JEE Chemistry Alcohols Phenols and Ethers MCQs Set 17

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Chapter-wise Objective Questions: Alcohols Phenols and Ethers

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Multiple Choice Questions

Question 1: The role of conc. \( \ce{H2SO4} \) in the esterification process is
(a) Catalyst
(b) Dehydrating agent
(c) Hydrolysing agent
(d) Dehydrating agent and catalyst
Show Answer & Explanation

Answer: (d) Dehydrating agent and catalyst

Explanation:
1. It protonates the acid (catalyst) and removes water, shifting the equilibrium.

Teacher's Note:
1. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 2: Methanol and ethanol are distinguished by the
(a) Action of HCl
(b) Iodoform test
(c) Solubility in water
(d) Sodium
Show Answer & Explanation

Answer: (b) Iodoform test

Explanation:
1. Only ethanol gives iodoform with \( \ce{I2/NaOH} \).

Teacher's Note:
1. The iodoform test is positive for ethanol, CH3CH(OH)R and CH3CO-; methanol and primary alcohols other than ethanol do not respond.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 3: For phenol, which of the following statements is correct?
(a) It is insoluble in water
(b) It has a lower melting point compared to aromatic hydrocarbons of comparable molecular weight
(c) It has a higher boiling point than toluene
(d) It does not show acidic property
Show Answer & Explanation

Answer: (c) It has a higher boiling point than toluene

Explanation:
1. Hydrogen bonding gives phenol (455 K) a higher boiling point than toluene (384 K).

Teacher's Note:
1. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 4: The reaction of Lucas reagent is fast with
(a) \( \ce{(CH3)3COH} \)
(b) \( \ce{(CH3)2CHOH} \)
(c) \( \ce{CH3(CH2)2OH} \)
(d) \( \ce{CH3CH2OH} \)
Show Answer & Explanation

Answer: (a) \( \ce{(CH3)3COH} \)

Explanation:
1. Tertiary alcohols give turbid alkyl chloride immediately.

Teacher's Note:
1. In the Lucas test turbidity appears at once for tertiary, in about 5 minutes for secondary, and only on heating for primary alcohols.
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 5: Compound A reacts with \( \ce{PCl5} \) to give B which on treatment with KCN followed by hydrolysis gives propanoic acid as the product. What is A?
(a) Ethane
(b) Propane
(c) Ethyl chloride
(d) Ethyl alcohol
Show Answer & Explanation

Answer: (d) Ethyl alcohol

Explanation:
1. The alcohol is converted to ethyl chloride, then to propanenitrile and propanoic acid; A is ethanol.

Teacher's Note:
1. PCl5, PBr3 and SOCl2 replace the OH of alcohols by halogen; HX with ZnCl2 does the same via carbocations.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 6: Which reagent can convert acetic acid into ethanol?
(a) Na + alcohol
(b) \( \ce{LiAlH4} \) + ether
(c) \( \ce{H2} \) + Pt
(d) Sn + HCl
Show Answer & Explanation

Answer: (b) \( \ce{LiAlH4} \) + ether

Explanation:
1. LiAlH4 reduces carboxylic acids to primary alcohols.

Teacher's Note:
1. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 7: Phenol and benzoic acid can be distinguished by
(a) NaOH
(b) \( \ce{NaHCO3} \)
(c) \( \ce{Na2CO3} \)
(d) \( \ce{H2SO4} \)
Show Answer & Explanation

Answer: (b) \( \ce{NaHCO3} \)

Explanation:
1. Benzoic acid liberates \( \ce{CO2} \) from \( \ce{NaHCO3} \); phenol is too weak an acid to do so.

Teacher's Note:
1. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.
2. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.

Question 8: Electrophilic substitution reaction in phenol takes place at
(a) p-position
(b) m-position
(c) o-position
(d) o- and p-positions
Show Answer & Explanation

Answer: (d) o- and p-positions

Explanation:
1. The OH group activates and directs to the ortho and para positions.

Teacher's Note:
1. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 9: The boiling point of glycerol is higher than that of propanol because of
(a) Hydrogen bonding
(b) Hybridisation
(c) Resonance
(d) All of the above
Show Answer & Explanation

Answer: (a) Hydrogen bonding

Explanation:
1. Glycerol has three OH groups and more extensive hydrogen bonding.

Teacher's Note:
1. Hydrogen bonding raises boiling point and solubility, while intramolecular bonding (o-nitrophenol) lowers boiling point.
2. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 10: Which of the following produces violet colour with \( \ce{FeCl3} \) solution?
(a) Enols
(b) Ethanol
(c) Ethanal
(d) Alkyl halides
Show Answer & Explanation

Answer: (a) Enols

Explanation:
1. Phenols and enols give a coloured complex with neutral ferric chloride.

Teacher's Note:
1. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.
2. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.

Question 11: When heated with \( \ce{NH3} \) under pressure alone or in the presence of zinc chloride, phenols are converted into
(a) Aminophenols
(b) Aniline
(c) Nitrobenzene
(d) Phenyl hydroxylamine
Show Answer & Explanation

Answer: (b) Aniline

Explanation:
1. The OH is replaced by NH2.

Teacher's Note:
1. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 12: Because of resonance the oxygen atom of the -OH group of phenol
(a) Acquires positive charge
(b) Acquires negative charge
(c) Remains unaffected
(d) Liberates
Show Answer & Explanation

Answer: (a) Acquires positive charge

Explanation:
1. The lone pair on oxygen delocalises into the ring, leaving oxygen partly positive.

Teacher's Note:
1. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.
2. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 13: An organic compound X on treatment with acidified \( \ce{K2Cr2O7} \) gives a compound Y which reacts with \( \ce{I2} \) and sodium carbonate to form tri-iodomethane. The compound X is
(a) \( \ce{CH3OH} \)
(b) \( \ce{CH3-CO-CH3} \)
(c) \( \ce{CH3CHO} \)
(d) \( \ce{CH3CH(OH)CH3} \)
Show Answer & Explanation

Answer: (d) \( \ce{CH3CH(OH)CH3} \)

Explanation:
1. Y must have the \( \ce{CH3CO-} \) group; the alcohol that gives it on oxidation is propan-2-ol (acetone).

Teacher's Note:
1. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.
2. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.

Question 14: The reaction of conc. \( \ce{HNO3} \) and phenol forms
(a) Benzoic acid
(b) Salicylic acid
(c) o- and p-nitrophenol
(d) Picric acid
Show Answer & Explanation

Answer: (d) Picric acid

Explanation:
1. Conc. nitric acid (with sulphuric acid) nitrates all three activated positions to give picric acid.

Teacher's Note:
1. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 15: Phenol is
(a) A weaker base than \( \ce{NH3} \)
(b) Stronger than carbonic acid
(c) Weaker than carbonic acid
(d) A neutral compound
Show Answer & Explanation

Answer: (c) Weaker than carbonic acid

Explanation:
1. Phenol (pKa about 10) is weaker than carbonic acid (pKa1 about 6.4).

Teacher's Note:
1. Acidity order: carboxylic acids > carbonic acid > phenol > water > alcohols; nitro groups increase and alkyl groups decrease the acidity of phenols.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 16: Phenol at 25°C is
(a) A white crystalline solid
(b) A transparent liquid
(c) A gas
(d) A yellow solution
Show Answer & Explanation

Answer: (a) A white crystalline solid

Explanation:
1. Pure phenol is a colourless to white crystalline solid (m.p. 314 K), turning pink on oxidation.

Teacher's Note:
1. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 17: Oxidation of ethanol by chromic acid forms
(a) Ethanol (no change)
(b) Methanol
(c) 2-Propanone
(d) Ethanoic acid
Show Answer & Explanation

Answer: (d) Ethanoic acid

Explanation:
1. Excess chromic acid oxidises ethanol through ethanal to ethanoic acid.

Teacher's Note:
1. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 18: Which of the following does not give effervescence with \( \ce{NaHCO3} \)?
(a) Phenol
(b) Benzoic acid
(c) 2,4-Dinitrophenol
(d) 2,4,6-Trinitrophenol
Show Answer & Explanation

Answer: (a) Phenol

Explanation:
1. Phenol (pKa 10) is weaker than carbonic acid and cannot decompose bicarbonate. 2,4-Dinitrophenol (pKa 4.1) and picric acid (pKa 0.4) are stronger than carbonic acid.
2. Benzoic acid also gives effervescence.

Teacher's Note:
1. Acidity order: carboxylic acids > carbonic acid > phenol > water > alcohols; nitro groups increase and alkyl groups decrease the acidity of phenols.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 19: Conc. \( \ce{H2SO4} \) reacts with \( \ce{C2H5OH} \) at 170°C to form
(a) \( \ce{CH3COCH3} \)
(b) \( \ce{CH3COOH} \)
(c) \( \ce{CH3CHO} \)
(d) \( \ce{C2H4} \)
Show Answer & Explanation

Answer: (d) \( \ce{C2H4} \)

Explanation:
1. Dehydration gives ethene.

Teacher's Note:
1. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 20: Which compound has hydrogen bonding?
(a) Toluene
(b) Phenol
(c) Chlorobenzene
(d) Nitrobenzene
Show Answer & Explanation

Answer: (b) Phenol

Explanation:
1. Only phenol has an O-H group.

Teacher's Note:
1. Hydrogen bonding raises boiling point and solubility, while intramolecular bonding (o-nitrophenol) lowers boiling point.
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 21: Read the statements. (A) A secondary alcohol on oxidation gives a ketone. (B) Ethanol reacts with conc. \( \ce{H2SO4} \) at 180°C to yield ethylene. (C) Methanol reacts with iodine and sodium hydroxide to give a yellow precipitate of iodoform. (D) Hydrogen gas is liberated when sodium is added to alcohol. Select the correct set.
(a) A, B
(b) C, D
(c) A, B, D
(d) A, C, D
Show Answer & Explanation

Answer: (c) A, B, D

Explanation:
1. Methanol has no \( \ce{CH3CH(OH)-} \) or \( \ce{CH3CO-} \) group, so (C) is false; the others are true.

Teacher's Note:
1. The iodoform test is positive for ethanol, CH3CH(OH)R and CH3CO-; methanol and primary alcohols other than ethanol do not respond.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 22: The reaction of phenol with \( \ce{HCl + HCN} \) in the presence of anhydrous \( \ce{ZnCl2} \) to give o-hydroxybenzaldehyde is known as
(a) Perkin reaction
(b) Gattermann reaction
(c) Kolbe reaction
(d) Gattermann-Koch reaction
Show Answer & Explanation

Answer: (b) Gattermann reaction

Explanation:
1. Formylation of phenols and ethers using HCN/HCl with \( \ce{ZnCl2} \) is the Gattermann reaction; the Gattermann-Koch reaction uses CO/HCl with benzene.

Teacher's Note:
1. Ethers are cleaved by HI, form explosive peroxides in air, and act as Lewis bases forming etherates.
2. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 23: The carbylamine test is done by heating alcoholic KOH with
(a) Chloroform and silver powder
(b) Trihalogen methane and primary amine
(c) Alkyl halide and primary amine
(d) Alkyl cyanide and primary amine
Show Answer & Explanation

Answer: (b) Trihalogen methane and primary amine

Explanation:
1. A trihalomethane (chloroform) with a primary amine and alcoholic KOH gives an isocyanide.

Teacher's Note:
1. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.
2. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.

Question 24: Isopropyl alcohol heated at 300°C with a copper catalyst forms
(a) Acetone
(b) Dimethyl ether
(c) Acetaldehyde
(d) Ethane
Show Answer & Explanation

Answer: (a) Acetone

Explanation:
1. Dehydrogenation of a secondary alcohol gives a ketone.

Teacher's Note:
1. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 25: In the sequence \( \ce{CH3OH ->[HI] CH3I ->[KCN] CH3CN ->[reduction] X ->[HNO2] Y} \), X and Y are respectively
(a) \( \ce{CH3CH2NH2} \) and \( \ce{CH3CH2OH} \)
(b) \( \ce{CH3CH2NH2} \) and \( \ce{CH3COOH} \)
(c) \( \ce{CH3CH2OH} \) and \( \ce{CH3CHO} \)
(d) \( \ce{CH3OCH3} \) and \( \ce{CH3CHO} \)
Show Answer & Explanation

Answer: (a) \( \ce{CH3CH2NH2} \) and \( \ce{CH3CH2OH} \)

Explanation:
1. Reduction of the nitrile gives ethylamine, and nitrous acid converts the primary amine to ethanol.

Teacher's Note:
1. Nitro groups at ortho and para positions increase the acidity of phenol, and ortho-nitrophenol is steam volatile.
2. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 26: The alcohols (i) \( \ce{CH3CH2CH2OH} \), (ii) \( \ce{CH3CH(OH)CH3} \) and (iii) \( \ce{(CH3)3C-OH} \) were treated with Lucas reagent (conc. HCl + \( \ce{ZnCl2} \)). What results do you expect at room temperature?
(a) (ii) and (iii) react immediately and (i) in about 5 minutes
(b) (iii) reacts immediately, (ii) in about 5 minutes and (i) not at all
(c) (i) reacts immediately, (ii) in about 5 minutes and (iii) not at all
(d) (i) in about 5 minutes, (ii) in about 15 minutes and (iii) not at all
Show Answer & Explanation

Answer: (b) (iii) reacts immediately, (ii) in about 5 minutes and (i) not at all

Explanation:
1. Lucas reaction goes through carbocations: tertiary at once, secondary in about 5 minutes, primary only on heating.

Teacher's Note:
1. In the Lucas test turbidity appears at once for tertiary, in about 5 minutes for secondary, and only on heating for primary alcohols.
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 27: Ethylene may be obtained by dehydration of which of the following with conc. \( \ce{H2SO4} \) at 160-170°C?
(a) \( \ce{C2H5OH} \)
(b) \( \ce{CH3OH} \)
(c) \( \ce{CH3CH2CH2OH} \)
(d) \( \ce{(CH3)2CHCH2OH} \)
Show Answer & Explanation

Answer: (a) \( \ce{C2H5OH} \)

Explanation:
1. Only ethanol has two carbons and gives ethene.

Teacher's Note:
1. Dehydration of alcohols follows carbocation stability, so tertiary alcohols dehydrate fastest; ethanol gives ether at 413 K and ethene at 443 K.
2. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.

Question 28: The final product of the oxidation of ethyl alcohol is
(a) Ethane
(b) Acetone
(c) Acetaldehyde
(d) Acetic acid
Show Answer & Explanation

Answer: (d) Acetic acid

Explanation:
1. Ethanol is oxidised to ethanal and then to ethanoic acid.

Teacher's Note:
1. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.
2. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

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Multiple Choice Questions (MCQs) for JEE Chemistry Alcohols Phenols and Ethers

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