JEE Chemistry Alcohols Phenols and Ethers MCQs Set 20

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

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Multiple Choice Questions

Question 1: Diethyl ether can be decomposed by heating with
(a) HI
(b) NaOH
(c) Water
(d) \( \ce{KMnO4} \)
Show Answer & Explanation

Answer: (a) HI

Explanation:
1. Hydroiodic acid cleaves the ether linkage.

Teacher's Note:
1. Ethers are cleaved by HI, form explosive peroxides in air, and act as Lewis bases forming etherates.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 2: On boiling with concentrated hydrobromic acid, phenyl ethyl ether will yield
(a) Phenol and ethyl bromide
(b) Phenol and ethane
(c) Bromobenzene and ethanol
(d) Bromobenzene and ethane
Show Answer & Explanation

Answer: (a) Phenol and ethyl bromide

Explanation:
1. Cleavage occurs at the alkyl-oxygen bond because the aryl-oxygen bond is strong: \( \ce{C6H5OH + C2H5Br} \).

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 3: Ether is formed when ethyl alcohol is heated with conc. \( \ce{H2SO4} \). The conditions are
(a) Excess of \( \ce{H2SO4} \) and 170°C
(b) Excess of \( \ce{C2H5OH} \) and 140°C
(c) Excess of \( \ce{C2H5OH} \) and 180°C
(d) Excess of conc. \( \ce{H2SO4} \) and 100°C
Show Answer & Explanation

Answer: (b) Excess of \( \ce{C2H5OH} \) and 140°C

Explanation:
1. Excess alcohol at 413 K favours the ether, whereas excess acid at 443 K favours ethene.

Teacher's Note:
1. Ethers are cleaved by HI, form explosive peroxides in air, and act as Lewis bases forming etherates.
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 4: Addition of alcohols to aldehydes in the presence of anhydrous acids yields
(a) Carboxylic acids
(b) Ethers
(c) Cyclic ethers
(d) Acetals
Show Answer & Explanation

Answer: (d) Acetals

Explanation:
1. The hemiacetal formed first reacts with a second alcohol to give an acetal.

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 5: The ether that undergoes electrophilic substitution reactions is
(a) \( \ce{CH3OC2H5} \)
(b) \( \ce{C6H5OCH3} \)
(c) \( \ce{CH3OCH3} \)
(d) \( \ce{C2H5OC2H5} \)
Show Answer & Explanation

Answer: (b) \( \ce{C6H5OCH3} \)

Explanation:
1. Only anisole has a benzene ring, activated by the OCH3 group.

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 6: Acetyl chloride does not react with
(a) Diethyl ether
(b) Aniline
(c) Phenol
(d) Ethanol
Show Answer & Explanation

Answer: (a) Diethyl ether

Explanation:
1. Aniline, phenol and ethanol are acylated; a simple ether has no active hydrogen.

Teacher's Note:
1. Ethers are cleaved by HI, form explosive peroxides in air, and act as Lewis bases forming etherates.
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 7: The products formed in the reaction \( \ce{C6H5-O-CH3 + HI ->[heat]} \) are
(a) \( \ce{C6H5-I} \) and \( \ce{CH3-OH} \)
(b) \( \ce{C6H5-OH} \) and \( \ce{CH3-I} \)
(c) \( \ce{C6H5-CH3} \) and HOI
(d) \( \ce{C6H6} \) and \( \ce{CH3OI} \)
Show Answer & Explanation

Answer: (b) \( \ce{C6H5-OH} \) and \( \ce{CH3-I} \)

Explanation:
1. The aryl-O bond is not cleaved because of its partial double-bond character, so phenol and methyl iodide form.

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 8: Etherates are
(a) Ethers
(b) Solution in ether
(c) Complexes of ethers with Lewis acid
(d) Complexes of ethers with Lewis base
Show Answer & Explanation

Answer: (c) Complexes of ethers with Lewis acid

Explanation:
1. The oxygen lone pair coordinates with Lewis acids such as \( \ce{BF3} \) or \( \ce{AlCl3} \) (e.g.
2. \( \ce{(C2H5)2O.BF3} \)).

Teacher's Note:
1. Ethers are cleaved by HI, form explosive peroxides in air, and act as Lewis bases forming etherates.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 9: When ether is reacted with \( \ce{O2} \), it undergoes explosion due to
(a) Peroxide
(b) Acid
(c) Ketone
(d) TNT
Show Answer & Explanation

Answer: (a) Peroxide

Explanation:
1. The peroxides formed on standing are explosive when heated or concentrated.

Teacher's Note:
1. Ethers are cleaved by HI, form explosive peroxides in air, and act as Lewis bases forming etherates.
2. Dehydration and substitution with HX both go through carbocations, so 3 degree > 2 degree > 1 degree.

Question 10: The compound which does not react with sodium is
(a) \( \ce{C2H5OH} \)
(b) \( \ce{CH3-O-CH3} \)
(c) \( \ce{CH3COOH} \)
(d) \( \ce{CH3-CHOH-CH3} \)
Show Answer & Explanation

Answer: (b) \( \ce{CH3-O-CH3} \)

Explanation:
1. Dimethyl ether has no acidic hydrogen.

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 11: A substance \( \ce{C4H10O} \) yields on oxidation a compound \( \ce{C4H8O} \) which gives an oxime and a positive iodoform test. The original substance on treatment with conc. \( \ce{H2SO4} \) gives \( \ce{C4H8} \). The structure of the compound is
(a) \( \ce{CH3CH2CH2CH2OH} \)
(b) \( \ce{CH3CH(OH)CH2CH3} \)
(c) \( \ce{(CH3)3COH} \)
(d) \( \ce{CH3CH2-O-CH2CH3} \)
Show Answer & Explanation

Answer: (b) \( \ce{CH3CH(OH)CH2CH3} \)

Explanation:
1. Butan-2-ol is oxidised to butanone (oxime, positive iodoform) and dehydrates to butene.

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 12: Ethylene glycol reacts with excess of \( \ce{PCl5} \) to give
(a) 1,1-Dichloroethane
(b) 1,2-Dichloroethane
(c) 1,1,1-Trichloroethane
(d) 1,1,2,2-Tetrachloroethane
Show Answer & Explanation

Answer: (b) 1,2-Dichloroethane

Explanation:
1. Both OH groups are replaced by Cl: \( \ce{ClCH2CH2Cl} \).

Teacher's Note:
1. PCl5, PBr3 and SOCl2 replace the OH of alcohols by halogen; HX with ZnCl2 does the same via carbocations.
2. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 13: The boiling point of methanol is greater than that of methyl thiol because
(a) There is intramolecular hydrogen bonding in methanol and intermolecular hydrogen bonding in methyl thiol
(b) There is intermolecular hydrogen bonding in methanol and no hydrogen bonding in methyl thiol
(c) There is no hydrogen bonding in methanol and intermolecular hydrogen bonding in methyl thiol
(d) There is intramolecular hydrogen bonding in methanol and no hydrogen bonding in methyl thiol
Show Answer & Explanation

Answer: (b) There is intermolecular hydrogen bonding in methanol and no hydrogen bonding in methyl thiol

Explanation:
1. Oxygen is more electronegative than sulphur, so O-H...O hydrogen bonds exist in methanol but S-H...S bonds are negligible.

Teacher's Note:
1. Hydrogen bonding raises boiling point and solubility, while intramolecular bonding (o-nitrophenol) lowers boiling point.
2. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.

Question 14: In the reaction of glycerol with oxalic acid at 110°C, the product A will be
(a) Glycerol monoformate
(b) Allyl alcohol
(c) Formaldehyde
(d) Acetic acid
Show Answer & Explanation

Answer: (a) Glycerol monoformate

Explanation:
1. The glycerol monooxalate loses \( \ce{CO2} \) to give glycerol monoformate.

Teacher's Note:
1. Glycerol is propane-1,2,3-triol; it gives nitroglycerine, allyl iodide with HI, and acrolein on dehydration.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 15: Which of the following will not form a yellow precipitate on heating with an alkaline solution of iodine?
(a) \( \ce{CH3OH} \)
(b) \( \ce{CH3CH2OH} \)
(c) \( \ce{CH3CH(OH)CH3} \)
(d) \( \ce{CH3CH2CH(OH)CH3} \)
Show Answer & Explanation

Answer: (a) \( \ce{CH3OH} \)

Explanation:
1. Methanol lacks a methyl carbinol group, so it gives no iodoform.

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

Question 16: In Friedel-Crafts acylation, besides \( \ce{AlCl3} \), the other reactants are
(a) Phenol and \( \ce{CH3Cl} \)
(b) Phenol and \( \ce{CH3COCl} \)
(c) Benzene and \( \ce{HN3} \)
(d) Benzene and \( \ce{CH3Cl} \)
Show Answer & Explanation

Answer: (b) Phenol and \( \ce{CH3COCl} \)

Explanation:
1. Acylation uses an acid chloride (here acetyl chloride) with a Lewis acid; \( \ce{CH3Cl} \) would give alkylation.

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 17: At 530 K, glycerol reacts with oxalic acid to produce
(a) Allyl alcohol
(b) Formic acid
(c) Glyceraldehyde
(d) Glycerol monooxalate
Show Answer & Explanation

Answer: (a) Allyl alcohol

Explanation:
1. Heating above 500 K decarboxylates and dehydrates the intermediate to allyl alcohol.

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. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 18: With anhydrous zinc chloride, ethylene glycol gives
(a) Formaldehyde
(b) Acetylene
(c) Acetaldehyde
(d) Acetone
Show Answer & Explanation

Answer: (c) Acetaldehyde

Explanation:
1. Dehydration of glycol gives vinyl alcohol, which tautomerises to ethanal.

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 19: Which of the following compounds gives a yellow precipitate with \( \ce{I2} \) and NaOH?
(a) \( \ce{CH3OH} \)
(b) \( \ce{CH3CH2CH2OH} \)
(c) \( \ce{C2H5OC2H5} \)
(d) \( \ce{CH3CH2OH} \)
Show Answer & Explanation

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

Explanation:
1. Ethanol is oxidised to ethanal, and the \( \ce{CH3CO-} \) group gives iodoform.

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

Question 20: Among the following, HBr reacts fastest with
(a) Propan-1-ol
(b) Propan-2-ol
(c) 2-Methylpropan-1-ol
(d) 2-Methylpropan-2-ol
Show Answer & Explanation

Answer: (d) 2-Methylpropan-2-ol

Explanation:
1. The tertiary alcohol forms the most stable carbocation.

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 21: When phenylmagnesium bromide reacts with tert-butanol, the product would be
(a) Benzene
(b) Phenol
(c) tert-Butylbenzene
(d) tert-Butyl phenyl ether
Show Answer & Explanation

Answer: (a) Benzene

Explanation:
1. The acidic OH protonates the Grignard reagent: \( \ce{C6H5MgBr + (CH3)3COH -> C6H6 + (CH3)3COMgBr} \).

Teacher's Note:
1. Grignard reagents add to carbonyl groups and are destroyed by water, alcohols and acids.
2. Learn the identification tests: Lucas, iodoform, FeCl3, Victor Meyer, Liebermann, bromine water.

Question 22: Dehydration of butan-2-ol yields
(a) 1-Butene
(b) 2-Butene
(c) 2-Butyne
(d) Both (a) and (b)
Show Answer & Explanation

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

Explanation:
1. Loss of water gives 2-butene (major, Saytzeff) and 1-butene (minor).

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 23: Fats on alkaline hydrolysis give
(a) Oils
(b) Soaps
(c) Detergents
(d) Glycol + acid
Show Answer & Explanation

Answer: (b) Soaps

Explanation:
1. Saponification gives soap (sodium salts of fatty acids) and glycerol.

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 24: When the vapours of an alcohol are passed over hot reduced copper, the alcohol that is converted into an alkene quickly is
(a) Primary
(b) Secondary
(c) Tertiary
(d) None of these
Show Answer & Explanation

Answer: (c) Tertiary

Explanation:
1. Tertiary alcohols cannot be dehydrogenated; they dehydrate to alkenes.

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. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 25: A compound of the formula \( \ce{CH3C(OH)3} \), if formed, would give which of the following without reacting with any reagent?
(a) \( \ce{CH3OH} \)
(b) \( \ce{C2H5OH} \)
(c) \( \ce{CH3COOH} \)
(d) HCHO
Show Answer & Explanation

Answer: (c) \( \ce{CH3COOH} \)

Explanation:
1. Three OH groups on one carbon are unstable: it loses water to give acetic acid.

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 26: Which of the following can work as a dehydrating agent for alcohols?
(a) \( \ce{H2SO4} \)
(b) \( \ce{Al2O3} \)
(c) \( \ce{H3PO4} \)
(d) All of these
Show Answer & Explanation

Answer: (d) All of these

Explanation:
1. All three remove water from alcohols to give alkenes or ethers.

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 27: What is formed when glycerol reacts with HI?
(a) 3-Iodopropane-1,2-diol
(b) Allyl iodide
(c) Glyceryl triiodide
(d) Propene oxide
Show Answer & Explanation

Answer: (b) Allyl iodide

Explanation:
1. Glycerol is first converted to 2,3-diiodopropan-1-ol, which loses iodine to give allyl iodide, \( \ce{CH2=CH-CH2I} \).

Teacher's Note:
1. Glycerol is propane-1,2,3-triol; it gives nitroglycerine, allyl iodide with HI, and acrolein on dehydration.
2. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 28: Which alcohol reacts with fatty acids to form fats?
(a) Ethanol
(b) Glycerol
(c) Methanol
(d) Isopropanol
Show Answer & Explanation

Answer: (b) Glycerol

Explanation:
1. Fats are triesters of glycerol with long-chain fatty acids.

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.

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Practice MCQs for JEE Chemistry Alcohols Phenols and Ethers

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