ALLEN® Carbonyl Compounds 1

CARBONYL COMPOUNDS 5. fuEufyf[kr esa ls dkSu lh vfHkfØ;k

,slhVSfYMgkbM ugha cuk,xh\
1. fuEufyf[kr esa ls dkSulk vfHkdeZd vfHkfØ;k
?
CH 3CH 2 CH 3 ¾¾ ® CH 3 CH 2 CHO (1) CH3CH2OH ¾¾¾
Cu
573K
®
ds fy, iz;ksx fd;k tkrk gS\ (i) DIBAL - H
(1) eSaxuht ,slhVsV (2) CH3CN ¾¾¾¾¾
(ii) H2 O
®
(2) mPp rki o nkc ij dkWij
(3) ekWfyCMsue vkWDlkbM (3) CH2=CH2 + O2 ¾¾¾¾¾
Pd(II)/Cu(II)
H2 O
®
(4) iksVfS 'k;e ijeSaxusV CrO3 - H 2 SO 4
2. mRikn A rFkk B dks igpkfu,: (4) CH3CH2OH ¾¾¾¾¾ ®
CH3 6. fuEufyf[kr vfHkfØ;k dk eq[; mRikn gS %
dil. KMnO 4 CrO3
273 K
A B (1) H3O+, D
CH3 CH3 (2) SOCl2
(1) A : B: CH3CH2CN ?
OH (3) Pd/BaSO4,H 2
OH O
CH3 CH3 (1) CH3CH2CH3 (2) CH3CH2CH2OH
(2) A : OH B: OH (3) (CH3CH2CO)2O (4) CH3CH2CHO
OH O
O A (ty lay;u)
Hydrolysis B
7. (C4H8Cl2) 373K (C4H8O)
(3) A : OHC—CH2CH2CH 2—C—CH 3
O B gkbMªksfDly ,sehu ls vfHkfØ;k djrk gS ijUrq
B : HOOC—CH2CH2CH2—C—CH3 VkWysu ijh{k.k ugha nsrk gSA A rFkk B dks
CH3 CH3 igpkfu,A
(4) A : B: (1) 1,1-MkbDyksjksC;wVsu rFkk 2-C;wVu s kWu
OH O
(2) 2,2-MkbDyksjksC;wVsu rFkk C;wVsusy
3. fuEu esa ls dkSuls dkcksZfuy ;kSfxd dks HgSO4
(3) 1,1- MkbDyksjksC;wVsu rFkk C;wVsusy
rFkk H2SO4 dh mifLFkfr esa ,sYdkbu ij ty ds (4) 2,2-MkbDyksjksC;wVsu rFkk 2-C;wVus -vkWu
8. 2,4-DNP ijh{k.k ftldks ifgpkuus ds fy, fd;k
;ksx }kjk ugha cuk;k tk ldrk gS? tkrk gS] og gS :
(1) ,sehu (2) ,sfYMgkbM
O O (3) bZFkj (4) gSykstu
(1) CH3–C–H (2) C–CH3
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9. nh x;h jklk;fud vfHkfØ;k esa A dks ifgpkfu,A

O O CH2CH2CHO NaOH
(3) CH 3–CH 2–C–H (4) CH3–C–CH2CH3 C 2 H 5 OH, H 2 O A(eq[; mRikn)
CH2CH2CHO D
4. fuEufyf[kr esa ls dkSu&lk vfHkdeZd mijksDr CHO
vfHkfØ;k esa mRikn esa fuekZ.k ds fy, mi;qDr gS\ (1)
(1) NaBH4 CH2CH2COOH
! Å
(2)
(2) NH2–NH2/ C2 H5 ONa CH2CH2CH2OH
(3) Ni/H2 O

(4) yky P + Cl2 C–H

(3)
O
(4)
O

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2 Carbonyl Compounds ALLEN®
10. uhps nh x;h vfHkfØ;k esa A dks ifgpkfu,A O O
Ethylene Glycol
13. A
CHO OC2H 5 H+ (eq[; mRikn)
¾¾¾¾¾¾¾¾
®
(i) HCHO, NaOH
(ii) CH3 CH 2 Br, NaH, DMF A mijksDr vfHkfØ;k esa mRikn "A" gS :
CH3O (iii) HI, D
OH
O O O O
OH O O
C – OCH2CH3 (1) (2)
(1) OC2H5 OC2H 5
HO
CH2OH O

(2) OC2H 5 O
O
CH3O (3) (4) O
CH 2I OH
OH
(3) O
HO dil.NaOH +

CH2OH 14. ¾¾¾¾ ®"X" ¾¾¾¾

H , Heat
® "Y"
2
(4)
HO mijksä vfHkfØ;k ds mRikn 'X' rFkk 'Y' Øe'k: gSa
OH
O
11. ¾¾¾¾¾®(1) Zn / HCl
(2) Cr2O3 , 773K
O 10 -20 atm (1) ,
O
mijksDr vfHkfØ;k dk eq[; mRikn gS : O O

(1) (2) ,
OH
O O

(2) CH2CH2CH3 (3) ,

OH
O O

(3) CH3 (4) OH ,

CH3
15. ,sYMhgkbMksa ds Vkysu ijh{k.k esa flYoj niZ.k izkIr
djus ds fy, bysDVªkWuksa dh lEiw.kZ la[;k tks
(4) COCH2CH3 Vkysu vfHkdeZd (lw=k [Ag(NH3)2]+) dks
LFkkukarfjr gksrh gS izfr ,YMhgkbM xqzi] og
gS_______A (fudVre iw.kk±d esa)
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O OH
O
i) DIBAL-H, VkWyqbu,–78°C "P"
16.
CHO O
12. ii) H3O+
(eq[; mRikn) OH
OH
mijksDr vfHkfØ;k esa mRikn "P" gS : (I) (II) (III) (IV)
OH mijksDr ;kSfxdksa eas ls dkSu lk@ls VkWysu
COOH CHO vfHkdeZd ls fØ;k djds flYoj niZ.k ugha
(1) (2)
cukrk@rs gS?
O
(1) dsoy (I), (III) rFkk (IV)
O–C–H
(2) dsoy (IV)
CHO
(3) (4) (3) dsoy (II)
(4) dsoy (III) rFkk (IV)

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 ALLEN® Carbonyl Compounds 3
17. fuEufyf[kr vfHkfØ;k esa eq[; mRikn (P) gS% 20. ,d dkcZfud ;kSfxd 'A' C4H8, KMnO4/H+ ls
O
CHO vfHkfØ;k djus ij ,d ;kSfxd 'B' C3H6O nsrk gSA
(i) KOH (alc.)
¾¾¾¾®
(ii) H , D
+ P
O (eq[; mRIkkn) ;kSfxd 'A' vkstksuh vi?kVu ls Hkh ;kSfxd 'B' nsrk
O gSA ;kSfxd 'A' gS :
OHC O
(1) 2–esfFkyizksihu
(1) (2)
O (2) 1–esfFkylkbDyksizksisu
O
(3) C;wV–2– bZu
CHO
(3) (4) (4) lkbDyksC;wVsu
O O 21. csUtksukbVªkby dh ,d rqY;kad CH3MgBr ls
O (i) C2H5MgBr, 'kq"d bZFkj
(ii) H2O, HCl vfHkfØ;k] rRi'pkr ty vi?kVu] ,d ihys jax
18.
P
(eq[; mRikn) dk nzo "P" nsrh gSA ;kSfxd "P" tks ikWftfVo
mijksDr vfHkfØ;k ij fopkj dj crkb, fd eq[; ijh{k.k nsrk gS] og gS %
mRikn 'P' gS :
OH (1) vk;MksQkeZ ijh{k.k (2) f'kQ ijh{k.k
(1)
(3) fuugkbfMªu ijh{k.k (4) VkWysu ijh{k.k
OH t – +
22. Br EtOH excess
CHO ¾¾¾®
dry HCl gas
"A" BuO K
¾¾¾® "B"
(2) (major (major
product) product)
OH
[tgk¡ Et Þ –C2H5 tBu Þ (CH3)3C–]
(3) mijksDr vfHkfØ;k Øe ij fopkj djs]a fufeZr
Cl mRikn "A" rFkk mRikn "B" Øe'k% gSa :
OH
OEt H2C OEt
(4) (1) Br
Cl
,
OEt OEt
O
OtBu
CH3CHO (i) I2/NaOH, Nkuuk (2) EtO CHO EtO
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19. NaOH
'P' (ii) Nkuk gqvk nzo + HCl 'X' ,
OH
(eq[;
OEt H2C OEt
mRikn) (3) EtO
nh x;h vfHkfØ;k ij fopkj dhft,A bldk ,
OEt OEt
mRikn 'X' gS : OEt OEt
O O (4) Br t
BuO
OH O ,
OEt OEt
(1) (2)

OH O O
(3) (4)
CHO OH

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4 Carbonyl Compounds ALLEN®
23. fuEufyf[kr ;kSfxdksa esa ls dkSu lk ;kSfxd 26. lwph-I dk feyku lwph-II ls djsaA
2,4-MkbZukbVªksQfs uy gkbMªSthu ds lkFk mipkfjr
djkus ij ukjaxh vo{ksi nsrk gS ? lwph-I lwph-II
OH (jklk;fud vfHkfØ;k) (vfHkdeZd )
(1) (a) CH3COOCH2CH3 ® CH3CH2OH (i) CH3MgBr / H3O
+

OCH2CH3 (1.equivalent)
(b) CH3COOCH3 ® CH3CHO (ii) H2SO4 / H2O
O
O
(c) CH3C º N ® CH3CHO (iii) DIBAL-H/H2O

(2) OCH2CH3 O

(d) CH3C º N ® CH3 CH3 (iv) SnCl2, HCl/H2O

O lgh feyku gS &

C– OH (1) a-ii, b-iv, c-iii, d-i (2) a-iv, b-ii, c-iii, d-i
(3) a-ii, b-iii, c-iv, d-i (4) a-iii, b-ii, c-i, d-iv
(3)
O OH
OH "X" CN
27. H HCN,H O
O 2 H
¯
"Y" LiAlH4
(4) CH3 +
(eq[; mRikn) H3O

24. (i) DIBAL - H

R – CN ¾¾¾¾¾¾¾ nh xbZ vfHkfØ;k ij fopkj djsaA 'X' ,oa 'Y' dks
(ii) H O
® R–Y
2
mijksDr vfHkfØ;k ij fopkj dj "Y" dks igpkusaA
igpkfu, %
(1) –CH2NH2 (2) –CONH2 OH
(3) –CHO (4) –COOH NH2
(1) X – NaOH Y – H
25. fuEufyf[kr vfHkfØ;k Øe es fojfpr eq[; mRikn
A rFkk B gS : OH
O
(2) X – HNO3 Y –
CH3 Br2 H NH2
A+B
KOH OH
O (3) X – NaOH Y –
H NH2
(1) A = C , B=CHBr3
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OK OH
(2) NH2
(4) X – HNO3 Y –
O O H
A= C–CH2–Br ,B= C–CH2–OH
28. ,d Dyksjks ;kSfxd "A".
Br Br
O (i) vkstksuh vi?kVu rnqiajkr ty vi?kVu ij

(3) A= C–CBr3 , B= CHO ,sfYMgkbM fufeZr djrk gSA

(ii) iw.kZ :i ls okf"ir djus ij 1.53 g A STP ij
Br HO 448 mL ok"i nsrk gSA
O O
(4) A= C–CH3 , B= C–CH3 ;kSfxd A ds ,d v.kq esa dkcZu ijek.kqvksa dh
Br HO la[;k gS _______

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 ALLEN® Carbonyl Compounds 5
29. fuEufyf[kr vfHkfØ;kvksa ds Øe esa vfUre mRikn 32. vfHkfØ;kvksa ds fuEu Øe esa
+
D gS: ® A ¾¾¾¾
C3H6 ¾¾¾¾ ruq KOH ® B + C
H /H2 O KIO

OH
;kSfxd B ,oa C Øe'k% gSa]
Br CH H2/Pd–C CrO3
CH –CºC–H+NaNH A 3
B C D
3 2 (1) CI3COOK, HCOOH (2) CI3COOK, CH3I
O (3) CH3I, HCOOK (4) CHI3, CH3COOK
(1) H3C–CH2–CH2–CH2–CH2–C–H

(2) CH3–CH=CH–CH2–CH2–CH2–COOH 33. uhps nks dFku fn, x;s gSa %

(3) H3C–CH=CH–CH(OH)–CH2–CH2–CH3
dFku I : ,d ,sfYMgkbM ;k ,d dhVksu ij
O
lksfM;e gkbMªkstu lYQkbV ds ukfHkdLusgh
(4) CH3–CH2–CH2–CH 2–CH2–C–CH3
la;kstu esa izkVs kWu LFkkukarj.k ds dkj.k ,d LFkk;h
30. fuEufyf[kr vfHkfØ;k esa iz;qDr izkjfEHkd ;kSfxd
vk;u fufeZr gksrk gSA
P dh lajpuk gS:
dFku II : ,d ,sfYMgkbM ;k ,d dhVksu ij
OH
1. NaOCl
P gkbMªkstu lk;ukbM ds ukfHkdLusgh la;kstu]
2. H3O+
O
vafre mRikn ds :i esa ,sehu nsrk gSA
H
(1) (2) mi;qZDr dFkuksa ds lanHkZ esa uhps fn, x, fodYiksa
O O esa ls lgh mÙkj pqusa :
O (1) nksuks dFku I ,oa dFku II lgh gSaA
O (2) dFku I lgh gS ,oa dFku II xyr gSA
(3) (4)
(3) dFku I xyr gS ,oa dFku II lgh gSA
31. uhps nh x;h vfHkfØ;k ds fy, % (4) nksuksa dFku I ,oa dFku II xyr gS
CHO
1. NaOH, D
mRikn
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2. H3O+
CH2OH

;kSfxd ftldk vfHkfØ;k esa mRikn ds :i esa

fojpu ugha gksrk gS] og gS %
(1) nks] fØ;kRed xzqi ,sYdksgkWy rFkk ,sflM lfgr

;kSfxd
(2) eksuksdkcksZfDlfyd vEy

(3) MkbdkcksZfDlfyd vEy

(4) MkbvkWy

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6 Carbonyl Compounds ALLEN®
SOLUTION 5. Official Ans. by NTA (4)
1. Official Ans. by NTA (3) O
CrO3×H2SO4
Sol. CH3–CH2–OH CH3–C–OH
Sol. CH3–CH2–CH3 ¾¾¾®
MO O
CH3–CH2–CH=O2 3
Strong oxidising
agent (Carboxylic
acid is formed
The reagent used will be MO2O3 by complete
oxidation )
2. Official Ans. by NTA (2)
HO 6. Official Ans. by NTA (4)
dil.KMnO4 O O
Sol. (i) H3O /D
+
(2) SOCl
273 K (A) Sol. Et-CºN Et–C–OH Et–C–Cl
2

OH O (3) Pd/BaSO 4
H2
CrO3 Et–C–H Resonmund's
reduction
O
Final product of reaction is propanaldehyde.
7. Official Ans. by NTA (4)
OH
Sol.
3. Official Ans. by NTA (3)
Cl OH O
Sol. Reaction of HgSO4/dil.H2SO4 with alkyne gives Hydrolysis
373 K –H2O
addition of water as per markonikoff's rule. Cl OH
O (C4 H8Cl2) (C4H8O)
HgSO
(1) HCºCH H SO 4 CH2–CH CH3–CH (A) (B)
2 4
OH
8. Official Ans. by NTA (2)
HgSO
(2) CºCH H SO 4 Sol. 2,4-DNP test is useful for the identification of
2 4

O carbonyl compounds.
C=CH2 C–CH3
9. Official Ans. by NTA (3)
OH
O Sol.
HgSO4
(3) CH3–CºCH H SO CH3–C=CH2 CH3–C–CH3 O
2 4
OH CH2 CH C H
Hence CH3–CH2–CHO cannot be form. H OH—
HgSO CH2 CH2 C H
(4) CH3–CºC–CH3 H SO 4 CH3–C=CH–CH3 O
2 4
O
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OH 2
CHO 3 1
H
H
CH3–C–CH2–CH3 7 H
OH 4 6
O 5
O
4. Official Ans. by NTA (2)
CHO
C2H5OH/D
(i) NH2–NH 2 –H2O
Sol. (ii) EtO– Na+/D
O

To reduce the carbonyl groups into alkane wolf

– kischner reduction is used, without affecting
the double bond.

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 ALLEN® Carbonyl Compounds 7
10. Official Ans. by NTA (3) 14. Official Ans. by NTA (3)
O O O
Sol.
Sol. H OH
O –H2O
C–H

NaOH H 2O
+ H–C–H Cannizaro
H – C – ONa
O O
OCH3 O OH
+ O
D
H3CO CH2 – OH
(X)
(Y)
15. Official Ans. by NTA (2)
CH3–CH2–Br
Sol. AgNO3 + NaOH ® AgOH + NaNO3
H 3C – O CH2 – O – CH2 – CH3 2AgOH ® Ag2O + H2O
I–H I–H 1
Ag2O + 4NH3 + H2O ® 2Ag(NH3)2+ + 2OH
.
HI D O .
–e– OH
HO O
R–C–H +
CH2 – I R H R H
O Ag+ Ag

+ CH3 – I + CH3 – CH2 – OH

D HI
OH O OH
e–
CH3–CH2–I . HO .
Ag+ Ag R OH R OH
11. Official Ans. by NTA (1)

Sol. Zn – Hg / HCl R – C – OH R–C–O

O O
O Cr2O3, 773 K
10–20 atm Total 2e– transfer to Tollen's reagent
16. Official Ans. by NTA (3)
Sol. Aldehydes give Åve Tollen's Test (Silver mirror
test)
Tollen's test
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12. Official Ans. by NTA (2) (I) Positive

CHO
O H
O OH O
OH C=O Tauto

(i) DIBAL-H (II) Negative

Sol. (ii) H 3OÅ Ketone
O
DIBAL can not reduce double bond (III) Tauto Positive
OH H
It can reduce cyclic ester.
13. Official Ans. by NTA (2) O [Ag(NH3)2]+OH1 O O1
(IV) H
–H2O
OH OH O1
O O O
OH O OO C2H5
Hemiacetal
Sol. H
+
OC2H5 O
Positive

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8 Carbonyl Compounds ALLEN®
17. Official Ans. by NTA (2) 20. Official Ans. by NTA (1)
H3C CH3
Sol. CH=O C=O KMnO4/HÅ H3C
CH2–CH2 (i) KOH (alc.) O O
O
+
(ii)H . D O
Sol.H3C CH2 Ozonolysis
H3 C
Intramolecular Aldol condenstion (P)
2-Methylpropene C3H6O
(Major Product)

18 Official Ans. by NTA (3) 21. Official Ans. by NTA (1)

Sol. Å Sol.
O O Mg
CH3–CH2MgBr CH3
1,2-Addition CºN C = NMgBr
CH3MgBr

Benzonitrile H3O+
Hů HOH | HCl
Å
O–H
OH C – CH3 + NH3

Å O
It gives positive Iodoform test
Cl–
22. Official Ans. by NTA (1)
OH Sol.
EtOH (excess)
Br – CH2 – CH = O
Dry HCl gas
Cl
OEt
19. Official Ans. by NTA (4) Br – CH2 – CH (Acetal)
(A)
Sol. OEt
E2 Tertiary
mechanism butoxide

OEt
O O CH2 = C
O CH3–C–H O O (B)
OH OEt
H CH
CH3
Enolate RDS
23. Official Ans. by NTA (4) node06\B0BA-BB\Kota\JEE MAIN\Jee Main-2021_Subject Topic PDF With Solution\Chemistry\Hindi\Carbonyl Compounds

O
H–O–H
C
O
O Å O OH Sol. CH3
C–ONa (i) I2, NaOH
+ CHI3 CH3
(Yellow ppt) Iodoform Test Explanation Þ 2-4-D.N.P test is used for
(Filtrate)
carbonyl compound (aldehyde & ketone)
HCl
24. Official Ans. by NTA (3)
O O
Sol.
OH

Here Y is Aldehyde

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 ALLEN® Carbonyl Compounds 9
25. Official Ans. by NTA (1) 29. Official Ans. by NTA (4)
— +
Sol. C–CH3
Br2 Sol. CH3–Cº CH + NaNH2 ® CH3–CºC Na + NH3
A+B (A)
+KOH
O OH

O Br CH3

(1)
OH
C , B=CHBr3
OK CH3–CºC–CH2–CH2–CH–CH3
(B)
26. Official Ans. by NTA (3) H2/Pd–C
Sol.
CH3–CH2–CH2–CH2–CH2–CH–CH3
H3O+
CH3–C–O–CH2CH3 CH3CO2H+CH3CH2OH CrO3 (C)
OH
O
CH3–CH2–CH2–CH2–CH2–C–CH3 (D)

CH3–C–O–CH3 DIBALH/H2O CH3CHO O

–78ºC
O
30. Official Ans. by NTA (1)
SnCl2+HCl Sol.
CH3–CN CH3CH=O
/H2O
O O
O NaOCl
CH3MgBr (1eq) H3O+ OH + CHCl3
CH3–CºN
/H3O+ [P]
chloroform
Methyl ketone
27. Official Ans. by NTA (3)
NaOCl is used in haloform reaction as reagent.
Sol.
31. Official Ans. by NTA (3)
O OH
NaOH(x) Sol.
H HCN/H2O H CºN CHO CH2–OH COO–Na+
X Þ NaOH
LiAlH4 NaOH
+
OH OH D
NH2 NH2
YÞ
H H CH2–OH CH2–OH CH2–OH
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g(major product)
28. Official Ans. by NTA (3) H3O+

Sol. 448 ml of A Þ 1.53 gm A

CH2–OH COOH
1.53
22400 ml of A Þ × 22400 gm A = 7650
445
+
H3CHC–CH–Cl O3
CH3–CH=O
It has 3 carbon atoms Zn /H2O Aldehyde
CH2OH CH2–OH
& mm is 36 + 5 + 35.5 = 76.5

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10 Carbonyl Compounds ALLEN®
32. Official Ans. by NTA (4)
Sol.

33. Official Ans. by NTA (2)

Sol. Statement I : Correct

Statement II :

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