Carbonyl

Page # 24 CARBONYL COMPOUNDSE
Exercise - I (Only one option is correct)


3. (x) OH
  -hydroxy ketone
O H 2O
1. OH
 (P) major product (x) can’t be
H 2O
O O
Stucture of (P) is
(A)
OH
OH O
(A) (B)
O
O O
(B) O
OH
O O
(C) (D)
(C)
O O
OH (D)
2. (x) dil
.NaOH

 (x) is H—C—H
C — CH3
O
O
O 4. O dil
.KOH

(A) O
(P) major product
O O
OH
(B)
OH
O (A) (B) C — CH3
O
O
(C)
O
OH
O
H3C
(C) (D) None
OHC
(D)
O
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CARBONYL COMPOUNDS Page # 25
O
dil.KOH
5.   (x)
O O 
9. (x) + (y) dil
.NaOH


major product structure of (x) is 
O O (x) and (y) are

O O
OH CHO
(A) (B)
(A) and
HO O O
COH
CHO
(C) (D) (B) and
O O
CH3
6. Aldol addition can be
(C) and
(A) Acid catalysed (B) Base catalysed
(C)Acid promoted (D) A and B both (D) None
O
O
dil. KOH H Ag

7. (x)  Structure of (x) is 10. 2 O
. NH 4 OH
 (p)
HO
Product (P) is
O
O
O
(A) (B) (A) OH
OH
OH
(C) (D) (B)
OH
HO
O
O (C) OH
8. + O
Dil
.KOH


HO
O
Total number of aldol condensation products
are (excluding stereoisomer)
(A)2 (B)3 (D) H
(C)4 (D)5 O
O O
11.
OH (x) O 16. (
i ) Dil NaOH
  Product
 ( ii ) 
Reagent (x) is Degree of unsaturation in product is?

(A) PCC (B) CrO3,H2SO4,H2O (A) 2 (B) 3
(C) Ag2O,NH4OH (D)All (C) 4 (D) 5
COOH O
CHO
— CH3
12. (CHOH)4 (CHOH)4

HO

17. heat C.Compound (C) is:
CH2OH (Re tro )
CH2OH
OH
Reagent responsible for given conversion will
be
O
(A)Ag2O,NH4OH (B)Br2,H2O
(C) Cu+2 (D)All O
C — CH3
13. Conc . NaOH
HCHO   (x) + (y)
(A) (B)
(i) Oxidation number of carbon changes from
(A) O to +1 and 0 to –2 O
(B) 0 to +1 and 0 to –1
O O
(C) 0 to +2 and 0 to –2
(D) None
(ii) Given reactin is an example of (C) (D)
(A) oxidation (B)Reductopn
(C)both (D)None
14. Compound which gives cannizaro reaction? 18. This is an example of an intramolecular aldol
(A)CD3CHO (B) C6H5CHO O
O
(C)CH3COCH3 (D)
reaction: H
2SO 4
 (A),
H 2O
O
15. Compound which gives intramolecular aldol re-
action?
Product (A) is:
O
(A) O O
O O
(A) (B)
(B)
O
O
(C) (D)
(C) (D) B and C both

O
19. Which acid can be oxidised be Fehling solu-

O3
tion: 22.  (A) Conc . KOH
Zn  
(A) Malonic acid (B) Acetic acid
(C) Oxalic acid (D) formic acid H
(B)  (C) ; Product (C) is

O
e lodoform test
+iv
20. C6 H12 O3 –i v
e Tollens test H
2O
  O
O
drop of H 2SO 4
A (A) (B)
O
Positive Tollen’s Test Compound (A) is : O
O O OCH3
O
(A) CH3– C – CH 2– CH3 (B) CH3 – C – C – CH3 (C) (D)
O
OCH3
(1) O3 / Zn 
O 23. (A) ( 2 ) conc. KOH
  
 OH + HC O2 K
(C) CH3 – C – CH2 – CH – OCH3

HBr (B) major
OCH3 CCl4
Product (B) is
O
(A) (B)
(D) H– C – CH2– CH 2– CH – OCH3
Br Br
OCH3
(C) (D)
O
O
Mel excess
21.  81% yield; Product of the
KH excess

24. (A) KOH


reaction is
O O
HCHO
(B) ; Product (B) is
KOH,
(A) (B)
O O
O
O (A) (B)
O
(C) (D)
(C) (D)
29. Arrange these compounds in decreasing order

OH
of reactivity for the nucleophilic addition reac-
KCN tion:
25. (A) 
 ; Product (B) is
H (l) Acid chloride (ll) Aldehyde
CN
(lll) Ketone (lV) Ester
Select the correct answer from the codes given
below:
Ph–CH=O (A) l > ll> lll > lV (B) lV > lll > ll > l
(B)
KOH,  (C) lll > ll > l > lV (D) l > lV > ll > lll
(A) Ph – CH = CH – Ph
(B) Ph – CH = CH – CH = O 30. Acetal or ketal is:
(A) Vic dialkoxy compound
(C) (D) (B)  ,  -dialkoxy compound
Ph
(C)  -alkoxy alcohol
(D) Gem dialkoxy compound
26. (A) Positive

tollen 's test
O
Na 2 CO 3
31.   Product (A) is
Ph–CH=O 
(B) ; Product (B) is
(A) Ph – CH = C – CH3 O O
O CH3
CH3 (A) (B)
(B) CH–Ph (C) Ph – C =CH –Ph
O O
(D) Ph – CH = CH – CH = O OH
(C) (D)
27. Gem dilhalide on hydrolysis gives:
(A) Vic diol (B) Gem diol
32. In the given reaction:
(C) Carbonyl compound
(D) Carboxylic acid C

Na OH / H
28. Ph – CO2H + CH3CO2H C6H5– O–H 2   [x] , [x] will be:
CaO/ (A) Only syn oxime

(B) Only anti oxime
O O (C) Mixture of syn and anti oxime
(D) Secondary amide
(A) Ph–C–Ph (B) Ph – C – CH3
O 33. Schiff’s base is prepared from:
(A) Carbonyl compound and primary amine
(C) (D) All
(B) Carbonyl compound and secondary amine
(C) Carbonyl compound and tertiary amine
(D) All of these
34. Schill’s reagent is used for the differentiation O

between:
(A) HCHO and CH3CHO 37. D– C –D 50
% 
KOH
 Order of the reaction is :
(B) CH3COCH3 and CH3CHO
(A) 2 (B) 3
O O (C) 4 (D) 1
38. In the reaction

(C) C6H5 – CH2 – C – CH3 and C6H5 – C –CH2–CH3 HO
NaOH
(D) HCHO and C6H5CHO X+ Y   CH3– CH—CH – CHO
5 C
35. I n the reaction sequence[ X] is ketone: CH 3

(X) and (Y) will respectively be:

[ X] KMnO
 4 /
OH / 
 HOOC – (CH2)3–CH2–COOH (A) CH3–CH2–CHO and CH3–CH2–CHO
(B) CH3–CHO and CH3–CH2–CHO
[X] will be: (C) CH3–CHO and CH3–CHO
CH3
O O
CH3 (D) CH3–CHO and CH3–C–CHO

(A) (B)
CH3
O O 39. Total number of products in the given reaction

: (excluding steroisomers)
H3C 
CH3 CH3 OH
(C) (D) C6H5CHO+CH3–CHO  Product will be

(A) One (B) Three
(C) Two (D) Four
36. In the given reaction 40. In the reaction:

O O O 
+ O
H/
 [X] will be
O
SeO
 2  [x] OH OH OH
[X] will be : (A) (B)

O O
O O O
CHO
(A) (B) OH
(C) (D)
O
O
41. Product of Perkin reaction is :
CH3
(A) ,  -unsaturated aldehyde
CH3
(C) (D) (B)  -cyclohexyl ,  -unsaturated aldehyde
O
O (C)  -Aryl- ,  -unsaturated acid
(D) All of these
42. The product of the reaction: 46. Cyanohydrin of which compound on hydrolysis
will give lactic acid?
NO2 CHO+(C6H5–CH2CO)2O
(A) C6H5CHO (B) HCHO
C6 H—CH
5 2 COONa/ 
(C) CH3CHO (D) CH3–CH2–CHO
[X]
[X] will be:
(A) C6H5 – CH = CH –COOH 47. Acetaldehyde cannot give:
(A) lodoform test (B) Lucas test
(B) NO2 CH = CH–COOH
(C) Benedict test (D) Tollens test
(C) C 6H 5–CH=C–COOH
OCH2CH3
48. Compound formed by the

NO2 O CHOH
(D) NO2 CH=C–COOH

C 6H 5
reaction of furfural O with ethanol is
CHO
43. Cross cannizzaro reaction is example of
(A)Redox reaction
(A) an aldol (B) an acetal
(B) Disproportionation
(C) Both (A) and (B) (C) a ketal (D) a hemiacetal
(D) Only oxidation
44. Which will give silver mirror test with Tollens

O3
reagent: 49.  (A) Conc
 . KOH
 (B), Product (B) is:
Zn
(A)C6H5CHO (B) CH3–CHO
(C) HCOOH (D) All of these
(A) CH2–OH (B) CO 2H
O CH2–OH CO 2H
P2O 5 CH MgBr
45. C NH2  W 3 

X (C) CH2–OH (D) CO 2
 H 3O
CO 2 CO 2
Ca ( OH ) 2 .l 2
  Y   Z, Z is :
 yellow ppt . y   50. Which of the following will reacts with NaOI ?
O
O
O
(A) C – CH3
(A) CH3 – C – H (B)

O
(B) COOH
O O
(C) (C) (D) All

C
(D)
O NaH,CH3 I Cl
(P)
O=S=O
51.
LDA,CH3 I
(Q) 53. CH3O18H +  (A) CH
 O
3

 (B) Product (B) is
CH3
Product (P) and (Q) respectively is:
O O
O
(A) (A) CH3–O– S CH 3
O O O
18
(B) CH3 – O – S CH 3
(B)
O
18
(C) CH3– O –CH3 (D)CH3–O–CH3
O O
O
(C)
54. A KOH


 
O O
B KOH
 PH–CH2OH+Ph–C O 2 K

When A reacts with B in presence of KOH /

(D)
 product C is formed product C is ?
(A)Ph–CH=CH–CHO
O
52. Which of the following compound not reacts
with NaHSO3? (B) Ph–CH2–CH2– C –CH3
O O O
(A) H – C – H (B)CH3 – C – H
(C) Ph–CH= CH – C –CH3
O O (D) None
(C) (D)
55. Ph –CH= O+ NH2–NH2 

H (A). Product (A) is
O3 KOH
known as: 58.  (A) 
Zn 
(A) Aldo-Oxime (B) Hydrazone

(B)Major product (B) is:
(C) Hydrate (D) Phenyl hydrazone
O O
56. HO–CH2–CH2–CH=O (

1) KCN
 (A), Product (A) is:
(2) H
( 3) H 3 O 
(4)  (A) (B)
OH
O
O O O
(A) OH (B)
O
O
(C) (D)
O
O
O O
(C) (D) O O
OH OH
59. CH3 – C – CH3 + H – C – H KOH

O O
(A) major. Product (A) is :
57.
2eq.KNH2
  n
 C 4 H 9  Br
 
 (P) O
NH3 (  ) then H 3O O
(A) (B)
End product (P) of above reaction is:
O O O O O HO
(C) (D) O
H
(A) (B)
O
O O O O
60. CH3 – C –OH CaO
 (A) KOH
 
 
(C) (D)
D 2 O / DO 
  (C)
(B) prolonged treatment 
How many hydrogen is replaced by Deuterium

(A) 2 (B) 10
(C) 7 (D) 8
O 62. Product P is .
61. ( i ) KCN

 P OEt OEt
( ii ) H 3O 
H OEt
(A) (B)
Find out the incorrect statement about the OEt
above given reaction
(A) It is a nuclephilic addition reaction
OMe OMe
(B) Obtained product is present in racemic mix-
OPr
ture (C) (D)
(C) If the hydrolysis of obtained product OPr
give  -hydroxy acid
(D) It is a electrophilic addition reaction
63. Product Q is .
Comprehansion : (Q.62 to Q.64):
Aldehydes and ketones react with one mol- O
ecule of an alcohol to form compounds called (A) (B) O
hemiacetals, in which there is one hydroxyl
group and one ether-like group. Reaction of a
hemiacetal with a second molecule of alcohol O
gives an acetal and a molecule of water. We
(C) O (D)
study this reaction
HO
ROH ROH
OR
   
O
H OR H OR
The carbonyl A hemiacetal An acetal 64. Product R is .
group of an (has an—OH and (has two —OR
aldehyde of ketone an—Or group to groups to the
the same carbon) same cabon)
O
O
Draw structural formulas for the hemiacetal and O
(A) O (B)
acetal formed from these reagents. The sto-
ichiometry of each reaction is given in the prob-
lem.
O 
(A) H
+2 CH3CH2OH  (P)
(C) (D)
Cyclohexanone Ethanol
O 
(B) +HOCH2CH2OH H (R)

Cyclohexanone Ethylene glycol

HO O

(C) + H (Q)
HO 
cis-1,2-Cyclohexanediol Acetone
Exercise - II (One or more than one option correct)

1. Which one of the following is mixed ketone (Ali-
phatic & aromatic): 8. Schiff’s reagent gives pink colour with:
O O (A) Acetaldehyde (B) Ph–CH3
(C) Acetic acid (D) Methyl acetate
(A) CH3 – C – CH3 (B) CH3 – CH2 – C – CH3
9. Which of the following compound will give posi-
O O tive Tollens test
(C) Ph – C – CH3 (D) CH3 – C6H4 – C – CH2Ph

(A) CH3CHO (B) O
OH
2. Two isomeric ketones, 3-pentanone and 2-
pentanone can be distinguished by:
(C) CH3CH2CH2CH2 CH –OCH3
(A) l2/NaOH (B) NaSO3H
(C) NaCN/HCl (D) 2,4-DNP OH
OCH3
3. Stability of hydrates of carbonyl compounds (D) CH3– CH
depends on: OCH3
(A) Steric hindrance 10. Mixture of Ph–CHO&HCHO is treated with NaOH
then Cannizzaro reaction involves:
(B) Presence of -1 group on gemdiol carbon
(A) Oxidation of HCHO
(C) lntramolecular hydrogen bonding (B) Reduction of HCHO
(D) angle strain in carbonyl compound (C) Oxidation of Ph–CHO
(D) Reduction of Ph–CHO
4. Whcih of following give positive test with 2,4-
11. PhCHO + HCHO Conc.KOH
DNP?  
O O Correct statement regarding reaction will be
(A) It is an example of redox reaction
(A) CH3– C – H (B) CH3– C –CH3 (B) H CHO is oxidised
O (C) It is cross cannizato reaction
(D) Ph–CHO is reduced
(C) CH3– C –OH (D) CH3–CH2–OH Paragraph for Question Nos.12 to 14

Carbonyl group show characteristic reaction of nu-
5. Fehling solution gives red precipitate with: cleophilic addition in which nucleophile attack in
(A) Aromatic alehyde(B) Aliphatic aldehyde rate determing step on carbonyl carbon.
12. Which Ph is suitable for oxime formation
(C) Ketones (D)  -hydroxy ketones (A) 4–5 (B) 1–2
(C) 8–10 (D) 12–14
6. Silver mirror test with Tollens reagent is given
by : 13. Which of the reactant show geometrical isom-
(A) C6H5CHO erism when it react with hydrazine (NH2–NH2)
(B) Ph–CH2–CHO O
O O
(C) C6H5–CH2– C –CH2OH (A) (B)

(D) CH3CHO
H H
O
7. Which one of the following compounds will not O
give aldol:
(A) Acetaldehyde (B) Formaldehyde (C) (D)
(C) Pivaldehyde (D) Crotonaldehyde
16. Match the following :

CH=O Column l
PCl
O
14. 5 
C–OH H 
(A) + 
N 
O H
OH
w PhMgBr
  x NH
2 NH 2
 y
NH Ph 
Identify final product ‘y’ of the above given H

(B) 
reaction: (–H2 O)
O
NH2
(A) (B)
Ph (C) + 
Ph
O
N N
N
(C) N (D) (D) + NH2 – NH2 
Ph Ph
Column ll
(P) An enamine will form
(Q) Schiff base will form
15. Match list-l with list-ll and select the correct (R)Hydrazone will form
(S) Product form willundergo Lassign test
answer using the codes give below the lists: 17. Column l
List-l O
OH
(A) CH2=CH–CHO NaBH

4  (A)
O
OH
(B) C6H5CHO+Ph–NH2 H

(B)
(C)C6H5COCH3+CH3–CH2–NH2 
H

OH
H  (C)
(D) RCHO+2RCH2OH 
OH Cl
List-ll
(D)
(P) Acetal
(Q) Schiff’s base
Column ll
(R) Unsaturated alcohol (Reagent used)
(P) Al(OCHMe2)3 or H2/Ni
(S) Enamine
(Q)Al(OCMe2)3 or CrO3
(R) H3PO4/ 
(S) conc. HCl
Exercise - III Subjective Level-I

1. Predict the product of the reaction of propanal
3. (a) Arrange the follwong compounds in
with each of the following
decreading order of Keq for hydrate formation.
(a) Lithium aluminum hydride
(b) Sodium borohydride O
(c) Hydrogen(nickel catalyst
C6H5COCH3 Cl C–CH3
(d) Methylmagnesium iodide, followed by dilute acid. ; ;
(1)
(e) Sodium acetylide, followed by dilute acid (2)
(f) Phenyllithium, followed by dilute acid O O
(g) Methanol containing dissolved hydrogen chloride
(h) Ethylene glycol, p-toluenesulfonic acid, benzene
NO2 C –CH3 ; CH 3 C –CH3
(i) Aniline (C6H5NH2)
(j) Dimethylamine, p-toluenesulfonic acid, benzene (3) (4)
(k) Hyderoxylamine
(b) Equilibrium constants for the dissociation
(l) Hydrazine (Kdiss) of cyanohydrins according to equation
(m) Product of part(l) heated in triethylene glycol with
sodium hydroxide OH O
(n) p- Nitrophenylhydrazine
(o) Semicarbazide RCR' Kdiss
RCR' + HCN
+ –
(p)Ethylidenetriphenylphosphorane [(C6H5)3P–CHCH3] CN
(q) Sodium cyanide with addition of sulfuric acid Cyanohydrin Aldehyde Hydrogen
(r) Chromic acid or ketone cyanide
have been measured for a number of cyano-
hydrins. Which cyanohydrin in each of the fol-
2. Give structure for the products of the reactio
lowing pairs has the greater dissociation con-
when butanal is treated with each of the fol-
stant?
lowing reagents
  OH OH
(a) A g(NH3) O H then HOH / H 
(i) CH3CH2 CHCN or (CH3)2 CCN

(b) O H/HOH, 
OH OH

(c) NH2OH/ H
(d) C6H5Li then HOH (ii) C6H5 CHCN or C6H5 CCN

CH3
(e) C6H5CHO, O H, 

(f) CHCNa then HOH / H
4. Some grignard reagents react with ethyl

(g) CH2OH– CH2OH, H orthoformate followed by acidic hydrolysis to
give aldehydes. Propose mechanisms for the
(h) SH–CH2–CH2–CH2–SH then Raney Ni/H2
two steps in this synthesis.
(i) CH3MgBr then H2O
(j) HCN O–CH2CH3 O–CH 2CH O
(k) NaBH4 H3O +
H–C–O–CH2CH 3+R–Mg–X R–C–O–CH2CH 3 R–C–H

Br
O–CH2CH3 H

(l) CH3–CH2– CH–COOC2H5 and Zn then H2O/ H ethyl orthoformate acetal aldehyde
(Reformatsky reaction)
5. Suggest a reasonable mechanism for each of 9. Give the structure of the substance for each
the following reactions: of the following reaction :
O O
O
(CH3)3 C
C CH2 NaOCH
 3  (CH ) CCCH OCH
CH 3 OH 3 3 2 3
Cl (88)% (a) (x) NaOH

 /

6. Predict the organic products:

O O
(a) CH3 – C – CH3 + HO – CH2–CH2–NH2 H

2 / Pt
 C — CH3
(b) (Y) NaOH
 /

CH3
CH2—CH2—CH2—NH2
(b) H
2 / Pt

O 
(c) (Z) NaOH

 /
 O
O
(c) —C—CH3 (

i ) Cl 2 / NaOH / HOH
  
( ii ) H 10. Each of the following reactions has been re-
ported in the chemichal literature. Write the
structure of the product(s) formed in each
7. A synthesis that begins with 3,3 - demethyl- case.
2-butanone gives the epoxide shown.Suggest
O
reagents appropriate for each step in the syn-
Soft 
thesis. C 6 H 5CH 2SH
O O
(a) H C
3
CH 2   
NaOH , H 2 O
(a) (CH3)3C C CH3 58


 % (CH3)3C C CH2Br O
O
C6H 5
OH (b) Cl CH +
O C6H 5
68%
54

 % (CH3)3C CCH2Br 
(CH3 )3 CC CH 2
H
KOH

ethanol
(b) Overall yield of the reaction is
8. Outline resonable mechanisms for each of the

following reactions:
O O
CH2CH2CH2CH2Br
KOC
 ( CH 3 ) 3


benzene
(76%)
Exercise - IV (A) JEE- PROBLEMS

Single Choice Question : 8. In the reaction P is [JEE 1995]
1. The reagent with which both acetaldehyde and
acetone react easily is [JEE 1982] CH 3
SeO2
(A) Tollen reagent (B) Schiff reagent CO   P  Se  H2O
(C) Grignard reagent (D) Fehling reagent CH 3
2. The Cannizzaro reaction is not given by (A) CH3COCHO (B) CH3COOCH3

(A) trimethyl acetaldehyde[JEE 1983] (C) CH3COCH2OH (D) None
(B) acetaldehyde
(C) benzaldehyde 9. In the Cannizzaro reaction given below, 2Ph–
(D) formaldehyde CHO OH
 –
 Ph–CH2OH+PhCO2 the slowest
3. When acetaldehyde is heated Fehling solution step is : [JEE 1996]
–
it gives a precipitate of [JEE 1983] (A) the attack of OH at the carbonyl group
(A) Cu (B) CuO (B) the transfer of hydride to the carbonyl group
(C) Cu2O (D) Cu+Cu2O+CuO (C) the abstraction of proton from the car-
boxylic acid
4. m-chlorobenzaldehyde on reaction with conc. (D) the deprotonation of Ph–CH2OH
KOH at room temperature gives:
10. In a Cannizzaro reaction the intermediate which
[JEE 1991] is the best hydride donor is: [JEE 1997]
(A) Potassium m- chlorobenzoate and
m-hydroxybenzaldehyde H H
(B) m- hydroxybenzaldehyde and
m- chlorobenzyl alcohol (A) C6H5 – C – O– (B) C6H5 – C – O–
(C) m- chlorobenzyl and m- hydroxybenzyl
alcohol OH O
—
(D) Potassium m- chlorobenzoate and

m- chlorobenzyl alcohol H
H
5. Hydrogenation of benzoyl chloride in the O—
O— —
presence of Pd and BaSO4 gives: (C) (D) O
O— CH3O
[JEE 1992] O2N
(A) Benzyl alcohol (B) Benzaldehyde
(C) Benzoic acid (D) Phenol 11. CH3CHO+H2NOH  CH3–CH=N–OH. The above
reaction occurs at: [JEE 1997]
6. An organic compound C3H6Odoes not give a
precipitate with2,4- Dinitropheyl hydrazine (A)pH=1 (B) pH=4.5
reagent and does not react with metallic (C) Any value of pH (D) pH = 12
sodium. it could be: [JEE 1993]
12. Which of the following will undergo aldol con-
(A) CH3CH2CHO (B) CH3COCH3 densation: [JEE 1998]
(C) CH2=CH–CH2OH (D) CH2=CH–O–CH3
(A) Acetaldehyde (B) Propanaldehyde
(C) Benzaldehyde (D) Trideutero acetalde-
7. Under Wolff Kishner reduction conditions, the hyde
conversions which may be broght about is?
13. Whcih of the following will react with water:
[JEE 1995]
[JEE 1998]
(A) Benzaldehyde into Benzyl alcohol
(B) Cyclohexanol into Cyclohexane (A) CHCl 3 (B) Cl3CCHO
(C) Cyclohexanone into Cyclohexanol
(D) Benzophenone into Diphenylmethane (C) CCl4 (D) ClCH2CH2Cl
14. A mixture of benzaldehyde and formaldehyde

CH2OH COOH
on heating with aqueous NaOH solution gives:
[JEE 2001]
(A) benzyl alcohol and sodium formate
(B) sodium benzoate and methyl alcohol (C)
(C) sodium benzoate and sodium formate CH2OH
COOH
(D) benzyl alcohol and methyl alcohol
O
15. 1- propanol & 2- propanol can be best distin-
guished by: [JEE 2001] O
(A) Oxidation with alkaline KMnO4 followed by
reaction with Fehling solution
(B) Oxidation with acedic dichromate followed
by reaction with Fehling solution (D)
(C) Oxidation by heating with copper followed O
by reaction with Fehling solution
O
(D) Oxidation with concentrated H2SO4 followed
by reaction with Fehling
16. Compound A (molecular formula C3H8O) is 18. The products of acid hydrolysis of P and Q can
treated with acidified potassium dichromate to be distinguished by [JEE 2003]
form a product B (molecular formula C3H6O). B
forms a shining silver mirror on warming with CH3
ammonical silver nitrate. B when treated with OCOCH3
an aqueous solution of H2NCONHNH2. HCl and P=HC=
2
Q=
sodium acetate gives a product C. ldentify the CH3 OCOCH3
structure of C. [JEE 2002]
(A) CH3CH2CH = NNHCONH2 (A) Lucas reagent (B) 2,4-DNP
(C) Fehling solution (D) NaHSO3
(B) CH3–C=NNHCONH2
CH3
2 
19. Ph–CC– CH3 Hg
 /H
 A [JEE 2005]
(C) CH3–C=NCONHNH2
CH3 O
(D) CH3CH2CH= NCONHNH2 Ph Ph O
(A) (B)
CHO OHC CH 3
CH3
17. (
i ) NaOH ( excess )100 C
   
( ii ) H / H 2 O
O
CHO OHC
any one of the products formed is: (C) Ph (D) Ph
[JEE 2003] OH
COOH HOOC CH3 CH 3
(A) COOH
CHO
COOH HOOC
CH3COONa
20. +X
CH2OH MeO
MeO
CH2OH
What is X ? [JEE 2005]

(B) (A) CH3COOH (B) BrCH2,COOH
CH2OH (C) (CH3CO)2O (D) CHO—COOH
CH2OH
21. How will you convert butane-2-one to 25. Statement -1 : Glucouse gives a reddish- brown
propanoic acid? [JEE 2005]
precipitate with Fehling’s solution. because
(A) Tollen reagent (B) Fehling solution
(C) NaOH / I2/H+ (D) NaOH/NaI/H+ Statement -2 : Reaction of glucose with
fehling’s solution gives CuO and gluconic acid.
22. The smallest ketone and its next homologue [JEE 2007]
are reacted with NH2OH to form oxime.
(A) Statement -1 is True ; Statement -2 is
[JEE 2005]
True; statement-2 is a correct explanation for
(A) Two different oximes are formed
statement -1
(B) Three different oximes are formed
(C) Two oximes are optically active (B) Statement -1 is True; Statement -2 is
(D) All oximes are optically active True; statement-2 is NOT a corrcect expla-
nation for statement -1
23. Which of the following reactats on reaction (C) Statement -1 is True, Statement -2 is
with conc. NaOH followed by acidification gives
False.
the following lactone as the only product?
[JEE 2006] (D) Statement -1 is Fals, Statement -2 is True.
MCQ:
C
O
26. Match the compounds/ion in column l with their
CH2
properties / reaction in Cloumn ll. Indicate your
answer by darkening the appropriate bubbles
COOH of the 4  4 matrix given in the ORS.

COOCH3
(A) (B) [JEE 2007]
COOH CHO
Column l
CHO COOH (A) C6H5CHO
(C) (D) (B) CH3C  CH

CHO COOH
(C) CN–
(D) l–
24. Cyclohexene on oxonolysis followed by reac-
tion with zinc duct and water gives compoundE. Column ll
Compound E on further teratment with aque-
ous KOH yields compound F. Compound F is (P) give precipitate with 2,4-
[JEE 2007] dinitrophenylhydrazine
(Q) gives precipitate with AgNO3

(A) CHO (B) CHO
(R) is a nucleophile
(S) is involved in cyanohydrin formation

CO2H
(C) COOH (D)
CO2H
27. Match the compound in Column l with their 28. Compound H is formed by the reaction of
O
characteristic test (s)/reaction(s) given in Col-
umn ll. lndicate your answer by darkening the
(A) + PhMgBr
appropriate bubbles of the 4  4 matrix given in Ph CH3
the ORS [JEE 2008] O
Column l
  (B) + PhCH2MgBr
(A) H2N – N H3 Cl Ph CH3
O
 
N H3 I (C) + PhCH2MgBr
(B) HO H
COOH Ph
O Me
(D) +
  Ph H Ph MgBr
(C) HO NH3 Cl
29. The structure of compound l is

(D)
  H 3C
O2N NH— NH3 Br Ph CH 3 Ph
NO2 (A) (B)

H Ph H Ph
Column II
Ph CH3 H 3C
(P) sodium fusion extract of the compound CH 3
gives Prussian blue colour with FeSO4 (C) (D)

H CH2Ph H
(Q) gives positive FeCl3 test Ph
(R) gives white precipitate with AgNO3

(S) reacts with aldehydes to form the corre 30. The structures of compounds J,K and
sponding hydrazone de rivative L,respectively are
Paragraph for Question No. 28 to 30 (A)PhCOCH3,PhCH2COCH3 and PhCH2COO–K+
(B) PhCHO,PhCH2CHO and PhCOO–K+
A tertiary acohol H upon acid catalysed dehydration (C) PhCOCH3, PhCH2CHO and CH3COO–K+
gives a product l. Ozonolysis of l leads to (D) PhCHO,PhCOCH3 and PhCOO–K+
compounds J and K compound J upon reac-
tion with KOH gives benzyl alcohol and a com- Paragraph for Question Nos. 31 to 34
pound L, whereas K on reaction with KOH gives A carbonyl compound P, which gives positive
iodoform test, undergoes reaction with MeMgBr
only M. [JEE 2008] followed by dehydration to give an olefin Q.
Ozonolysis of Q leads to a dicqarvonyl com-
pound R which undergoes intramolecular aldol
O reaction to give predominantly S.
Ph [JEE 2009]
H3 C
M= 
P 1
. MeMgBr 3
 Q  R 1
. OH 1. O
 S
Ph H 
2. H , H 2 O 2.Zn,H2O 2. 
3. H 2SO 4 , 
31. The structure of the carvonyl compound P is

O
Me
O
(A) (B)
Me
Me
O
O Me (C) (D)
O
Me Me
(C) (D) Paragraph of Question Nos. 34 to 36

O Et
Et Two aliphatic aldehydes P and Q react in the
presence of aqueous K2CO3 to give compound
32. The structures of the products Q and R, re- R which upon treatment with HCN provides
spectively are compound S. On acidification and heating. S
O gives the product shown below
[JEE 2010]
Me H H3C OH
(A) , COMe
H3C
Me Me
Me Me O O
O
34. The compounds P and Q respectively are -
H
CH3
(B) , CHO
Me Me H3C H
Me Me CH
H C
O (A) H3C C and
O
O
H
(C) , CHO
Me Et CH3
Me Et
H H
O CH
H C
Me (B) H3C and
C
CH3 O
O
(D) , CHO
Me Me Et
CH 2 H3C H
33. The structure of the product S is : H 3C
H
O CH C C
(C) and
O O
CH3
(A) (B)
CH 2 H H
O H 3C
Me H
Me Me
CH C C
(D) and
O O
CH3
35. The compound R is

36. The compound S is
O
O
CH3
HC C
H CH C
(A) C H
H3 C (A) H3C CH
H 2C H 2C
OH
CN
O O
H3 C C C
C H H3C
(B) H C (B) C H
3
CH H3C
OH H2 C
H3 C CN
O
CH 3 CH 3 CN
CH C CH CH
(C) HC
3 CH H (C) H3 C CH OH
CH 2 H 2C
OH OH
O
CH3 CN
CH CH CH
H (D) H3 C
(D) H3 C CH C OH
H3 C
CH CH 2
OH OH
H3 C
Exercise - IV (B)
1. Outline the reaction sequence for the conver-
CHO
sion of methanal to ethanal (the number of
steps should not be more than three). ( i ) dil . NaOH
8. + CH3CHO (
ii ) 
 (X) Major Product
[JEE 1981]
ldentify the major product with suitable

2. Benzaldehyde undergoes aldol condensation in
mechanism?
an alkaline medium [True or False]
9. Fehling solution A consists of an aqueous so-
[JEE 1982] lution of copper sulphate, while Fehling solu-
tion B consists of an alkaline solution ________
3. An alcohol A when heated with conc H2SO4 [JEE 1990]
gives an alkene B. When B is bubbled through 10. Write the structure of the major organic prod-
bromine water and the product obtained is uct expected form the following reaction.
dehydrohalogenated with excess of sodamide
a new compound C is obtained. Compound C CH3O CHO + HCHO
KOH

gives D when treated with warm dilute H2SO4
in the presence of HgSO4. D can also be ob- [JEE 1992]
tained either by oxidising A with KMnO4 or
11. Suggest appropriate structures for the missing
from acetic acid throgh its calcium salt. ldentify
compounds. (The number of carbon atoms re-
A,B,C and D. [JEE 1983]
mains the same throughout the reaction)
[JEE 1996]
4. Show with balanced equation what happens
CH3
when the following are mixed:

“Chloral is heated with aqueous sodium hy-
dil
KMNO
4  A HIO
4  B OH
 C
droxide” [JEE 1984] CH3
12. Acetophenone on reaction with hydroxylamine-

5. Write the reactons involved in the preparation hydrochloride can produce two isomeric oximes.
of the following using the reagents indicated Write structures of the oximes.
against in parenthesis. [JEE 1984] [JEE 1997]
“Propionic anhydride from propionaldehyde”
13. Five isomeric para -disubstituted aromatic com-
(AgNO3,NH4OH,P2O5) pounds A to E with molecular formula C8H8O2
were given for identification. Based on the fol-
6. Write the main product of the following lowing observations, give structure ofthe com-
pounds. [JEE 2002]
reacton: [JEE 1985]
(i) Both A and B form a silver mirror with Tollen’s
NaOH reagent; also, B gives a positive test with FeCl3
Propanal 
heat
solution
(ii) C gives positive iodoform test.
7. How can the following transformation be car- (iii) D is readily extracted in aqueous NaHCO3
solution.
ried out (in not more than six steps) “ Benzal-
(iv) E on acid hydrolysis gves1, 4-
dehyde to cyanobenzene”? [JEE 1986]
dihydroxybenzene.
16. Which ofthe following disaccharide will not re-

14. C6H12 HCl
 C6H13Cl + (C)
duce Tollen’s reagent ? [JEE 2005]
(A) (B) CHOH
CHOH
2 2
HO O H H O HO
H HO H OH
Alc.KOH (D) ozonolysis
  (E) (A) H O H
(—HCl) OH H
OH H
ozonolysis NaOH
(Q) CH2 OH
(A) (F) + (G) HCOONa+1°alcohol HOH2C
HO O H H O OH
H HO OH H
(D) is isomer A. E gives negative test with H H
(B) O
Fehling solution but gives iodoform test F and OH H H OH
G gives Tollen’s test but do not give iodoform
(P)
test. ldentify A to G. [JEE 2003]
O
OH
15. Give major product A, B,C and D in following  (i) O NaOH
reaction sequence. [JEE 2004]
17. H
,
 X 3  Y 
( ii ) Zn / Cl 3 COOH
CH2–Cl
Identify (X) and (Y) [JEE 2005]
KCN (i) NaOEt/EtOH

(A) 18. In the scheme given below the total number of
DMF
intramolecular aldol condensation products
formed from Y is [JEE 2010]
(B) H3 O (i) SOCl2
(C)
(ii) CH 3–NH2 1
.O 3
 1. NaOH ( aq )
Y  
2. Zn , H 2 O 2. heat
Answers
Exercise-I
1. B 2. C 3. D 4. B 5. D 6. D 7. B
8. C 9. D 10. C 11. A 12. D 13.(i)C(ii)C 14. B
15. D 16. B 17. A 18. A 19. D 20. C 21. C
22. A 23. B 24. B 25. B 26. D 27. C 28. D
29. A 30. D 31. A 32. C 33. A 34. B 35. A
36. B 37. B 38. B 39 C 40. D 41 C 42. D
43. A 44. D 45. C 46. C 47. B 48. D 49. C
50. D 51. C 52. D 53. D 54. C 55. B 56. A
57. D 58. B 59. C 60. B 61. D 62. B 63. B
64. B
Exercise-II
1. C,D 2. AB 3. A,B,CD 4. A,B 5. B,D 6. A,B,C,D 7. B,C

8. A 9. A,B,C 10. A,D 11. A,B,C,D 12. A 13. D 14. C
15. A–R ; B – Q ;C – Q; D – P 16. A  P,S ; B  Q, S ; C  Q, S ; D  R , S
17. A  P ; B  Q ; C  R ; D  S
Exercise-III
1. (a) CH3—CH2—CH2—OH (b) CH3—CH2—CH2—OH (c) CH3—CH2—CH2—OH

OH OH OH
(d) CH3—CH2— CH —CH3 (e) CH3 —CH2— CH —CCH (f) CH3 —CH2— CH — Ph
O
(g) CH3—CH2— CH —OCH3 (h) CH3–CH2–CH (i) CH3—CH2—CH= N —Ph
O
OCH 3
OH
(j) CH3 —CH2— CH — N —CH3 (k) C—C—C=N—OH (l) CH3—CH2—CH=N—NH2

CH3
(m) CH3—CH2—CH3 (p) P-Nitro phenyl hydrazone (o) semi carbazane

OH
(p) CH3—CH2—CH=CH—CH3 (q) CH3—CH2— CH —CN (r) CH3—CH2—CO2H
O
2. (a) C—C—C— C —OH (b) CH3–CH2–CH2–CH=C–CH2–CH3 (c) C—C—C—C—C=N—OH

CHO OH
OH
(d) C—C—C— C–Ph (e) Ph–CH=C–CH 2–CH3 (f) C—C—C— CH —CCH
O CHO
(g) C—C—C—C (h) C—C—C—C (i) 2º alcohol
O
OH
(j) Cyanohydrine (k) 1° alcohol (l) CH3—CH2—CH2— CH — CH—CO2H
Et
3. (a) 3 > 2 > 1 > 4 4. R —Mg—X

OH OH
(b) (i) (CH3)2 CCN (ii) C6H5 CCN
CH3
•• •••
•
(CH3)3C O O
5. C CH2 OCH3 (CH3) 3C
Cl C–CH2OCH3
Cl
O
(CH3)C–C–CH2OCH3
O
6. (a) CH3— CH —NH—CH2—CH2—OH (b) (c) CHCl3 + C— OH

N
CH3 |
H
7. HO  /Br2; H2/Ni; NaOH
O O O
CH2CH2CH2CH2–Br CH2 CH2 CH2 CH2 –Br



Acid Base reaction
8.
(CH3)3CO
O
O CHO
C— CH 3
9. (a) (X) CH3 (Y) (b) CH2—C—CH3
CHO O CH3 O
O Ph
CH =
Ph
10. (a) CH CH—S—CH—Ph
2
(b)
3 2
Cl
Exercise-IV (A)
1. C 2. B 3. C 4. D 5. B 6. D 7. D
8. A 9. B 10. D 11. B 12. ABD 13. B 14. A
15. C 16. A 17. C 18. C 19. A 20. C 21.C
22. B 23. C 24. A 25. C
26. A  P,Q,S;B  Q,R;C  Q,R,S;D  Q,R
,R
27. A—R,S;B—P,Q:C—P,Q,R;D—P,S (OR) A—R; B—P,Q; C—P,Q,R; D—P
28. B 29. A 30. D 31. B 32. A 33. B 34 B

35. A 36. D
Exercise-IV (B)
3 CH MgBr
1. HCHO   CH CH OH
H / H O 3 2
2
CH3CH2OH  PCC
 CH3CHO
2. False
3. A: CH3— CH —CH3
OH
B: CH3—CH=CH2
C:CH3—C  CH
D: CH3COCH3
4. Cl3C–CHO NaOH
 CHCl3+HCOONa
3 4 AgNO /NH OH
5. CH3CH2CHO  CH3CH2COOH
Oxidation
2 5 PO
2CH3CH2COOH 
 (CH3CH2CO)2O
H 2O
O O O
OH

6.  H3C—CH2— CH — CH — C —H 
2 H3C—CH2— C —H NaOH  H C—CH —CH= C — C —H
 H 2O 3 2
CH3 CH3
+ –
CHO COOH NO2 NH2 N2Cl CN
NaOH
KCN
NaNO2
7. PCC
    
 

CaO HCl
CHO
–H2O
CH–CH2–CHO CH=CH–CHO
8. +CH3CHO NaOH

OH
9. sodium potassium tartrate which is known as Rochells salt.
CHO CH2OH
O O
10. + H— C —H 50
% 
NaOH
 + H— C —ONa
OCH3 OCH3
Sodium formate
11. dil
KMnO CH3
4  H3C OH OH
H3C CH3
Hydroxylation
O O
H3C CH3 HIO

4  H3C–C–CH2–CH2–CH2–C–CH3
OH OH
CH 3
O O H3C OH
—
OH –H2O
H3C–C–CH2–CH2–CH2–C–CH3
O O
12. C6H 5–C–CH3 and C6H5–C–CH3
N–OH HO–N
syn anti (isomers)
O
CHO CHO CH2CHO COOH O–CH=CH2
C–CH3
or
13. (A) (B) (C) (D) (E)
OCH3 CH2OH OH CH3 OH

OH
14. Me3C—CH=CH2 HCl

 Me2 C —CHMe2+Me3C— CH–Me
Cl Cl
(A) (B) (C)
alc. KOH
Ozonolysis NaOH
(A) HCHO+Me3C–CHO
(F) (G)
HCOONa+Me3C–CH2OH(1°alcohol)
CONHCH 3
CN COOH
CH2–CN CH = C
CH=C CH=C
15. (A) (B) (C) (D)
(i) SOCl2
(D) (ii) CH3NH2
16. In structure (P) both the rings are present in acetyl form therefore it will not hydrolyse in solution that
why Tollen’s solution connot react with this.
In structure (Q) one ring present in the form of hemiacetal. This will hydrolysed in solution it can reduce
Tollen’s solution.
17. (X) (Y) CH3— C —(CH2)4—CH=O 18. 1
CH3

Carbonyl

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Page # 24 CARBONYL COMPOUNDSE

Exercise - I (Only one option is correct)

O O (x) and (y) are

dil. KOH H Ag

Reagent (x) is Degree of unsaturation in product is?

(C) (D) B and C both

19. Which acid can be oxidised be Fehling solu-

(C) CH3 – C – CH2 – CH – OCH3

29. Arrange these compounds in decreasing order

(B) CH–Ph (C) Ph – C =CH –Ph

CaO/ (A) Only syn oxime

34. Schill’s reagent is used for the differentiation O

38. In the reaction

35. I n the reaction sequence[ X] is ketone: CH 3

CH3 (D) CH3–CHO and CH3–C–CHO

O O 39. Total number of products in the given reaction

36. In the given reaction 40. In the reaction:

[X] will be : (A) (B)

48. Compound formed by the

(D) NO2 CH=C–COOH

44. Which will give silver mirror test with Tollens

(A) CH3 – C – H (B)

(C) (C) (D) All

(A) (A) CH3–O– S CH 3

When A reacts with B in presence of KOH /

55. Ph –CH= O+ NH2–NH2 

(A) Aldo-Oxime (B) Hydrazone

56. HO–CH2–CH2–CH=O (

How many hydrogen is replaced by Deuterium

61. ( i ) KCN

Cyclohexanone Ethylene glycol

Exercise - II (One or more than one option correct)

(C) Ph – C – CH3 (D) CH3 – C6H4 – C – CH2Ph

(C) CH3– C –OH (D) CH3–CH2–OH Paragraph for Question Nos.12 to 14

(C) C6H5–CH2– C –CH2OH (A) (B)

16. Match the following :

(A) CH2=CH–CHO NaBH

Exercise - III Subjective Level-I

H–C–O–CH2CH 3+R–Mg–X R–C–O–CH2CH 3 R–C–H

Cl (88)% (a) (x) NaOH

6. Predict the organic products:

(a) CH3 – C – CH3 + HO – CH2–CH2–NH2 H

(c) (Z) NaOH

(c) —C—CH3 (

(a) (CH3)3C C CH3 58

8. Outline resonable mechanisms for each of the

Exercise - IV (A) JEE- PROBLEMS

2. The Cannizzaro reaction is not given by (A) CH3COCHO (B) CH3COOCH3

(D) Potassium m- chlorobenzoate and

14. A mixture of benzaldehyde and formaldehyde

COOH HOOC CH3 CH 3

What is X ? [JEE 2005]

COOH of the 4  4 matrix given in the ORS.

CHO COOH (A) C6H5CHO

(C) (D) (B) CH3C  CH

(Q) gives precipitate with AgNO3

(S) is involved in cyanohydrin formation

29. The structure of compound l is

NO2 (A) (B)

gives Prussian blue colour with FeSO4 (C) (D)

(R) gives white precipitate with AgNO3

31. The structure of the carvonyl compound P is

(C) (D) Paragraph of Question Nos. 34 to 36