JEE Chemistry Alcohols Phenols and Ethers MCQs Set 15

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Multiple Choice Questions

Question 1: An aromatic amine A was treated with alcoholic potash and another compound Y; a foul-smelling gas \( \ce{C6H5NC} \) was formed. Y was formed by reacting a compound Z with \( \ce{Cl2} \) in the presence of slaked lime. The compound Z is
(a) \( \ce{C6H5NH2} \)
(b) \( \ce{C2H5OH} \)
(c) \( \ce{CH3OCH3} \)
(d) \( \ce{CHCl3} \)
Show Answer & Explanation

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

Explanation:
1. Y is chloroform (carbylamine test), which is made from ethanol and bleaching powder, so Z is ethanol.

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 2: Rectified spirit obtained by fermentation contains 4.5 percent water. To remove it, rectified spirit is mixed with a suitable quantity of benzene. Benzene helps because
(a) It is dehydrating agent and so removes water
(b) It forms the lower layer which retains all the water so that alcohol can be distilled off
(c) It forms an azeotropic mixture having high boiling point and thus allows the alcohol to distil over
(d) It forms low boiling azeotropic mixtures which distil over, leaving behind pure alcohol which can then be distilled
Show Answer & Explanation

Answer: (d) It forms low boiling azeotropic mixtures which distil over, leaving behind pure alcohol which can then be distilled

Explanation:
1. The ternary azeotrope of benzene, ethanol and water boils lower than ethanol, so it distils first carrying away the water.

Teacher's Note:
1. Fermentation uses enzymes: diastase (starch to maltose), maltase (to glucose) and zymase (to ethanol and CO2).
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 3: \( \ce{C6H5OH + ClCOCH3 ->[aq. NaOH] C6H5OCOCH3} \) is an example of
(a) Dow's reaction
(b) Reimer-Tiemann reaction
(c) Schotten-Baumann reaction
(d) Kolbe's reaction
Show Answer & Explanation

Answer: (c) Schotten-Baumann reaction

Explanation:
1. Acylation of a phenol or amine with an acid chloride in aqueous alkali is the Schotten-Baumann reaction.

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 4: Ortho-nitrophenol is steam volatile whereas para-nitrophenol is not. This is due to
(a) Intramolecular hydrogen bonding present in ortho-nitrophenol
(b) Intermolecular hydrogen bonding
(c) Intramolecular hydrogen bonding present in para-nitrophenol
(d) None of these
Show Answer & Explanation

Answer: (a) Intramolecular hydrogen bonding present in ortho-nitrophenol

Explanation:
1. Chelation inside the o-isomer reduces association with water and other molecules, so it is volatile; p-nitrophenol is associated by intermolecular hydrogen bonds.

Teacher's Note:
1. Hydrogen bonding raises boiling point and solubility, while intramolecular bonding (o-nitrophenol) lowers boiling point.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 5: Phenol is less acidic than
(a) Acetic acid
(b) p-Nitrophenol
(c) Both (a) and (b)
(d) None of these
Show Answer & Explanation

Answer: (c) Both (a) and (b)

Explanation:
1. Acetic acid (pKa 4.76) and p-nitrophenol (pKa 7.15) are both stronger acids than phenol (pKa 10).

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. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 6: The strongest acid among the following aromatic compounds is
(a) ortho-Nitrophenol
(b) para-Chlorophenol
(c) para-Nitrophenol
(d) meta-Nitrophenol
Show Answer & Explanation

Answer: (c) para-Nitrophenol

Explanation:
1. The p-nitro group stabilises the phenoxide by both -M and -I effects; pKa about 7.15 against about 8.4 for the meta isomer.

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. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.

Question 7: Diazo-coupling is useful to prepare some
(a) Pesticides
(b) Proteins
(c) Dyes
(d) Vitamins
Show Answer & Explanation

Answer: (c) Dyes

Explanation:
1. Coupling of diazonium salts with phenols or amines gives azo dyes.

Teacher's Note:
1. Diazonium salts give phenol on warming with water and azo dyes by coupling with phenols and amines.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 8: Glycerol reacts with \( \ce{P4 + I2} \) to form
(a) Aldehyde
(b) Allyl iodide
(c) Allyl alcohol
(d) Acetylene
Show Answer & Explanation

Answer: (b) Allyl iodide

Explanation:
1. Phosphorus triiodide (from P + I2) converts glycerol to 2,3-diiodopropanol and then to allyl iodide.

Teacher's Note:
1. Glycerol is propane-1,2,3-triol; it gives nitroglycerine, allyl iodide with HI, and acrolein on dehydration.
2. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 9: The final product formed on reduction of glycerol by hydriodic acid is
(a) Propane
(b) Propanoic acid
(c) Propene
(d) Propyne
Show Answer & Explanation

Answer: (c) Propene

Explanation:
1. Glycerol reacts with HI to give allyl iodide and then isopropyl iodide, which eliminates to propene on heating.

Teacher's Note:
1. Glycerol is propane-1,2,3-triol; it gives nitroglycerine, allyl iodide with HI, and acrolein on dehydration.
2. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.

Question 10: Glycerol was distilled with oxalic acid crystals and the products were led into Fehling solution and warmed. Cuprous oxide was precipitated. It is due to
(a) CO
(b) HCHO
(c) \( \ce{CH3CHO} \)
(d) HCOOH
Show Answer & Explanation

Answer: (d) HCOOH

Explanation:
1. Glycerol with oxalic acid (at 110°C) gives formic acid, a reducing 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.

Question 11: Kolbe-Schmidt reaction is used for
(a) Salicylic acid
(b) Salicylaldehyde
(c) Phenol
(d) Hydrocarbon
Show Answer & Explanation

Answer: (a) Salicylic acid

Explanation:
1. Sodium phenoxide with \( \ce{CO2} \) under pressure gives o-hydroxybenzoic acid.

Teacher's Note:
1. Kolbe-Schmidt reaction: sodium phenoxide with CO2 under pressure gives salicylic acid after acidification.
2. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 12: Which of the following explains the viscous nature of glycerol?
(a) Covalent bonds
(b) Hydrogen bonds
(c) Van der Waals forces
(d) Ionic forces
Show Answer & Explanation

Answer: (b) Hydrogen bonds

Explanation:
1. Three OH groups give extensive intermolecular hydrogen bonding.

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 13: Isopropyl alcohol on oxidation forms
(a) Acetone
(b) Ether
(c) Ethylene
(d) Acetaldehyde
Show Answer & Explanation

Answer: (a) Acetone

Explanation:
1. A secondary alcohol is oxidised to a ketone.

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 14: Benzenediazonium chloride on reaction with phenol in weakly basic medium gives
(a) Diphenyl ether
(b) p-Hydroxyazobenzene
(c) Chlorobenzene
(d) Benzene
Show Answer & Explanation

Answer: (b) p-Hydroxyazobenzene

Explanation:
1. Azo coupling at the para position of phenoxide.

Teacher's Note:
1. Diazonium salts give phenol on warming with water and azo dyes by coupling with phenols and amines.
2. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 15: The alcohol that produces turbidity immediately with \( \ce{ZnCl2} \) + conc. HCl at room temperature is
(a) 1-Hydroxybutane
(b) 2-Hydroxybutane
(c) 2-Hydroxy-2-methylpropane
(d) 1-Hydroxypropane
Show Answer & Explanation

Answer: (c) 2-Hydroxy-2-methylpropane

Explanation:
1. Lucas test: tertiary alcohols give alkyl chloride (turbidity) at once, secondary after about 5 minutes, primary 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 16: The reagent which easily reacts with ethanol and propanol is
(a) Fehling solution
(b) Grignard reagent
(c) Schiff's reagent
(d) Tollens' reagent
Show Answer & Explanation

Answer: (b) Grignard reagent

Explanation:
1. Both are alcohols with acidic OH, which decompose Grignard reagent to give an alkane.

Teacher's Note:
1. Grignard reagents add to carbonyl groups and are destroyed by water, alcohols and acids.
2. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.

Question 17: Which of the following statements is correct?
(a) Phenol is less acidic than ethyl alcohol
(b) Phenol is more acidic than ethyl alcohol
(c) Phenol is more acidic than carboxylic acid
(d) Phenol is more acidic than carbonic acid
Show Answer & Explanation

Answer: (b) Phenol is more acidic than ethyl alcohol

Explanation:
1. Phenoxide is resonance stabilised, so phenol (pKa 10) is more acidic than ethanol (pKa 16) but weaker than carboxylic acids and carbonic acid.

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. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 18: The boiling point of an alcohol is comparatively higher than that of the corresponding alkane due to
(a) Intermolecular hydrogen bonding
(b) Intramolecular hydrogen bonding
(c) Volatile nature
(d) None of these
Show Answer & Explanation

Answer: (a) Intermolecular hydrogen bonding

Explanation:
1. Alcohol molecules are associated through hydrogen bonds.

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 19: When phenol is heated with phthalic anhydride in concentrated sulphuric acid and the hot reaction mixture is poured into a dilute solution of sodium hydroxide, the product is
(a) Alizarin
(b) Fluorescein
(c) Methyl orange
(d) Phenolphthalein
Show Answer & Explanation

Answer: (d) Phenolphthalein

Explanation:
1. Phthalein fusion test: pink colour of phenolphthalein in alkali.

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 20: \( \ce{CH3-CH=CH-CH(OH)-CH3} \) treated with Jones' reagent gives X. Product X is
(a) \( \ce{CH3CH2CH2CH(OH)CH3} \)
(b) \( \ce{CH3CH=CHCOCH3} \)
(c) Both (a) and (b) are correct
(d) \( \ce{CH3CH2CH2COCH3} \)
Show Answer & Explanation

Answer: (b) \( \ce{CH3CH=CHCOCH3} \)

Explanation:
1. Jones reagent oxidises the secondary alcohol to a ketone without affecting the C=C bond.

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 21: Ethylene glycol on oxidation with periodic acid gives
(a) Oxalic acid
(b) Glycol
(c) Formaldehyde
(d) Glycollic acid
Show Answer & Explanation

Answer: (c) Formaldehyde

Explanation:
1. HIO4 cleaves the C-C bond of a 1,2-diol: \( \ce{HOCH2CH2OH -> 2HCHO} \).

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 22: An unknown compound D is first oxidised to an aldehyde and then to acetic acid by a dilute solution of \( \ce{K2Cr2O7} \) and \( \ce{H2SO4} \). The unknown compound D is
(a) \( \ce{CH3CHO} \)
(b) \( \ce{CH3CH2CH2OH} \)
(c) \( \ce{CH3CH2OH} \)
(d) \( \ce{CH3CH2CH3} \)
Show Answer & Explanation

Answer: (c) \( \ce{CH3CH2OH} \)

Explanation:
1. Ethanol gives ethanal then 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 23: The reaction of ethylene glycol with \( \ce{PI3} \) gives
(a) \( \ce{ICH2CH2I} \)
(b) \( \ce{CH2=CH2} \)
(c) \( \ce{CH2=CHI} \)
(d) \( \ce{ICH=CHI} \)
Show Answer & Explanation

Answer: (b) \( \ce{CH2=CH2} \)

Explanation:
1. The unstable 1,2-di-iodoethane loses \( \ce{I2} \) to give ethene.

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 24: The compound A when treated with ceric ammonium nitrate solution gives a yellow precipitate. The compound A is
(a) Alcohol
(b) Aldehyde
(c) Acid
(d) Alkane
Show Answer & Explanation

Answer: (a) Alcohol

Explanation:
1. Alcohols give a coloured (red/yellow) complex with ceric ammonium nitrate; it is a test for the alcoholic OH group.

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 25: During dehydration of alcohols to alkenes by heating with conc. \( \ce{H2SO4} \), the initiation step is
(a) Protonation of alcohol molecule
(b) Formation of carbocation
(c) Elimination of water
(d) Formation of an ester
Show Answer & Explanation

Answer: (a) Protonation of alcohol molecule

Explanation:
1. The alcohol oxygen is first protonated to give \( \ce{ROH2+} \), which then loses water.

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 26: Phenol is less acidic than
(a) Ethanol
(b) Methanol
(c) o-Nitrophenol
(d) p-Methylphenol
Show Answer & Explanation

Answer: (c) o-Nitrophenol

Explanation:
1. The nitro group stabilises the phenoxide, so o-nitrophenol is more acidic than phenol; ethanol and methanol are weaker, and the methyl group lowers acidity.

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 27: The compound which gives the most stable carbocation on dehydration is
(a) \( \ce{(CH3)2CH-CH2OH} \)
(b) \( \ce{(CH3)3C-OH} \)
(c) \( \ce{CH3CH2CH2CH2OH} \)
(d) \( \ce{CH3CH(OH)CH2CH3} \)
Show Answer & Explanation

Answer: (b) \( \ce{(CH3)3C-OH} \)

Explanation:
1. tert-Butyl alcohol gives the tertiary carbocation, the most stable.

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. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 28: Cresol has
(a) Alcoholic -OH
(b) Phenolic -OH
(c) -COOH
(d) -CHO
Show Answer & Explanation

Answer: (b) Phenolic -OH

Explanation:
1. Cresols are methylphenols.

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.

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