi?kVu: CH3CO OC2H5 + H NH2 → CH3CONH2 + C2H5OH
,lhVsekbM ,sFksuksy
(c) NH2NH2 ,oa NH2OH ls fØ;k %
∆
CH3CO OC2H5 + H NHNH2 → CH3CONHNH2 + C2H5OH
gkbMªsthu ,lhfVy gkbMªstkbM

∆
CH3CO OC2H5 + H NHOH → CH3CONHOH + C2H5OH
gkbMªksfDly ,ehu ,flfVy gkbMªkWDlsfed vEy

LiAlH
(d) vip;u : CH3COOC2H5 
4
→ CH3CH2OH + C2H5OH
(e) Dystu la?kuu %

NaOC H
CH3CO OC2H5 + H CH2COOC2H5 → CH3COCH2COOC2H5 + C2H5OH
2 5
73
®

Pre-Medical
10.4 ,lhVsekbM (Acetamide)
(a) vEy O;qRiéks ds vehuksa vi?kVu ls %
CH3CO Cl + H NH2 → CH3CONH2 + HCl
CH3CO — O — COCH3 + H NH2 → CH3CONH2 + CH3COOH

∆
CH3CO OC2H5 + H NH2 → CH3CONH2 + C2H5OH
(b) ,fYdy lk;ukbMksa ds ty vi?kVu ls % vkaf'kd ty vi?kVu ds }kjk

R—C ≡ N + H2O → R – C – NH2
O
CH3—C ≡ N + H2O → CH3 – C – NH2
®
O

(i) ,lhVsekbM+ ,d lQsn fØLVyh; Bksl inkFkZ gSA
(ii) 'kq) ,lhVsekbM+ xa/kghu gksrk gSA
(iii) v'kq) ,lhVsekbM+ esa pwgs tSlh xa/k vkrh gSA
(iv) fuEurj ,ekbM H– cU/k ds dkj.k ty esa foys; gksrs gSA
(v) buds mPp xyukad o DoFkukad Hkh vUrj vk.kfod H - cU/k ds dkj.k gh gksrs gSA
O HNH–C=O HNH–C=O
H2N—C—R R R
(a)ty vi?kVu % vEyh; ek/;e esa ,ekbM dk ty vi?kVu rhozrk ls gksrk gSA {kkjh; ek/;e ,ekbM ds
ty vi?kVu ds fy, mPp rki dh vko';drk gksrh gSA
+ +
H
R—C—NH2 + H2O → R—COOH + N H4
O
∆
CH3—C—NH2 + NaOH → CH3COONa + NH3 ↑
O
(b) izkFkfed ,ehu esa vip;u % ,ehu esa C– la[;k leku jgrh gSA
LiAlH or
CH3CONH2 
4
→ CH3CH2NH2 + H2O
Na C2 H5 OH
1° ,ehu
(c) PCl5, SOCl2 ;k P2O5 ds lkFk futZyhdj.k :
PCl −2HCl
CH3CONH2 
5
→ CH3CCl2NH2  → CH3CN + 2HCl
esfFky lk;ukbM
∆
CH3CONH2 + P2O5 → CH3CN + H2O
esfFky lk;ukbM+
74

Pre-Medical
(d) ukbVªl vEy ls fØ;k %
HNO
CH3—CO—N H2 
2
→ CH3COOH + N2+ H2 O
HO — N = O
(e) gkWQeku&czkse,ekbM+ vfHkfØ;k % ,ekbM] czksehu rFkk (NaOH ;k KOHds lkFk) izkFkfed ,ehu cukrs gS
ftuesa ,ekbM ls ,d C– ijek.kq de gksrk gSA
CH3CONH2 + Br2 + KOH(aq.) → CH3NH2 + KBr + K2CO3 + H2O
or (KOBr)
fØ;kfof/k :
O –
O O
– Br–Br
KOH
CH3—C—N—H CH3—C—N—H CH3—C—N—Br
®
H H
–
KOH
O O
–
Rearrangement –Br
CH3—N=C=O CH3—C—N CH3—C—N—Br
2KOH (Acetylnitrene)
CH3—NH2+ K2CO3
ANSWER'S KEY
Que. 1 2 3
BEGINNER'S BOX-1
Ans. 3 4 2
Que. 1 2
BEGINNER'S BOX-2
Ans. 1 2
Que. 1 2 3
BEGINNER'S BOX-3
Ans. 3 2 3
Que. 1 2 3
BEGINNER'S BOX-4
Ans. 2 4 1
Que. 1 2 3
BEGINNER'S BOX-5
Ans. 4 2 3
Que. 1 2 3 4
BEGINNER'S BOX-6
Ans. 2 1 3 1
75

Oxygen Contaning Compound

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vkWDlhtu ;qDr ;kSfxd (OXYGEN CONTAINING COMPOUND)

1.0 gkbMªkWDlh O;qRiUu (HYDROXY DERIVATIVES)

,fyQsfVd gkbMªkWDlh O;qRiUu ,jksesfVd gkbMªkWDlh O;qRiUu

(iii) VªkbZgkbfMªd [rhu –OH] → CH2 – CH – CH2

(iv) ikWyhgkbfMªd [n –OH] → CH2 – CH – CH – CH – CH – CH2

(b) dkcZu dh izÑfr ds vk/kkj ij oxhZdj.k %

(ii) f}rh;d ;k 2° – ,YdksgkWy → (CH3)2CH – OH

(iii) r‘rh;d ;k 3° – ,YdksgkWy → (CH3)3C – OH

2.0 eksuksgkbfMªd ,YdksgkWy (MONOHYDRIC ALCOHOL)

2.1 cukus dh lkekU; fof/k;k¡ (General Methods of Preparation)

(i) ,Ydsu ls ¼vkWDlhdj.k }kjk½ %

(iv) dkcksZfuy ;kSfxdksa ls ¼vip;u }kjk½ %

GOLDEN KEY POINTS

vipk;d inkFkZ gks ldrs gSaA

Note : ,ekbM+ vipf;r gksdj ,ehu cukrs gS ,YdksgkWy ughaA

e/;orhZ dkcZ/kuk;u gksrk gS vr% iqufoZU;kl laHko gSA

CH3CH2CH2CH2OH < CH3CH2CH–OH < CH3–C–OH

CH3CH2CH2 < CH3–CH–CH2 < CH2–CH–CH2

CH3CH2CH2CH2OH > CH3CH2CH–OH > CH3–C–OH

CH3CH2CH2 < CH3–CH–CH2 < CH2–CH–CH2

¼OH dh la[;k c<us ij H ca/ku c<+rk gSA½

Illustration 3. ,YdksgkWyksa dk DoFkukad laxr dkcksZfDlfyd vEy ls de gksrk gSA D;ksa\

2.3 jklk;fud xq.k (Chemical Properties)

eksuksgkbfMªd ,YdksgkWy fuEu vfHkfØ;k n'kkZrs gSaA

CH3—OH > CH3CH2—OH > (CH3)2CH—OH > (CH3)3C—OH

(i) vEyh; izÑfr %

lsfyflfyd vEy ,lhVkWDlh csUtkWbd vEy

futZyhdkjd ds :i esa 'kq"d HCl dk Hkh mi;ksx fd;k tk ldrk gSA

Ex. CH3–C– OH + H– OC2H5  ∆ →

GOLDEN KEY POINTS

H – C – OH > CH3 – C – OH > CH3 – CH – C – OH > CH3 – C – C – OH

(vi) CH≡CH ds lkFk vfHkfØ;k %

vEyksa dh fØ;k'khyrk dk Øe HI > HBr > HCl

(ii) QkLQksjl gSykbM ds lkFk vfHkfØ;k %

(C) vfHkfØ;k ftuesa iw.kZ ,YdksgkWy v.kq Hkkx ysrk gS %

futZyhdj.k dh lqxerk dk Øe % 3° ROH > 2° ROH > 1° ROH

¼p- ,YdksgkWy½ ¼,flVSfYMgkbM½

¼s- ,YdksgkWy½ ¼,lhVksu½

¼p- ,YdksgkWy½ ¼leku dkcZu vEy½

R—CH2—I R2CH—I R3C—I

AgNO2 AgNO2 AgNO2

RCH2—NO2 R2CH—NO2 R3C—NO2

R – C – NO2 R2C – NO2 No reaction

Nitrolic acid (uhyk) Pseudonitrol (uhyk) jaxghu

Sodium nitrolate (yky) No reaction (uhyk)

(v) CH3 – OH vkSj C2H5OH es foHksnu %

DoFkukad 65°C 78°C

I2 + NaOH vo{ksi ugha CHI3 dk ihyk vo{ksi

Cu/300°C QkesZfyu dh xa/k [HCHO] xa/k ugha

,YdksgkWyksa ds fo"k; esa egRoiw.kZ rF; %

CHO CHO CHO

4.0 ,sjkseSfVd gkbMªkWDlh O;qRiUu (AROMATIC HYDROXY DERIVATIVES)

QhukWy o-fØlkWy lSfyflfyd vEy

dsVsdkWy fjlkWflZukWy fDoukWy

(3) QhukWfyd vEy dk vklou lksMk ykbe ds lkFk djus ij ¼fodkcksZfDlyhdj.k½ %

(6) Dyksjks csUthu ls %

(1) Aq. NaOH, ∆ & Pr