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Exercise 1 1683183099
Exercise 1 1683183099
ORGANIC
CHEMISTRY
ENTHUSIAST | LEADER | ACHIEVER
EXERCISE
®
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
®
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?
®
(3) and (1) CH3–CH2–OCH2–CH3
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
(1) CH3–CH–OH 26. Which of the following does not react with aq.
CH NaOH :-
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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
®
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
®
(4) All the above NO2
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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) KMnO4
CH2–CH2CH2CH2CH2–COOH
(2) K2Cr2O7 (3)
OH
(3) CrO3/H2SO4
CH2–CH2CH2CH2CH2–CH2
®
(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
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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
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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
®
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
Cl (1) CH3CH2NH2
O (2) (CH3)2CHNH2
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
O CC0070
P2O5
(3) Cl C–NH–CH3 74. CH3–C–NH2 →
∆ ?
O O
CA0065 CA0072
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CHO
NaOH H⊕ ?
75. A
∆
CHO
CH2OH
O
(1) (2)
COOH
O
(3) (4)
O O
CC0073
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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
®
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
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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
®
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)
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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
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20. Predict the products in the given reaction. NEET UG 2013
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
®
in the reaction
O OCH3
H2(gas, 1 atmpsphere)
A is :- (3) and cine substituion reaction
Pd/carbon, ethanol
OH OCH3
(3)
(1)
O O
(4)
(2)
CC0113 OH
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
®
(3) A-Ethanol, X-Acetaldehyde, (1) C2H5OH, C2H6, C2H5Cl
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Chemistry : Oxygen Containing Compound ®
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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
®
(1) (1) a carboxylic acid (2) an aldehyde
AE0221
AE0218
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
®
(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
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
®
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
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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
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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)
(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
97
® Chemistry : Oxygen Containing Compound
Pre-Medical
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
®
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
98
Chemistry : Oxygen Containing Compound ®
Pre-Medical
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
AE0175
99
® 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
100
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
101