Q1: 1-methyl ethylene oxide when treated with an excess of HBr produces:

(A)

(B)

(C)

(D)
Q1: 1-methyl ethylene oxide when treated with an excess of HBr produces:
(A)

(B)

(C)

(D)
Solution:
Q2: A chromatography column, packed with silica gel as stationary phase, was used to
separate a mixture of compounds consisting of (A) benzanilide, (B) aniline and (C)
acetophenone. When the column is eluted with a mixture of solvents, hexane : ethyl acetate
(20:80), the sequence of obtained compounds is:
(A) (B), (A) and (C)

(B) (C), (A) and (B)

(C) (B), (C) and (A)

(D) (A), (B) and (C)

Q2: A chromatography column, packed with silica gel as stationary phase, was used to
separate a mixture of compounds consisting of (A) benzanilide, (B) aniline and (C)
acetophenone. When the column is eluted with a mixture of solvents, hexane : ethyl acetate
(20:80), the sequence of obtained compounds is:
(A) (B), (A) and (C)

(B) (C), (A) and (B)

(C) (B), (C) and (A)

(D) (A), (B) and (C)

Solution:

Since the column is eluted with the solvent having more proportion of ethyl acetate, the more polar compound will come out
first.

The order of polarity in the given compounds is; acetophenone > benzanilide > aniline.

(Dipolemoment (μ) of acetophenone=3.05 D, benzanilide=2.71 D and aniline=1.59 D).

Q3: In the following reaction sequence, structures of A and B, respectively will be:

(A)

(B)

(C)

(D)
Q3: In the following reaction sequence, structures of A and B, respectively will be:

(A)

(B)

(C)

(D)
Solution:
Q4: The major product in the following reaction is:

(A)

(B)

(C)

(D)
Q4: The major product in the following reaction is:

(A)

(B)

(C)

(D)
Solution:
Q5: Among the following compounds A and B with molecular formula C9H18O3, A is having
higher boiling point than B. The possible structures of A and B are:
(A)

(B)

(C)

(D)
Q5: Among the following compounds A and B with molecular formula C9H18O3, A is having
higher boiling point than B. The possible structures of A and B are:
(A)

(B)

(C)

(D)

Solution:

In option b compound A has extensive inter-molecular hydrogen bonding because of the 3 −OH groups while in compound B
there are −OCH3 groups present and no inter-molecular hydrogen bonding is possible.
Q6: The major aromatic product C in the following reaction sequence will be :

(A)

(B)

(C)

(D)
Q6: The major aromatic product C in the following reaction sequence will be :

(A)

(B)

(C)

(D)
Solution:

Hence, Option (c) is correct

Q7: Consider the following reaction :

The product ‘P’ gives a positive ceric ammonium nitrate test. This is because of the presence
of which of these – OH group (s) ?
(A) (b) only

(B) (b) and (d)

(C) (c) and (d)

(D) (d) only

Q7: Consider the following reaction :

The product ‘P’ gives a positive ceric ammonium nitrate test. This is because of the presence
of which of these – OH group (s) ?
(A) (b) only

(B) (b) and (d)

(C) (c) and (d)

(D) (d) only

Solution:
Q8: When neopentyl alcohol is heated with an acid, it slowly converted into an 85 : 15 mixture
of alkenes A and B, respectively. What are these alkenes?
(A)

(B)

(C)

(D)
Q8: When neopentyl alcohol is heated with an acid, it slowly converted into an 85 : 15 mixture
of alkenes A and B, respectively. What are these alkenes?
(A)

(B)

(C)

(D)
Solution:

Hence, option (c) is correct

Q9: An organic compound (A) (molecular formula C6H12O2) was hydrolysed with dil. H2SO4 to
give a carboxylic acid (B) and an alcohol (C). ‘C’ gives white turbidity immediately when
treated with anhydrous ZnCl2 and conc. HCl. The organic compound (A) is:
(A)

(B)

(C)

(D)
Q9: An organic compound (A) (molecular formula C6H12O2) was hydrolysed with dil. H2SO4 to
give a carboxylic acid (B) and an alcohol (C). ‘C’ gives white turbidity immediately when
treated with anhydrous ZnCl2 and conc. HCl. The organic compound (A) is:
(A)

(B)

(C)

(D)
Solution:
Q10: The major product [B] in the following reactions is-

(A)

(B)

(C)

(D)
Q10: The major product [B] in the following reactions is-

(A)

(B)

(C)

(D)

Solution:

Q11: The increasing order of boiling points of the following is :

(A) I < III < IV < II

(B) III < I < II < IV

(C) I < IV < III < II

(D) III < IV < II < I

Q11: The increasing order of boiling points of the following is :

(A) I < III < IV < II

(B) III < I < II < IV

(C) I < IV < III < II

(D) III < IV < II < I

Solution:

Increasing order of boiling point is 

⇒ Shows hydrogen bonding from O-H group only

⇒ Shows strongest hydrogen bonding from both sides of -OH group as well as -NO2 group

⇒ Shows strongest hydrogen bonding from both sides of -OH group as well as -NH2 group
⇒ Shows stronger hydrogen from one side of -OH group and another side of -OCH3 group shows only dipole-dipole
interaction

⇒ Hence correct order of boiling point is 

     (I) < (IV) < (III) < (II)

Q12: What is the final product (major) ‘A’ in the given reaction?

(A)

(B)

(C)

(D)
Q12: What is the final product (major) ‘A’ in the given reaction?

(A)

(B)

(C)

(D)
Solution:
Q13: Which of the following compound gives pink colour on reaction with phthalic anhydride
in conc. H2SO4 followed by treatment with NaOH?
(A)

(B)

(C)

(D)
Q13: Which of the following compound gives pink colour on reaction with phthalic anhydride
in conc. H2SO4 followed by treatment with NaOH?
(A)

(B)

(C)

(D)
Solution:
Q14: What is ‘X’ in the given reaction?

(A)

(B)

(C)

(D)
Q14: What is ‘X’ in the given reaction?

(A)

(B)

(C)

(D)

Solution:
Q15: Given below are two statements :

Statement I : o-Nitrophenol is steam volatile due to intramolecular hydrogen bonding.

Statement II : o-Nitrophenol has high melting due to hydrogen bonding.

In the light of the above statements, choose the most appropriate answer from the options
given below
(A) Both statement I and statement II are false

(B) statement I is false but statement II is true

(C) Statement I is true but statement II is false

(D) Both statement I and statement II are true

Q15: Given below are two statements :

Statement I : o-Nitrophenol is steam volatile due to intramolecular hydrogen bonding.

Statement II : o-Nitrophenol has high melting due to hydrogen bonding.

In the light of the above statements, choose the most appropriate answer from the options
given below
(A) Both statement I and statement II are false

(B) statement I is false but statement II is true

(C) Statement I is true but statement II is false

(D) Both statement I and statement II are true

Solution:

Ortho nitro phenol is stream volatile due to Intramolecular H-bonding while p-nitro phenol is less volatile due to
interamolecular H-bonding.

p-nitro phenol has high melting point due to more symmetric in nature.
Q16: Identify the major products A and B respectively in the following reactions of phenol :

(A)

(B)

(C)

(D)
Q16: Identify the major products A and B respectively in the following reactions of phenol :

(A)

(B)

(C)

(D)
Solution:
Q17: Ceric ammonium nitrate and CHCl3/alc. KOH are used for the identification of functional
groups present in _______ and _______ respectively.
(A) Alcohol, amine

(B) Amine, phenol

(C) Alcohol, phenol

(D) Amine, alcohol

Q17: Ceric ammonium nitrate and CHCl3/alc. KOH are used for the identification of functional
groups present in _______ and _______ respectively.
(A) Alcohol, amine

(B) Amine, phenol

(C) Alcohol, phenol

(D) Amine, alcohol

Solution:

Alcohols give the positive test with Ceric ammonium nitrate & 1º amines give the positive test with CHCl3 + KOH i.e.
carbylamine test.
Q18: Identify A in the given reaction.

(A)

(B)

(C)
(D)
Q18: Identify A in the given reaction.

(A)

(B)

(C)
(D)

Solution:
Q19: Reaction of Grignard reagent, with followed by hydrolysis gives
compound “A” which reacts instantly with Lucas reagent to give compound B,

The Compound B is:

(A)

(B)

(C)

(D)
Q19: Reaction of Grignard reagent, with followed by hydrolysis gives
compound “A” which reacts instantly with Lucas reagent to give compound B,

The Compound B is:

(A)

(B)

(C)

(D)
Solution:

Q20: Main product formed during a reaction of 1-methoxy naphthalene with hydroiodic acid
are :
(A)

(B)

(C)

(D)
Q20: Main product formed during a reaction of 1-methoxy naphthalene with hydroiodic acid
are :
(A)

(B)

(C)

(D)
Solution:
Q21: Which of the following compounds will provide a tertiary alcohol on reaction with excess
of followed by hydrolysis?
(A)

(B)

(C)

(D)
Q21: Which of the following compounds will provide a tertiary alcohol on reaction with excess
of followed by hydrolysis?
(A)

(B)

(C)

(D)
Solution:

Q22: An organic compound A gives dark green coloration with ferric chloride. On
treatment with and KOH, followed by acidification gives compound B. Compound B
can also be obtained from compound C on reaction with pyridinium chlorochromate (PCC).
Identify A, B and C.
(A)

(B)

(C)

(D)
Q22: An organic compound A gives dark green coloration with ferric chloride. On
treatment with and KOH, followed by acidification gives compound B. Compound B
can also be obtained from compound C on reaction with pyridinium chlorochromate (PCC).
Identify A, B and C.
(A)

(B)

(C)

(D)
Solution:
Q23:  

Consider the above reaction, the major product ‘P’ is:

(A)

(B)

(C)

(D)
Q23:  

Consider the above reaction, the major product ‘P’ is:

(A)

(B)

(C)

(D)
Solution:
Q24:

(Major product)

The given reaction can occur in the presence of:

(i) Bromine water (ii) in

(iii) (iv) in

Choose the correct answer from the options given below:

(A) (ii) and (iv) only

(B) (i) and (iii) only

(C) (ii), (iii) and (iv) only

(D) (i), (ii) and (iv) only

Q24:

(Major product)

The given reaction can occur in the presence of:

(i) Bromine water (ii) in

(iii) (iv) in

Choose the correct answer from the options given below:

(A) (ii) and (iv) only

(B) (i) and (iii) only

(C) (ii), (iii) and (iv) only

(D) (i), (ii) and (iv) only

Solution:

Bromine water gives tribromo derivatives while rest other give mono bromo product in which para product is major product
Q25:

Consider the above reaction, the major product "P" formed is:
(A)

(B)

(C)

(D)
Q25:

Consider the above reaction, the major product "P" formed is:
(A)

(B)

(C)

(D)
Solution:
Q26: The correct options for the products A and B of the following reactions are:

(A)

(B)

(C)

(D)
Q26: The correct options for the products A and B of the following reactions are:

(A)

(B)

(C)

(D)
Solution:
Q27: Which one of the following phenols does not give colour when condensed with phthalic
anhydride in presence of conc. H2SO4?
(A)

(B)

(C)

(D)
Q27: Which one of the following phenols does not give colour when condensed with phthalic
anhydride in presence of conc. H2SO4?
(A)

(B)

(C)

(D)

Solution:

Only p-methylphenol does not give any colour with phthalic anhydroxide with conc. H2SO4.
Q28: Given below are two statements: one is labelled as :Assertion (A) and the other is
labelled as Reason (R).
Assertion (A): Synthesis of ethyl phenyl ether may be achieved by Williamson synthesis.

Reason (R): Reaction of bromobenzene with sodium ethoxide yields ethyl phenyl ether.

In the light of the above statements, choose the most appropriate answer from the options
given

below
(A) Both (A) and (R) are correct and (R) is the correct explanation of (A)

(B) (A) is correct but (R) is not correct

(C) (A) is not correct but (R) is correct

(D) Both (A) and (R) are correct but (R) is NOT the correct explanation of (A)
Q28: Given below are two statements: one is labelled as :Assertion (A) and the other is
labelled as Reason (R).
Assertion (A): Synthesis of ethyl phenyl ether may be achieved by Williamson synthesis.

Reason (R): Reaction of bromobenzene with sodium ethoxide yields ethyl phenyl ether.

In the light of the above statements, choose the most appropriate answer from the options
given

below
(A) Both (A) and (R) are correct and (R) is the correct explanation of (A)

(B) (A) is correct but (R) is not correct

(C) (A) is not correct but (R) is correct

(D) Both (A) and (R) are correct but (R) is NOT the correct explanation of (A)
Solution:

Q29: The major product of the following reaction, if it occurs by SN2 mechanism is

(A)

(B)

(C)

(D)
Q29: The major product of the following reaction, if it occurs by SN2 mechanism is

(A)

(B)

(C)

(D)
Solution:
Q30: The intermediate X, in the reaction:

(A)

 
(B)

(C)

 
(D)

 
Q30: The intermediate X, in the reaction:

(A)

 
(B)

(C)

 
(D)

Solution:
Q31: In the following reaction:

The compounds A and B respectively are:

(A)

(B)
(C)

(D)
Q31: In the following reaction:

The compounds A and B respectively are:

(A)

(B)
(C)

(D)

Solution:

Cumene hydroperoxide undergoes rearrangement to give phenol & acetone.

Q32: Match List I with List II.

List I List II

A. I. Br2 in CS2

B. II. Na2Cr2O7/H2SO4

C. III. Zn

D. IV. CHCl3/NaOH

Choose the correct answer from the options. given below

(A) A → IV; B → III; C → II; D → I

(B) A → IV; B → III; C → I; D → II

(C) A → II; B → III; C → I; D → IV

(D) A → IV; B → II; C → III; D → I

Q32: Match List I with List II.

List I List II

A. I. Br2 in CS2

B. II. Na2Cr2O7/H2SO4

C. III. Zn

D. IV. CHCl3/NaOH

Choose the correct answer from the options. given below

(A) A → IV; B → III; C → II; D → I

(B) A → IV; B → III; C → I; D → II

(C) A → II; B → III; C → I; D → IV

(D) A → IV; B → II; C → III; D → I

Solution:

Q33: The major product (P) of the given reaction is

(where, Me is –CH3)

(A)

(B)

(C)

(D)
Q33: The major product (P) of the given reaction is

(where, Me is –CH3)

(A)

(B)

(C)

(D)
Solution:

Q34: Given below are two statements

Statement I: Phenols are weakly acidic.

Statement II: Therefore they are freely soluble in NaOH solution and are weaker acids than
alcohols and water.

Choose the most appropriate option:

(A) Both Statement I and Statement II are correct

(B) Both Statement I and Statement II are incorrect

(C) Statement I is correct but Statement II is incorrect

(D) Statement I is incorrect but Statement II is correct

Q34: Given below are two statements

Statement I: Phenols are weakly acidic.

Statement II: Therefore they are freely soluble in NaOH solution and are weaker acids than
alcohols and water.

Choose the most appropriate option:

(A) Both Statement I and Statement II are correct

(B) Both Statement I and Statement II are incorrect

(C) Statement I is correct but Statement II is incorrect

(D) Statement I is incorrect but Statement II is correct

Solution:

Phenols are weakly acidic; However, Phenol is more acidic than alcohol and water .Phenol is more acidic than alcohols due to
stabilization of phenoxide ion through resonance.

No such resonance is present in water after loosing a proton, which makes water less acidic than phenols.

So, statement I is correct , but statement II is incorrect.

Q35: Most stable product of the following reaction is:

(A)

(B)

(C)

(D)

Q35: Most stable product of the following reaction is:

(A)

(B)

(C)

(D)

Solution:

Q36: Given below are two statements:

Statement I: On heating with KHSO4, glycerol is dehydrated and acrolein is formed.

Statement II: Acrolein has fruity odour and can be used to test glycerol's presence.

Choose the correct option.

(A) Both Statement I and Statement II are correct.

(B) Both Statement I and Statement II are incorrect

(C) Statement I is correct but Statement II is incorrect.

(D) Statement I is incorrect but Statement II is correct.

Q36: Given below are two statements:

Statement I: On heating with KHSO4, glycerol is dehydrated and acrolein is formed.

Statement II: Acrolein has fruity odour and can be used to test glycerol's presence.

Choose the correct option.

(A) Both Statement I and Statement II are correct.

(B) Both Statement I and Statement II are incorrect

(C) Statement I is correct but Statement II is incorrect.

(D) Statement I is incorrect but Statement II is correct.

Solution:

Acrolein has pungent, suffocating odour and it is used to detect presence of glycerol.
Q37: The difference in the reaction of phenol with bromine in chloroform and bromine in water
medium is due to:
(A) Hyperconjugation in substrate

(B) Polarity of solvent

(C) Free radical formation

(D) Electromeric effect of the substrate

Q37: The difference in the reaction of phenol with bromine in chloroform and bromine in water
medium is due to:
(A) Hyperconjugation in substrate

(B) Polarity of solvent

(C) Free radical formation

(D) Electromeric effect of the substrate

Solution:

Phenol gives different products with bromine in chloroform and water medium due to the polarity difference between
chloroform and water acting as solvent
Q38: Which reactant will give the following alcohol on reaction with one mole of phenyl
magnesium bromide (PhMgBr) followed by acidic hydrolysis?

(A) CH3 – C ≡ N

(B) Ph – C ≡ N

(C)

(D)
Q38: Which reactant will give the following alcohol on reaction with one mole of phenyl
magnesium bromide (PhMgBr) followed by acidic hydrolysis?

(A) CH3 – C ≡ N

(B) Ph – C ≡ N

(C)

(D)

Solution:
Q39: Hydrolysis of which compound will give carbolic acid ?
(A) Cumene

(B) Benzenediazonium chloride

(C) Benzal chloride

(D) Ethylene glycol ketal

Q39: Hydrolysis of which compound will give carbolic acid ?
(A) Cumene

(B) Benzenediazonium chloride

(C) Benzal chloride

(D) Ethylene glycol ketal

Solution:

Phenol is known as Carbolic acid.

Diazonium salts are hydrolysed to phenols.

Q40: Choose the correct option for the following reactions.

(A) ‘A’ and ‘B’ are both Markovnikov addition products.

(B) ‘A’ is Markovnikov product and ‘B’ is anti-Markovnikov product.

(C) ‘A’ and ‘B’ are both anti-Markovnikov products.

(D) ‘B’ is Markovnikov and ‘A’ is anti-Markovnikov product.

Q40: Choose the correct option for the following reactions.

(A) ‘A’ and ‘B’ are both Markovnikov addition products.

(B) ‘A’ is Markovnikov product and ‘B’ is anti-Markovnikov product.

(C) ‘A’ and ‘B’ are both anti-Markovnikov products.

(D) ‘B’ is Markovnikov and ‘A’ is anti-Markovnikov product.

Solution:

Q41: Identify the major product A and B for the below given reaction sequence.

(A)

(B)
(C)

(D)
Q41: Identify the major product A and B for the below given reaction sequence.

(A)

(B)
(C)

(D)
Solution:

Q42: Compound I is heated with Conc. HI to give a hydroxy compound A which is further
heated with Zn dust to give compound B. Identify A and B.

(A)

(B)

(C)

(D)
Q42: Compound I is heated with Conc. HI to give a hydroxy compound A which is further
heated with Zn dust to give compound B. Identify A and B.

(A)

(B)

(C)

(D)
Solution:

Q43: Consider the below reaction sequence, the Product ‘C’ is :

(A)

(B)

(C)

(D)
Q43: Consider the below reaction sequence, the Product ‘C’ is :

(A)

(B)

(C)

(D)
Solution:
Q44: A compound 'X' is acidic and it is soluble in NaOH solution, but insoluble in NaHCO3
solution. Compound 'X' also gives violet colour with neutral FeCI3 solution. The compound 'X'
is:
(A)

(B)

(C)

(D)
Q44: A compound 'X' is acidic and it is soluble in NaOH solution, but insoluble in NaHCO3
solution. Compound 'X' also gives violet colour with neutral FeCI3 solution. The compound 'X'
is:
(A)

(B)

(C)

(D)
Solution:
Q45: When enthanol is heated with conc. H2SO4, a gas is produced. The compound formed,
when this gas is treated with cold dilute aqueous solution of Baeyer's reagent, is :
(A) Formaldehyde

(B) Formic acid

(C) Glycol

(D) Ethanoic acid

Q45: When enthanol is heated with conc. H2SO4, a gas is produced. The compound formed,
when this gas is treated with cold dilute aqueous solution of Baeyer's reagent, is :
(A) Formaldehyde

(B) Formic acid

(C) Glycol

(D) Ethanoic acid

Solution:
Q46: Two compounds A and B with same molecular formula (C3H6O) undergo Grignard’s
reaction with methyl magnesium bromide to give products C and D. Products C and D show
following chemical tests.

Test C D
Ceric ammonium nitrate
Positive Positive
Test
Turbidity obtained after five Turbidity obtained
Lucas Test
minutes immediately
Iodoform Test Positive Negative

C and D respectively are :

(A)

(B)
(C)

(D)
Q46: Two compounds A and B with same molecular formula (C3H6O) undergo Grignard’s
reaction with methyl magnesium bromide to give products C and D. Products C and D show
following chemical tests.

Test C D
Ceric ammonium nitrate
Positive Positive
Test
Turbidity obtained after five Turbidity obtained
Lucas Test
minutes immediately
Iodoform Test Positive Negative

C and D respectively are :

(A)

(B)
(C)

(D)

Solution:
Q47: A solution of phenol in chloroform when treated with aqueous NaOH gives compound P
as a major product. The mass percentage of carbon in P is .......... (to the nearest integer)

(Atomic mass: C = 12; H = 1 ; O = 16)

Q47: A solution of phenol in chloroform when treated with aqueous NaOH gives compound P
as a major product. The mass percentage of carbon in P is .......... (to the nearest integer)

(Atomic mass: C = 12; H = 1 ; O = 16)

69

Solution:

Mass of Salicylaldehyde = 12 × 7 + 6 × 1 + 16 × 2 = 122

Mass of carbon = 12 × 7 = 84

The mass % of carbon .

Q48: To synthesize 1.0 mole of 2-methylpropan-2-ol from ethyl ethanoate ________
equivalents of regent will be required. (Integer value)
Q48: To synthesize 1.0 mole of 2-methylpropan-2-ol from ethyl ethanoate ________
equivalents of regent will be required. (Integer value)
2.00

Solution:
Q49: Compound ‘P’ on nitration with dil. HNO3 yields two isomers (A) and (B). These isomers
can be separated by steam distillation. Isomers (A) and (B) show the intramolecular and
intermolecular hydrogen bonding respectively. Compound (P) on reaction with conc. HNO3
yields a yellow compound ‘C’, a strong acid. The number of oxygen atoms is present in
compound ‘C’_____.
Q49: Compound ‘P’ on nitration with dil. HNO3 yields two isomers (A) and (B). These isomers
can be separated by steam distillation. Isomers (A) and (B) show the intramolecular and
intermolecular hydrogen bonding respectively. Compound (P) on reaction with conc. HNO3
yields a yellow compound ‘C’, a strong acid. The number of oxygen atoms is present in
compound ‘C’_____.
7.00

Solution:

Compound P is phenol.
Compound C is picric acid and No. of O-atoms in C is 7

Q50: In the given reaction,

the number of sp2 hybridised carbon(s) in compound ‘X’ is

Q50: In the given reaction,

the number of sp2 hybridised carbon(s) in compound ‘X’ is

8.00
Solution:

The number of sp2 hybridised carbon atoms is 8.

Q51: The number of non-ionisable protons present in the product B obtained from the
following reaction is _____. C2H5OH + PCl3 C2H5Cl + A

A + PCl3 B
Q51: The number of non-ionisable protons present in the product B obtained from the
following reaction is _____. C2H5OH + PCl3 C2H5Cl + A

A + PCl3 B
2.00

Solution:

Structure of H4P2O5

Total 2 non-ionizable protons are present

Q52:

consider the above reaction, and choose the correct statement:

(A) The reaction is not possible in acidic medium

(B) Both compounds A and B are formed equally

(C) Compound A will be the major product

(D) Compound B will be the major product

Q52:

consider the above reaction, and choose the correct statement:

(A) The reaction is not possible in acidic medium

(B) Both compounds A and B are formed equally

(C) Compound A will be the major product

(D) Compound B will be the major product

Solution:

Due to steric crowding trans alkene is more stable.