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EXERCISE

Oxygen Containing Compounds

ENGLISH MEDIUM
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® Chemistry : Oxygen Containing Compound
Pre-Medical

EXERCISE-I (Conceptual Questions) Build Up Your Understanding

ALCOHOL 6. Select the incorrect option for the following
1. The compound A, B and C in the reaction reaction:
sequence H+
→ CH3– CH – CH3
CH3– CH = CH2 + H2O
PBr3
CH3CH2OH → A 
→ B 
→C alc.KOH Br2
∆ OH
are given by the set
(1) This is an example of NAR of alkene
(1) C2H5Br, CH3CH2OH, CH3CHBr2.
(2) In the first step, protonation of alkene takes
(2) C2H5Br, CH≡CH, CH2=CHBr
place to form carbocation
(3) C2H5Br, CH2=CH2, CH2Br—CH2Br
(3) In the second step, Nucleophilic attack of
(4) C2H5Br, CH3CH2OH, BrCH2—CH2Br water takes place on carbocation
AE0001
(4) In the last step deprotonation takes place to
2. Which of the following alcohols gives a red form an alcohol

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colour in Victor Meyer test HC0201
(1) CH3–CH2–CH2–OH 7. For the reduction of aldehydes and ketones into
(2) CH3–CH–OH alcohol the reagent which can be used is/are :
CH3 (1) H2 in presence of Ni, Pt or Pd

(3) (CH3)3C–OH (2) NaBH4

(4) CH3–CH–CH2–CH3 (3) LiAlH4

OH (4) All of these

AE0003 CC0202
8. Which of the following does not reduces the
3. Which of the following does not turn orange
colour of chromic acid to green carboxylic acids into alcohol ?
(1) 1° alcohol (2) 2° alcohol
1.LiAlH4/ether 1.B2H6
(3) 3° alcohol (4) Allyl alcohol (1) (2) +
2.H3O
+
2.H3O
AE0005

4. p, s and t-alcohols can be distinguished by :- ROH H2

(3) NaBH4 (4)
(1) Reimer-Tiemann reaction H+ Catalyst
(2) Tollen's reagent
(3) Lucas test CA0203
(4) Lassaigne's test
AE0006 H2SO4
A
443K
5. Consider the following reaction : 9. CH3CH2OH A and B are
C2H5OH + H2SO4 → Product H2SO4
B
Among the following, which one cannot be 413K
formed as a product under any conditions ? (respectively)

(1) C2H5OSO3H (1) O , CH2 = CH2

(2) H2C=CH2
(2) O , O
(3) HC≡CH
(4) CH3–CH2–O–CH2–CH3 (3) CH2 = CH2, CH2 = CH2
AE0007 (4) CH2 = CH2, O
AE0204
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10. Which of the following is insoluble in water ? 15. The reaction
(1) Ethanol (2) Ethoxyethane
(3) Phenol (4) Pentane OH
AE0206 ⊕
⊕ 140° C
PHENOL ONa+CO
2

→ COONa

11. Nitration of phenol with conc. H2SO4 followed by

is called :-
nitric acid gives :-
OH OH (1) Schotten Bauman reaction
NO2 (2) Kolbe Schmidt reaction
(1) (2)
NO2 (3) Reimer–Tiemann reaction
OH OH (4) Lederer–Manasse reaction
O2N NO2 AE0012
(3) (4)
16. Phenol can be distinguished from ethanol by

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NO2 NO2 reactions with the following except :-
AE0008
12. Deoxygenation of phenol can be achieved by (1) Iodine and alkali
distillation with :- (2) Ferric chloride
(1) Raney nickel
(2) Lithium aluminium hydride (3) Acetyl chloride
(3) Sodium borohydride
(4) Zinc dust (4) Bromine water
AE0009 HD0013
13. Which of the following compounds shows
intramolecular hydrogen bonding :- 17. Phenol on treatment with methyl chloride in the
(1) p–Nitrophenol (2) Ethanol
(3) o–Nitrophenol (4) Methanamine presence of anhydrous AlCl3 gives chiefly :-
AE0010 (1) o–cresol (2) m–cresol
O Na⊕
O (3) anisole (4) p–cresol
14.
+ CH3—C—Cl ? AE0014
Sodium phenate 18. Phenol on heating with NaNO2 and a few drops
O
of conc. H2SO4 mainly gives :-
C–OCH3
(1) p–nitrophenol
(1)
(2) p–nitrosophenol
O (3) o–nitrophenol
OH
C–CH3 (4) m–nitrosophenol
AE0015
(2)
O 19. Phenol and benzoic acid are distinguished by :-
O–C–CH3 (1) Lucas reagent
(3) (2) Victor Meyer test
(3) Caustic soda
Cl
(4) Sodium bicarbonate
(4) PO0016
CA0011
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20. Phenol on treatment with dil HNO3 at low temp 23. In the reaction sequence
(298 K) gives two products P and Q. P is steam HBr C2 H5 ONa
volatile but Q is not. P and Q are respectively. A  → B → Ethoxyethane,

OH OH A and B are :-
NO2 (1) C2H6, C2H5Br
(1) and
(2) CH4, CH3Br
NO2
(3) CH2=CH2, C2H5Br
OH OH
(4) CH≡CH,CH2=CHBr
(2) and
AE0021
NO2
NO2 H ⊕
24. CH3–CH2–OH + Ph–CH2–OH 
140° C

→ of
OH OH
OH NO2 which is not obtained?

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(3) and (1) CH3–CH2–OCH2–CH3

NO2 OH (2) Ph–CH2–OCH2–Ph

OH OH (3) Ph–CH2–O–CH2–CH3

(4) Ph–CH2–O–CH2–O–CH3
(4) and
NO2 AE0023
NO2
AE0207 25. Oxonium ion of ether has the structure :-
ETHER ⊕
(1) C2H5–O–CH–O–H
21. The preparation of ethers from alcohols by using
CH3 H
sulphuric acid is called :-
(1) Williamson's ether Synthesis ⊕
(2) CH3–CH2–O–CH2–CH3
(2) Williamson's continuous etherification process
(3) Ziesel's method H
(4) Zerewitinoff method (3) (C2H5)2O → O
AE0236
⊕
22. PBr3 Mg/ether H2O/H+ (4) CH3–CH2–O–CH2–CH2–CH2–O–O–H
CH3–CH–CH3 X Y
H
OH

The final product is :- AE0024

(1) CH3–CH–OH 26. Which of the following does not react with aq.
CH NaOH :-

(2) CH3–CH2–CH2–OH (1) Phenol

(3) CH3–CH–O–CH–CH3 (2) Benzoic acid

CH3 CH3 (3) CH3COOH

(4) CH3–O–C6H5
(4) CH3–CH2–CH3
AE0020 PO0026

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27. A student tried two reactions for preparing tert- Cl
butyl ethyl ether : 32. Ph–C–CH3 + aq. KOH → A →→ B?
KCN
⊕
H
CH3
Cl
(I) C2H5ONa + CH3 – C – Cl (1) 50% d + 50% l (2) 80% d + 20% l
CH3 (3) Meso compound (4) optically active
CC0032
CH3
O
(II) CH3 – C – ONa +CH3 – CH2– Cl
33. C can be obtained by :-
CH3

Which reaction will give better yield of tert butyl O

ether ?
C—Cl + (Ph)2Cd
(1) Only I (2) Only II (1)
(3) Both I & II (4) Neither I nor II

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O OH
HD0208
C—Cl
CARBONYL COMPOUNDS (2) +
28. Acetaldehyde on warming with Fehling's solution
gives a red precipitate of :- (3) + CO + ZnCl2 + HCN
(1) Elemental copper
(4) None of the above
(2) Cuprous oxide
CC0033
(3) Cupric oxide
(4) Mixture of all of the above 34. Which does not react with NaHSO3.
CC0027
(1) Ph–C–H
O
29. Acetone does not form :-
(1) A phenylhydrazone with phenylhydrazine CH3–O C–H
(2)
(2) A sodium bisulphite adduct with sodium O
bisulphite
(3) A silver mirror with Tollen's reagent (3) CH3 CH2–C–Ph
(4) An oxime with hydroxylamine O
CC0028 CHO
(4)
30. CH3CHO and CH3COCH3 can not be CH3
distinguished by :- CC0034
(1) Fehling solution 35. Ketones can be prepared by :-
(2) Grignard reagent (1) Rosenmund reduction
(3) Schiff's reagent (2) Etard reaction
(4) Tollen's reagent (3) Cannizzaro reaction
CC0029 (4) Friedel-Craft reaction
CC0035
31. Acetone is obtained by the hydrolysis of the
36. Carbonyl compounds are best purified by :-
addition product of methyl magnesium iodide
(1) Steam distillation
and:-
(2) Hydrolysis of sodium bisulphite adducts
(1) HCHO (2) CH3CHO (3) Fractional crytallisation
(3) CH3COCH3 (4) CH3–C≡N (4) Sublimation
CC0031 CC0036

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37. Carbonyl compounds readily undergo :- 43. Which of the following can be converted to
CH3–CH=CH–CHO :-
(1) Nucleophilic substitutions
(1) Acetone (2) Acetaldehyde
(2) Electrophilic addition reactions
(3) Propanaldehyde (4) Formaldehyde
(3) Nucleophilic addition reactions
CC0045
(4) Free radical substitution reactions 44. The product of reaction with primary amine and
CC0037 aldehyde is -
O
O O
38. and are readily (1) R–C–OH (2) R–ONO
CH3–C–CH3 CH3–C–H
(3) R'–CH=N–R (4) R–NO2
distinguished by their reaction with :- CC0046
(1) Iodine and alkali 45. Brady's reagent is
(2) 2,4-dinitrophenylhydrazine (1) [Cu(NH3)4]SO4
(3) Tollen's reagent (2) KMnO4/NaIO4

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(4) All the above NO2

CC0038 (3) O2N NH.NH2

39. Which is the most suitable reagent for the NO2

following conversion (4) O2N F
O O
CC0047
CH3–CH=CH–CH2–C–CH3 CH2–CH=CH–CH2–C–OH
(i)Tollen ' s reagent (i) Benzoyl peroxide 46. A compound with molecular formula C3H6O, not
(1)  → (2)  →
(ii)H ⊕ ⊕
(ii)H gives silver mirror with Tollen's reagent but forms
(i) I2 and NaOH
⊕
KMnO4 / H , ∆ oxime with hydroxyl amine. Compound will be -
(3)  → (4)  →
⊕
(ii)H (1) CH2=CH—CH2—OH
(2) CH3CH2CHO
HD0040
(3) CH2=CH—O—CH3
40. Formaldehyde reacts with conc. alkali to form :- (4) CH3COCH3
CC0048
(1) A resinous mass
(2) Formic acid 47. Aldehyde and ketone are distinguished by
reagent
(3) A mixture of methanol and sodium formate (1) Fehling solution (2) H2SO4
(4) Methanol (3) NaHSO3 (4) NH3
CC0049
CC0041
41. Which of the following compounds does not give 48. Carbonyl group is converted into methylene
group by -
aldol condensation :-
(1) Acidic reduction
(1) CH3CHO (2) CH3CH2CHO
(2) Raney Ni
(3) HCHO (4) CH3CH2CH2CHO (3) Basic hydrolysis
CC0042
(4) Normal Hydrogenation
42. Cannizzaro reaction is given by :-
CC0050
(1) Aldehydes containing α-hydrogen atoms
(2) Aldehydes as well as ketones containing 49. When acetaldol is treated with excess of acid
α-hydrogen atoms then unsaturated product will be :-
(3) Aldehydes not containing α-hydrogen atoms (1) Alcohol (2) Aldehyde
(4) Aldehydes containing β-hydrogen atoms (3) Acid (4) Alkyl halide
CC0043 CC0051

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50. The reagent used for the separation of O O 
OH/∆
acetaldehyde from acetophenone is - 54. H–C–CH2CH2CH2CH2–C–H

(1) NaHSO3 (2) C6H5NHNH2 Product (A) is :-

(3) NH2OH (4) NaOH + I2 O=C–CH3
CC0052
(1)
51. The most suitable reagent for the conversion of
CH=O
RCH2OH → RCHO (2)

(1) KMnO4
CH2–CH2CH2CH2CH2–COOH
(2) K2Cr2O7 (3)
OH
(3) CrO3/H2SO4
CH2–CH2CH2CH2CH2–CH2

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(4) PCC (Pyridinium chloro chromate) (4)
OH OH
CC0053
CC0057
52. The major organic product formed from the 55. Which of the following reaction will not give
following reaction is :– ketone?
R – COCl
(1) R – MgX + 
O 
→
(i) CH3NH2 +
(ii) LiAlH4 (iii) H2O H3O
(2) R – CN + R – MgX →  
→
anhy. AlCl3
NHCH3 (3) + RCOCl
NHCH3
(1) (2) CS2 H2O+
OH (4) CH3 + CrO2Cl2

NHCH3 NHCH3 CC0209

56. Select the incorrect option :
(3) (4)
OH OCH3 Conversion Reagent
CC0054 (1) Hexan-1-ol→ hexanal C5H5NH+CrO3Cl–
O (2) Ethanenitrile→ Ethanal DIBAL–H

H / H2 O ⊕ (3) p-fluorotoluene, → K2Cr2O7, H+

53. + CH3MgBr  → P 
HBr
→Q
p-fluorobenzaldehyde
Mg
 → R →
HCHO
S, S is : (4) But-2-ene → Ethanal O3,H2O-Zn dust
Ether H⊕ / H O
CC0210
2

OH 57. True statement about acetone is

OH
(1) (2) (1) α–H of acetone is acidic due to strong
electron withdrawing carbonyl group
(2) α–H of acetone is acidic due to resonance
(3) OH (4) OH stabilisation of conjugate base
(3) It gives β-Hydroxy ketone with dilute alkali
CC0056
(4) All
CC0211

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2 Cl 62. The correct increasing order of carbonyl
58. CH3CH3  → (A)
Aq.KOH PCC
→ (B)  → (C)
hν compounds towards nucleophilic addition

OH reaction.
(D)
∆ (1) Butanone < Propanone < Propanal < Ethanal
The product D is :- (2) Butanone < Propanal < Propanone < Ethanal
(1) CH2 = CH2 (3) Butanone < Ethanal < Propanone < Propanal
(2) CH3–CH–CH2–CHO
(4) Butanone < Ethanal < Propanal < Propanone
OH CC0216
(3) CH3–C–CH3
63. Which of the following carbonyl group give the
O positive fehling test ?
(4) CH3–CH=CH–CHO (1) Aliphatic aldehydes (2) Aromatic aldehydes
CC0212 (3) Ketones (4) Both (1) and (2)
59. Select the correct statement for C=O and C=C
PO0217
bond.

®
(1) Carbon–Oxygen double bond is polar but CARBOXYLIC ACID
carbon-carbon double bond is non-polar
64. When propanoic acid is treated with aqueous
(2) Carbon–Oxygen bond length is 123 pm than
sodium bicarbonate, CO2 is liberated. The C of
that of carbon-carbon bond length is 134 pm
CO2 comes from :-
(3) Carbonyl compounds undergo nucleophilic
(1) methyl group
addition reaction but compounds containing
ethylenic double bonds undergo electrophilic (2) carboxylic acid group
addition reaction (3) methylene group
(4) All of these (4) bicarbonate
CC0213 PO0060
60. Select the structure of chromium complex formed 65. In a set of reactions acetic acid yielded a
by the reaction of toluene with chromylchloride product D
followed by hydrolysis to give benzaldehyde and SOCl Benzene
2
also the name of the reaction. CH3COOH → A 
→ B
Anhy.AlCl3

CH(OCrCl2)2 H O⊕
NaCN 3
(1) and Etard reaction  → C →D
The structure of D would be –
CH(OCrOHCl2)2 OH
(2) and Etard reaction
C—COOH
(1)
CH2(OCrOHCl2) CH3
(3) and Rosenmund reaction
COOH

CH(OCrOH2Cl)2 CH2–C–CH3
(2)
(4) and Rosenmund reaction
OH
CC0214 CN
61. The methanal, ethanal and propanone are
C–CH3
miscible with water because they form (3)
(1) Vander waal's forces with water OH

(2) H-bond with water OH

(3) dipole-dipole bond with water CH2–C–CH3

(4)
(4) ion-dipole bond with water CN
CC0215
CA0061

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ACID DERIVATIVE 69. Which of the following reagents may be used to
distinguish between phenol and benzoic acid ?
66. The compounds A and B in the reaction
(1) Victor-Mayer test
sequence
(2) Neutral FeCl3
Phenol CH3COONa
B CH3COCl → A (3) Aqueous NaOH
(4) Tollen's reagent
are given by the set respectively :-
PO0066
(1) CH3CO–O–COCH3, C6H5CH2OH
70. Acyl chlorides undergo :-
(2) CH3CO–O–COCH3, C6H5OCOCH3 (1) Nucleophilic addition reactions
(3) CH3COCH3, C6H5OCOCH3 (2) Nucleophilic substitution reactions
(3) Electrophilic substitution reactions
(4) CH3–C–O–O–C–CH3 , CH3–C–O–C6H5 (4) Electrophilic addition reactions

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O O O CA0067
CA0062 71. The reaction of ethanol on acetic anhydride is an
Re d P / Cl2 example of :-
67. CH3–CH2–COOH  → A 
Alc.
KOH
→ B
(1) Nucleophilic addition
structure of B is :-
(2) Nucleophilic substitution
(1) CH2=CH–COOH
(3) Electrophilic addition
(2) CH3–CH–COOH (4) Free radical substitution
Cl CA0068

(3) CH2–CH2–COOH 72. The reduction of acetamide gives :-

Cl (1) CH3CH2NH2

O (2) (CH3)2CHNH2

(4) CH3–CH2–C–Cl (3) (CH3)3CNH2

CA0063 (4) (CH3CH2)2NH

CA0069
68. Which is most reactive towards hydrolysis.
73. Which is used in preparation of aldehyde by
(1) CH3 C–NH–CH3 rosenmund reduction
O (1) Ester (2) Acid

(2) O2N C–NH–CH3 (3) Acid halide (4) Alcohol

O CC0070

P2O5
(3) Cl C–NH–CH3 74. CH3–C–NH2 →
∆ ?
O O

(4) C–NH–CH3 (1) CH3COOH (2) CH3–CN

O (3) CH3–CH3 (4) CH3–CHO

CA0065 CA0072

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CHO
NaOH H⊕ ?
75. A
∆
CHO

CH2OH
O
(1) (2)
COOH
O

(3) (4)
O O

CC0073

EXERCISE-I (Conceptual Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 3 1 3 3 3 1 4 3 4 4 4 4 3 3 2
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 3 4 2 4 1 2 4 3 4 2 4 2 2 3 2
Que. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans. 4 1 1 3 4 2 3 3 3 3 3 3 2 3 3
Que. 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Ans. 4 1 1 2 1 4 2 2 2 4 3 4 4 4 2
Que. 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75
Ans. 2 1 1 4 1 2 1 2 2 2 2 1 3 2 2

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EXERCISE-II (Previous Year Questions) AIPMT/NEET
AIPMT 2007 CH3 CH3
1. Consider the following compounds: C—C
(1)
(i) COCl OH OH

(2) CH – CH
(ii) O2N COCl
OH OH

(iii) H3C COCl C = CH – C

(3)
CH3 O
(iv) OHC COCl
(4) CH – CH2 – C
The correct order of reactivity towards hydrolysis

®
CH3 O
is:-
CC0079
(1) (i) > (ii) > (iii) > (iv)
(2) (iv) > (ii) > (i) > (iii) 5. A strong base can abstract an α- hydrogen from

(3) (ii) > (iv) > (i) > (iii) (1) Ketone (2) Alkane
(3) Alkene (4) Amine
(4) (ii) > (iv) > (iii) > (i)
CC0080
CA0075
2. Which one of the following on treatment with AIPMT 2009
50% aq. NaOH yields the corresponding alcohol 6. H2COH.CH2OH on heating with periodic acid
and acid
gives :-
(1) C6H5CHO H
(1) 2 C=O (2) 2CO2
(2) CH3CH2CH2CHO H
(3) CH3COCH3 CHO
(3) 2HCOOH (4)
(4) CH3CHO
CHO
CC0076
AE0081
3. The product formed in aldol reaction is :-
7. Consider the following reaction,
(1) a β–hydroxy aldehyde or ketone
PBr 3 alc. KOH
(2) an α–hydroxy aldehyde or ketone ethanol → X  → Y

(3) an α, β–unsaturated ester ( i ) H2 SO4 room temperature

 → Z;
( ii ) H2O
(4) a β–hydroxy acid
the product Z is :-
CC0078
(1) CH3CH2OH
(2) CH2 = CH2
AIPMT 2008
(3) CH3CH2 – O – CH2 – CH3
4. Acetophenone when reacted with a base,
C2H5ONa, yields a stable compound which has (4) CH3 – CH2 – O – SO3H
the structure :- AE0082

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8. Propionic acid with Br2/P yields a dibromo AIPMT 2010
product. Its structure would be :- 11. Which of the following reactions will not result in
Br
the formation of carbon-carbon bonds ?
(1) CH3–C–COOH (1) Friedel-Crafts acylation
Br (2) Reimer-Tieman reaction
(2) CH2Br – CHBr – COOH (3) Cannizaro reaction
Br
(4) Wurtz reaction
(3) H–C–CH2COOH CC0086
Br 12. When glycerol is treated with excess of HI, it
(4) CH2Br – CH2 – COBr produces :-
CA0083
(1) allyl iodide

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9. Consider the following reaction :
(2) propene
CH3Cl KMnO4
Phenol Zn dust X Y Z (3) glyceryl triiodide
∆ Anhydrous ∆
AlCl3 (4) 2-iodopropane
the product Z is :- AE0087
(1) Benzene (2) Toluene 13. Match the compounds given in List–I with their
(3) Benzaldehyde (4) Benzoic acid
characteristic reactions given in List–II. Select the
AH0084
correct option.
10. In a set of reactions, ethyl benzene yielded a
List–I (Compounds)
product D
(a) CH3CH2CH2CH2NH2
CH2CH3
KMnO4 Br2 C2H5OH (b) CH3C≡CH
B C + D
KOH FeCl3 H (c) CH3CH2COOCH3
'D' would be :- (d) CH3CH(OH)CH3
COOC2H5
List–II (Reactions)

(1) (i) Alkaline hydrolysis

Br (ii) With KOH (alcohol) and CHCl3 produces bad
CH2–CH–COOC2H5 smell
(2) Br (iii) Gives white ppt. with ammonical AgNO3

Br (iv) With Lucas reagent cloudiness appears after

5 minutes
(3) Options :
Br
CH2COOC2H5 (a) (b) (c) (d)
(1) (iii) (ii) (i) (iv)
COOH
(2) (ii) (iii) (i) (iv)
(4) (3) (iv) (ii) (iii) (i)
OCH2CH3
(4) (ii) (i) (iv) (iii)
AH0085 PO0088

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AIPMT Pre. 2011 AIPMT Mains 2011
14. In the following reactions,
17. An organic compound 'A' on treatment with NH3
CH3
+
gives 'B' which on heating gives 'C'. 'C' when
H /Heat
(a) CH3–CH–CH–CH3 A B
Major + Minor treated with Br2 in the presence of KOH
product product
OH produces ethylamine. Compound 'A' is :-
HBr, dark
(b) A in absence of peroxide
C D
Major + Minor (1) CH3CH2COOH
product produc

the major products (A) and (C) are respectively :- (2) CH3COOH
CH3 CH3 (3) CH3CH2CH2COOH
(1) CH2=C–CH2–CH3 and CH2–CH–CH2–CH3 (4) CH3–CHCOOH

CH3
Br
CH3 CA0094
CH3
(2) CH3–C=CH–CH3 and CH3–C–CH2–CH3 18. Match the compounds given in List-I with List-II

®
and select the suitable option using the code
Br
given below.
CH3 CH3
(3) CH3–C=CH–CH3 and CH3–CH–CH–CH3 List-I List-II

Br (a) Benzaldehyde (i) Phenolphthalein

CH3 CH3 (b) Phthalic anhydride (ii) Benzoin

(4) CH2=C–CH2–CH3 and CH3–C–CH2–CH3 condensation

Br (c) Phenyl benzoate (iii) Oil of wintergreen

AE0091 (d) Methyl salicylate (iv) Fries rearrangement

15. In a set of reactions m-bromobenzoic acid gave a Code :

product D. Identify the product D
COOH (a) (b) (c) (d)
SOCl2 NH3 NaOH (1) (ii) (i) (iv) (iii)
B C D
Br2
Br (2) (iv) (i) (iii) (ii)
A
(3) (iv) (ii) (iii) (i)
SO2NH2 COOH
(4) (ii) (iii) (iv) (i)
(1) (2) CA0095
Br Br
NH2 CONH2 AIPMT Pre. 2012

19. In the following sequence of reactions

(3) (4) +
LiAlH4
Br Br KCN
CH3 – Br  → A H3 O
→ B
ether
→ C,
CA0092 the end product (C) is:
16. Clemmensen reduction of a ketone is carried out (1) Acetaldehyde
in the presence of which of the following ? (2) Ethyl alcohol
(1) Glycol with KOH
(3) Acetone
(2) Zn-Hg with HCl
(3) LiAlH4 (4) Methane
(4) H2 and Pt as catalyst
CA0097
CC0093

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20. Predict the products in the given reaction. NEET UG 2013

CHO 23. Reaction by which Benzaldehyde cannot be

prepared :-
50% KOH COOH
Cl (1) + Zn/Hg and conc. HCl

CH3
CH2OH COO¯ K⊕
(1) + (2) + CrO2Cl2 in CS2

Cl Cl followed by H3O⊕
COCl
CH2OH COO¯ K⊕ (3) + H2 in presence
(2) +
of Pd+BaSO4
OH OH
(4) + CO+HCl in presence

®
CH2OH CH2COO¯ K⊕
(3) + of anhydrous AlCl3
CC0101
Cl Cl
AIPMT 2014
CH2OH OH K⊕ 24. Among the following sets of reactants which one
(4) +
produces anisole?
OH OH (1) CH3CHO ; RMgX
CC0098 (2) C6H5OH ; NaOH ; CH3I
(3) C6H5OH ; neutral FeCl3
21. CH3CHO and C6H5CH2CHO can be
(4) C6H5 – CH3 ; CH3COCl; AlCl3
distinguished chemically by :
AE0105
(1) Tollen's reagent test
25. Which of the following will not be soluble in
(2) Fehling solution test sodium hydrogen carbonate?
(3) Benedict test (1) 2, 4, 6-trinitrophenol
(4) Iodoform test (2) Benzoic acid
HD0099 (3) o-Nitrophenol

AIPMT Mains 2012 (4) Benzenesulphonic acid

PO0106
22. Consider the following reaction :
AIPMT 2015
COCl
H2
‘A’ 26. An organic compound 'X' having molecular
Pd-BaSO4
formula C5H10O yields phenyl hydrazone and
The product 'A' is : gives negative response to the Iodoform test and
Tollen's test. It produces n-pentane on reduction.
(1) C6H5COCH3 (2) C6H5Cl
'X' could be :-
(3) C6H5CHO (4) C6H5OH (1) 2-pentanone (2) 3-pentanone
(3) n-amyl alcohol (4) pentanal
CA0100
CC0108
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RE-AIPMT 2015 30. Identify A and predict the type of reaction

27. Reaction of phenol with chloroform in presence

OCH3
of dilute sodium hydroxide finally introduces NaNH2
A
which one of the following functional group ? Br

(1) –CHCl2 (2) –CHO OCH3

NH2
(3) –CH2Cl (4) –COOH
(1) and elimination addition
AH0109
reaction

NEET-II 2016 OCH3

28. The correct structure of the product A formed Br
(2) and cine substitution reaction

®
in the reaction

O OCH3
H2(gas, 1 atmpsphere)
A is :- (3) and cine substituion reaction
Pd/carbon, ethanol

OH OCH3

(1) (4) and substitution reaction

NH2
OH HD0121
⊕
(2) 31. Of the following, which is the product formed
when cyclohexanone undergoes aldol
OH condensation followed by heating ?

(3)
(1)

O O

(4)
(2)

CC0113 OH

NEET(UG) 2017 (3)

29. The heating of phenyl–methyl ethers with HI O O

produces O
(1) iodobenzene (2) phenol
(4)
(3) benzene (4) ethyl chlorides
OH
AE0120
CC0122

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32. Consider the reactions :-
(3) CH–CH3 and I2
Cu/573K [Ag(NH3)2] OH/∆
X A Silver mirror
observed OH
(C2H6O) OH/∆
O Y
CH3
NH2–NH–C–NH2
Z
(4) CH3 OH and I2
Identify A, X, Y and Z
HD0133
(1) A-Methoxymethane, X-Ethanol, Y-Ethanoic
acid, Z-Semicarbazide. 35. The compound A on treatment with Na gives B,
(2) A-Ethanal, X-Ethanol, and with PCl5 gives C. B and C react together to

Y-But-2-enal, Z-Semicarbazone give diethyl ether. A, B and C are in the order

®
(3) A-Ethanol, X-Acetaldehyde, (1) C2H5OH, C2H6, C2H5Cl

Y-Butanone, Z-Hydrazone (2) C2H5OH, C2H5Cl, C2H5ONa

(4) A-Methoxymethane, X-Ethanoic acid,
(3) C2H5Cl, C2H6, C2H5OH
Y-Acetate ion, Z-hydrazine
(4) C2H5OH, C2H5ONa, C2H5Cl
CC0123
AE0134
NEET(UG) 2018
33. Carboxylic acid have higher boiling points than 36. Identify the major products P, Q and R in the

aldehydes, ketones and even alcohols of following sequence of reaction :

comparable molecular mass. It is due to their Anhydrous
AlCl3 (i) O2
(1) formation of intramolecular H-bonding + CH3CH2CH2Cl P + Q+R
(ii) H3O /∆
(2) formation of carboxylate ion
CH2CH2CH3 CHO
(3) more extensive association of carboxylic acid
via van der Waals force of attraction (1) , , CH3CH2–OH
(4) formation of intermolecular H-bonding. P Q R
CC0132
CH2CH2CH3 CHO COOH

34. Compound A, C8H10O, is found to react with (2) , ,

NaOI (produced by reacting Y with NaOH) and
P Q R
yields a yellow precipitate with characteristic
smell. CH(CH3)2 OH
(3) , , CH3CH(OH)CH3
A and Y are respectively
P Q R
(1) H3C CH2–OH and I2
OH
CH(CH3)2
(4) , , CH3–CO–CH3
(2) CH2–CH2–OH and I2
P Q R
AH0135

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NEET(UG) 2019 CH2OH
PCC
37. The structure of intermediate A in the following (3)  →
(Pyridinium
chlorochromate)

reaction is :-
CH2OH
CH3 KMnO / H+
(4) 
4
→
CH OH O
CH3
O2 H+
A + H3C CH3 CA0219
H2O

39. When vapours of a secondary alcohol is passed

CH3
over heated copper at 573 K, the product
CH
O formed is :-
CH3

®
(1) (1) a carboxylic acid (2) an aldehyde

(3) a ketone (4) an alkene

CH3
CC0220
H3C–C–O–O–H

40. The major products C and D formed in the

(2)
following reactions respectively are :-
CH3
excess HI
H3C–CH2–CH2–O–C(CH3)3 
∆
→C + D
O O CH

CH3 (1) H3C–CH2–CH2–I and I–C(CH3)3

(3)

(2) H3C–CH2–CH2–OH and I–C(CH3)3

CH2–O–O–H
HC (3) H3C–CH2–CH2–I and HO–C(CH3)3
CH3
(4) (4) H3C–CH2–CH2–OH and HO–C(CH3)3

AE0221
AE0218

NEET(UG) 2019 (ODISHA)

NEET(UG) 2020
38. The reaction that does not give benzoic acid as 41. Reaction between benzaldehyde and

the major product is :- acetophenone in presence of dilute NaOH is

known as :
CH2OH
K Cr O (1) Cross Aldol condensation
(1) 
2 2 7
→
(2) Aldol condensation
COCH3 (3) Cannizzaro's reaction
(i) NaOCl
(2)  →
(ii) H3 O+ (4) Cross Cannizzaro's reaction

CC0237

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NEET(UG) 2020 (COVID-19) 45. The product formed in the following chemical
42. Which of the following acid will form an (a) reaction is

Anhydride on heating and (b) Acid imide on O

O
strong heating with ammonia ? CH2–C–OCH3
NaBH4
?
COOH C2H5OH
CH3
(1)
H
COOH OH
CH2–C–OCH3
COOH (1)
OH
CH3
(2)
O
COOH CH2–CH2–OH
COOH (2)
CH3

®
(3) H
OH
CH2–C–CH3
COOH
(3) OH
OH CH3
O
(4) OH
CH2–C–OCH3
COOH (4)
CA0238 CH3
CC0241
43. Identify compound (A) in the following reaction :
46. Match List-I with List-II.
CHO List-I List-II
H2/Pd/BaSO4
A CO, HCl
(a) (i) Hell-Volhard-
Anhyd.AlCl3/CuCl

(1) Benzoyl chloride Zelilnsky reaction

(2) Toluene Gattermann-Koch

(b) O (ii) Reaction
(3) Acetophenone R–C–CH3+ NaOX→

(4) Benzoic acid (c) R–CH2–OH + R'COOH (iii) Haloform

CC0239 Conc. H2 SO4
NEET(UG) 2021 
→ reaction
(d) R–CH2–COOH (iv) Esterification
44. What is the IUPAC name of the organic
compound formed in the following chemical (i ) X 2 /Re d P
 (ii ) H2O
→
reaction ?
Choose the correct answer from the options
(i ) C2 H5 MgBr, dry Ether
Acetone  (ii ) H O, H +
→ Product
given below.
2

(1) 2-methyl propan-2-ol (1) (a)-(iv), (b)-(i), (c)-(ii), (d)-(iii)

(2) pentan-2-ol (2) (a)-(iii), (b)-(ii), (c)-(i), (d)-(iv)
(3) pentan-3-ol (3) (a)-(i), (b)-(iv), (c)-(iii), (d)-(ii)
(4) 2-methyl butan-2-ol (4) (a)-(ii), (b)-(iii), (c)-(iv), (d)-(i)
CC0240 CA0242
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47. The intermediate compound ‘X’ in the following In the light of the above statements, choose the
chemical reaction is : most appropriate answer from the options given
below:
O
CH3 C (1) Both Statement I and Statement II are
+ CrO2Cl2 CS2 H3O+ H
X incorrect.

(2) Statement I is correct but Statement II is

CH(OCrOHCl2)2
incorrect.
(1)
(3) Statement I is incorrect but Statement II is
CH(OCOCH3)2 correct
(2)
(4) Both Statement I and Statement II are

Cl correct

®
CH
Cl
AE0245
(3)
50. Given below are two statements : -
Cl
CH Statement I :
H
(4)
The boiling points of aldehydes and ketones are
CC0243 higher than hydrocarbons of comparable
NEET (UG) 2021(Paper-2) molecular masses because of weak molecular
48. Which of the following reactions is not possible?
association in aldehydes and ketones due to
(1) HC ≡ CH + NaOH → HC ≡ CNa + H2O dipole - dipole interactions.

Statements II :
(2) + HCl Cl
The boiling points aldehydes and ketones are

(3) C2H5OH + NaCl → C2H5Cl lower than the alcohols of similar molecular
masses due to the absence of H-bonding.
(4) All of the these
In the light of the statements, choose the most
HC0244
appropriate answer from the options given
NEET(UG) 2022
below:
49. Given below are two statements :
Statement I: (1) Both statements I and statements II are
In Lucas test, primary, secondary and tertiary incorrect.
alcohols are distinguished on the basis of their
(2) Statement I is correct but statements II is
reactivity with cone. HCl + ZnCl2, known as
incorrect
Lucas Reagent.
(3) Statements I is incorrect but statements II is
Statement II:
Primary alcohols are most reactive and correct.

immediately produce turbidity at room (4) Both statements I and statements Ii are
temperature on reaction with Lucas Reagent. correct.

CC0246

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51. Match List-I with List -II. NEET(UG) 2022 (Overseas)
List-I List-II 53. Given below are two statements :
(Products formed) (Reaction of carbonyl Statement - I : The product of reaction of
compound with) phenol with bromine depends on the nature of

(a) Cyanohydrin (i) NH2OH solvent.

Statement - II : Reaction of phenol with
(b) Acetal (ii) RNH2 bromine in CHCI3 gives monosubstituted bromo
derivative whereas reaction of phenol with
(c) Schiff's base (iii) alcohol
bromine water yields trisubstituted bromo
(d) Oxime (iv) HCN derivative of phenol.
In light of the above statements, choose the most
Choose the correct answer from the options
appropriate answer from the options given

®
given below : below:
(1) Statement-I is incorrect and Statement-II
(1) (a)-(ii), (b) - (iii), (c) - (iv), (d)- (i)
is correct
(2) (a)-(i), (b) - (iii), (c) - (ii), (d)- (iv) (2) Both Statement-I and Statement–II are
correct
(3) (a)-(iv), (b) - (iii), (c) - (ii), (d)- (i)
(3) Both Statement-I and Statement–II are

(4) (a) -(iii), (b) - (iv), (c) - (ii), (d)- (i) incorrect
(4) Statement-I is correct and Statement-II is
CC0247 incorrect
52. Which one of the following is not formed when
AE0249
acetone reacts with 2-pentanone in the presence 54. The major products formed in the following
reaction are
of dilute NaOH followed by heating ?
H3C
CH3 O
H3C H3C + HI → ?
CH3 CH3
(1) H3C
O CH3
H3C
(1) CH2, CH3I
CH3 O
(2) H3C
CH3 CH3
H3C
(2) H C I, CH3–OH
CH3 3

H3C
CH3
CH3 H3C
(3)
CH3 O (3) H C OH, CH3–OH
3

H3C
O CH3 H3C
(4) (4) H C
3 OH, CH3–I
H3C CH3 H3C
AE0250
CC0248

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55. Given below are two statements : Re-NEET(UG) 2022
57. Match the reagents (List-I) with the product
Statement-I : Aldehydes and ketones having at
(List-II) obtained from phenol.
List-I List-II
least one α-hydrogen undergo aldol
(a) (i) NaOH (i) Benzoquinone
condensation in the presence of dilute alkali as (ii) CO2
(iii) H+
catalyst. (b) (i) Aqueous (ii) Benzene
NaOH + CHCl3
Statement-II : When aldol condensation is (ii) H+
(c) Zn duct, ∆ (iii) Salicyl
carried out between two different aldehydes, it is aldehyde
called cross aldol condensation. Ketones do not (d) Na2Cr2O7, H2SO4 (iv) Salicylic acid
Choose the correct answer from the options
give this reaction. given below :

®
(1) (a) – (iii), (b) – (iv), (c) – (i), (d) – (ii)
In light of the above statements, choose the most (2) (a) – (ii), (b) – (i), (c) – (iv), (d) – (iii)
appropriate answer from the options given (3) (a) – (iv), (b) – (iii), (c) – (ii), (d) – (i)
(4) (a) – (iv), (b) – (ii), (c) – (i), (d) – (iii)
below:
AE0253
(1) Statement-I is incorrect and Statement-II
58. The incorrect method to synthesize benzaldehyde is:
is correct. O
(2) Both Statement-I and Statement-II are
(1) Cl, H2, Pd-BaSO4
correct.
(3) Both Statement-I and Statement-II are O
incorrect.
(2) OC2H5, DIBAL-H,
(4) Statement-I is correct and Statement-II is followed by H2O
incorrect.
CH3
CC0251
(3) , CrO2Cl2,
56. The product(s) formed from the following +
followed by H3O in CS2
reaction is/are
CN
CrO3, H2SO4
(4) , CH3MgBr,
R–CH2–C–CH2–R ? +
High Temperature followed by H3O
O
CC0254
59. Which one of the following reaction sequence is
(1) RCH2COOH only
incorrect method to prepare phenol ?
(2) R–CH2–CH–CH2–R only (1) Aniline, NaNO2 + HCl, H2O, heating
(2) Cumene, O2, H3O+
COOH
Cl
(3) , NaOH, STP condition
(3) RCOOH and RCH2COOH

(4) RCOOH only (4) +

, oleum, NaOH, H3O
CC0252 AE0255

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60. The product formed from the following reaction
sequence is :

O +
(i) HCN, (ii) H3O
H
(iii) NaOH and CaO, ∆
(3 : 1)

COOH OH
(1) (2)

O O
OH NH2
(3) (4)

®
CC0256

EXERCISE-II (Previous Year Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 3 1 1 3 1 1 1 1 4 1 3 4 2 2 3
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 2 1 1 2 1 4 3 1 2 3 2 2 4 2 4
Que. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans. 1 2 4 3 4 4 2 3 3 1 1 1 1 4 4
Que. 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Ans. 4 1 4 2 4 3 1 2 2 3 3 3 4 3 2

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EXERCISE-III (Analytical Questions) Master Your Understanding
1. Methanol can be distinguished from ethanol by 5. The structures of the compounds / ions A, B
the following except and C in the reaction sequence are given by
(1) Reaction with iodine and alkali the set :-
(2) Reaction with salicylic acid and H2SO4 Cl
HCl
(3) Reaction with Lucas reagent B
2OH
A
(4) Boiling point 360° CH3I
C
AE0147

2. Ethanol on heating with acetic acid in the (1) OH, Cl, CH3
presence of a few drops of sulphuric acid gives
the smell of O, OH, OCH3
(2)
(1) Oil of wintergreen

®
(2) Oil of mustard
O, Cl, I
(3) An ester (3)

(4) Oil of bitter almonds

(4) O, OH, I
CA0148

3. The compounds A, B and C in the reaction HD0151

sequence are given by the set :-
PCl5 Zn
6. A OH B
HBr
CH3CH2OH  Mg Distil
∆ → A  → B

(i) CH CHO
NaOH CH3COCl

3
⊕
→ C
(ii) H3 O
C
(1) CH3CH2Br, CH3CH2MgBr, (CH3)3C—OH The compounds A, B and C in the above reaction
(2) CH3CH2Br, (CH3CH2)2Mg,(CH3)2CHCH2OH sequence are :-
(1) Chlorobenzene, benzene, methyl benzoate
(3)CH3CH2Br,CH3CH2MgBr,CH3CH(OH)CH2CH3
(2)Triphenyl phosphate, benzene, phenyl acetate
(4) CH3CHBr2,CH3CH(MgBr)2,CH3CH(OH)CH3
(3) Benzyl chloride, benzene, phenyl acetate
AE0149 (4)Benzyl chloride, benzene, phenylacetyl chloride
4. Which of the following reactions will not lead to AE0152
a phenol :-
7. In the reaction sequence —
(1) C6H5SO3Na + NaOH →
i) Fuse / ∆
ii) H +
NaOH CH3I
SO3Na A B HI C+D
(2) C6H5N2Cl + H2O 
→ Boil 350°C

NaOH A, B, C and D are given by the set :-

(3) C6H5ONa + RX 
Heat

→
(1) Sodium phenate, anisole, C6H5I, CH3OH
OH
(4) Heat
+ NaOH(CaO)  → (2) Sodium phenate, phenetole, C2H5I, C6H5OH
COONa (3) Sodium phenate, anisole, C6H5OH, CH3I
HD0150 (4) Sodium phenate, phenetole, C6H5I, C2H5OH
HD0153

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8. Compound A and C in the following reaction are 12. The compounds A, B and C in the reaction
Hydroboration sequence
(i) CH3MgBr H2SO4 oxidation
CH3CHO (A) (B) (C) CH3 I2 Ag dil. H2SO4
(ii) H2O ∆ C=O A ∆ B C
CH3 Alkali Hg+2
(1) Identical
are given by the set :-
(2) Functional isomer
(3) Positional isomer (1) CHI3, H2C=CH2, CH3CH2–OH

(4) Optical isomer (2) CHI3, HC≡CH, CH3CHO

CC0154 (3) CHI3, CH3–C≡CH, CH3COCH3

9. Which of the following aldehydes does not form O

iodoform on heating with iodine and alkali ? (4) CHI3, CH3–CH–CH3 , CH3–C–CH3
(1) CH3–C–C–H OH

®
O O HD0159
(2) ICH2CHO 13. In the reaction sequence
(3) CH3–CH2–CHO Pd + BaSO4 H3 O ⊕
RCOCl + H
2
HCN
→ A → B → C
O
A,B and C are given by the set :-
(4) CH3–CH–C–H
(1) RCHO, RCH(OH)CN, RCH(OH)CH2NH2
OH
(2) RCHO, RCH(OH)CN, RCH(OH)COOH
HD0155
(3) RCHO, R C CH2 , R–C–CH –C–OH
2
10. A carbonyl compound gives a positive iodoform
O CN O O
test but does not reduce Tollen's reagent or
Fehling's solution. It forms a cyanohydrin with (4) RCHO, R–CH2–CN, R–CH2–COOH
HCN, which on hydrolysis gives a hydroxy acid CA0160
with a methyl side chain. The compound is ?
14. In the reaction sequence
(1) Acetaldehyde
(2) Propionaldehyde dil H2SO4.Hg⊕2 CHCl3
CH3–C≡CH A B
(3) Acetone
I2 NaOH
(4) Crotonaldehyde
C
CC0157
A, B and C are given by the set :-
11. Which of the following statement is wrong :-
(1) CH3CH2CHO, CH3CH2CH2Cl, CHI3
(1) All methyl ketones give a positive iodoform
(2) CH3COCH3,CCl3–C–CH3 , CHI3
test
O
(2) Acetaldehyde is the only aldehyde that gives
iodoform test (3) CH3COCH3, CCl3–C(CH3)2 ,CHI3

(3) All secondary alcohols give positive iodoform OH

test
(4) CH3CH2CHO, CCl3–CH–CH2–CH3 , CHI3
(4) Any alcohol that can be oxidised to an acetyl
OH
group gives a positive iodoform test
HD0158 CC0161

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15. The reagents A and B in the reaction sequence 20. CH3CHO and CH3COCH3 can not be
A
CH3COOC2H5 → CH3COOC(CH3)3 distinguished by :-
B
CH3CONHNH2 (1) Fehling solution
(2) Grignard reagent
are given by the set :-
(1) CH3–CH–OH , H2N–NH2 (3) Schiff's reagent
CH3 (4) Tollen's reagent
(2) CH3–CH–OH , H2N–OH PO0168
⊕
H O NH
CH3 21. CH3CH2CH2–C≡N 
3

→ A 
∆
3
→B
CH3 Product 'B' is :-
(3) CH3–C–OH , H2N–NH2 (1) CH3–CH2CH2–C–OH
CH3 O
CH3 (2) CH3CH2CH2–C–H

®
(4) CH3–C–OH , H2N–OH O
CH3 (3) CH3CH2CH2–NC
CA0163 (4) CH3CH2CH2–C–NH2
16. Methyl amine reacts with acetyl chloride and
O
forms :-
(1) CH3NH2 (2) CH3NHNa CA0170
(3) CH3NHCOCH3 (4) (CH3)2NCOCH3 22. Sodium ethoxide has reacted with ethanoyl
CA0164
chloride. The compound that is produced in the
17. Intermediates formed during reaction of
above reaction is :-
R–C–NH2 with Br2 and KOH are:
(1) Ethyl chloride
O
(1) RCONHBr and RNCO (2) Ethyl ethanoate
(2) RNHCOBr and RNCO (3) Diethyl ether
(3) RNH—Br and RCONHBr
(4) 2–Butanone
(4) RCONBr2
AM0165 CA0171
NaCN Ni/H2 Acetic
18. CH3CH2Cl  → X → Y
anhydride
→ Z
23. Sodium phenoxide when heated with CO2 under
Z in the above reaction sequence is :– pressure at 125°C yields a product which on
(1) CH3CH2CH2NHCOCH3 acetylation produces C
(2) CH3CH2CH2NH2
(3) CH3CH2CH2CONHCH3 ONa 125°C H
+

+CO2 5 atm.
B Ac2O
C
(4) CH3CH2CH2CONHCOCH3
CA0166 The major product C would be :
19. In a set of the given reactions, acetic acid yielded
OCOCH3
a product C. OH
PCl5
CH3COOH  C6 H6
→ A  COOCH3
AlCl3 →
B (1) (2)
C2 H5 MgBr / H3 O⊕
COOH

→ C product C would be:-
ether

(1) CH3CH(OH)C2H5 (2) CH3COC6H5 OH

OCOCH3
C2H5 COOH
COOH
(3) (4)
(3) CH3CH(OH)C6H5 (4) CH3–C(OH)C6H5
CA0167 COCH3

AE0175
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
® Chemistry : Oxygen Containing Compound
Pre-Medical
24. Which of the following reaction sequence does 27.Select the correct option for the following
reaction:
not give phenol ? SO3H H+ transfer SO3Na
C=O+NaHSO3 C C
Cl NaOH, 623K ONa OH
(1) HCl
300 atm
(1) The position of equilibrium is on RHS for
(2) oleum 1.NaOH, ∆ most ketones
2.H+ (2) The position of equilibrium is on LHS for
most aldehydes
NH2 (3) The hydrogen sulphite addition compound is
(3) NaNO2 H3PO2
HCl H2O
water insoluble
(4) Sulphite addition compounds are useful for
separation and purification of aldehydes
(4) O2 H+ CC0225
H2 O
28. Select the correct option about Fehling's test :

®
AE0222 (1) Fehling test is given by all aldehydes but not
by ketones
25. Which of the following reactions does not give (2) A red brown ppt. of CuO confirms the test
aldehyde as major product ? (3) Fehling solution 'A' is aq. CuSO4
(4) Fehling solution 'B' is alkaline sodium
CrO3. HCl potassium citrate
N PO0226
(1) RCH2OH
29. Correct reactivity order towards nucleophilic
anhy. CrO addition is
(2) RCH2OH 
→ 3

O O
Cu/573K
(3) RCH2OH  →
(a) (b)
KMnO4 , H+ OCH3
(4) RCH2OH →
NO2
CC0223 O
O
26. Which of the following can be used to prepare
(c) (d)
benzaldehyde ? CH3
(1) b > a > d > c (2) a > b > d > c
O (3) b > d > c > a (4) b > d > a > c
H2 CC0227
(I) C – Cl
Pd – BaSO4
30. CH3–CH–CH2–OH is obtained from following
Cl2, hv H2O CH3
(II) CH3
100°C
method
CrO3 (1) CH3–CH2–CH–Cl + H2O
H3O+
(III) CH3
(CH3CO)2O, 0-10°C ∆ CH3
(2) CH3CHO, CH3–CH2MgBr, H2O
CO, HCl (3) H–CHO, CH3–CHMgBr , H2O
(IV)
anhy. AlCl3/CuCl
CH3
(1) I, II (2) II, III, IV (4) CH3–CH–CH2–NH2 + HNO2
(3) I, III, IV (4) I, II, III, IV CH3
CC0224 CC0228

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Chemistry : Oxygen Containing Compound ®
Pre-Medical
31. For the reaction :- 34. Which of the following reagents is/are used in
OH the given reaction ?
Ph–CHO + Ph–C–CH3 293K Major
RCHO → RCOOH
O +
(1) KMnO4/H
The major product is :
CH3 (2) Potassium dichromate
(3) Tollen's reagent
(1) Ph–C–CH2–C–Ph
(4) All of the above
OH O
CC0232

(2) Ph–C–O+Ph–CH2–OH 35. Which of the following statements is/are correct?
O (1) Aldehydes are generally oxidised under
O vigorous conditions
(3) Ph–CH–C–Ph (2) Ketones are easily oxidised to carboxylic acids
OH even under mild oxidising agents

®
O (3) Oxidation of ketones involves carbon-carbon
(4) Ph–CH=CH–C–Ph bond cleavage to give a mixture of carboxylic
CC0229 acids having lesser number of c-atoms than
32. Which of the following substrates gives same the parent ketones.
product on the reduction with DIBAL-H ? (4) All of the above
(1) CH3–(CH2)4–CN and CH3–(CH2)5–COOH CC0233
(2) CH3–(CH2)4–CN and CH3–(CH2)4–COOC2H5 36. Which type of reaction(s) is/are involved in the
(3) CH3–(CH2)4–COOH and CH3–(CH2)4–COCH3 cannizzaro reaction ?
(4) CH3–(CH2)5–COOH and CH3(CH2)4–COOC2H5 (1) Reduction (2) Oxidation
AM0230 (3) Both (1) and (2) (4) None of these
33. Choose the correct alternative from the CC0234
following. 37. The product formed during Hell-volhard-Zelinsky
reaction is :-
(1) Ketones are more reactive than aldehydes
(1) R–CH–COOH
towards NAR.
(2) Aldehydes are more reactive than ketones X
(2) R–CH2–COX
towards NAR.
X
(3) Formaldehyde is the least reactive carbonyl
Compound towards NAR (3) R–C–CH2–COOH
(4) Steric hindrance does not play a role to effect X
the reactivity of carbonyl componds towards (4) R–CH–CH2–COOH
NAR.
X
CC0231 CA0235

EXERCISE-III (Analytical Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 3 3 3 3 2 2 3 3 3 3 3 2 2 3 3
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 3 1 1 4 2 4 2 3 3 4 4 4 3 3 3
Que. 31 32 33 34 35 36 37
Ans. 4 2 2 4 3 3 1

101