JEE Chemistry Alcohols Phenols and Ethers MCQs Set 21

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Chapter-wise Objective Questions: Alcohols Phenols and Ethers

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Multiple Choice Questions

Question 1: Which of the following reactions would produce a secondary alcohol?
(a) \( \ce{C6H5COCH3} \) with \( \ce{CH3MgBr} \), then \( \ce{H+} \)
(b) \( \ce{C6H5COCH3} \) with \( \ce{LiAlH4} \), then \( \ce{H+} \)
(c) \( \ce{CH3CHO} \) with \( \ce{LiAlH4} \), then \( \ce{H+} \)
(d) \( \ce{CH3COCH3} \) with \( \ce{OH-} \), then \( \ce{Br2} \)
Show Answer & Explanation

Answer: (b) \( \ce{C6H5COCH3} \) with \( \ce{LiAlH4} \), then \( \ce{H+} \)

Explanation:
1. A ketone reduced by LiAlH4 gives a secondary alcohol (1-phenylethanol)
2. Grignard addition to a ketone gives a tertiary alcohol; reduction of an aldehyde gives a primary alcohol.

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 2: On reaction with hot conc. \( \ce{H2SO4} \), which one of the following compounds loses a molecule of water?
(a) \( \ce{CH3COCH3} \)
(b) \( \ce{CH3COOH} \)
(c) \( \ce{CH3OCH3} \)
(d) \( \ce{CH3CH2OH} \)
Show Answer & Explanation

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

Explanation:
1. Ethanol is dehydrated to 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. Hydrogen bonding explains most physical trends: boiling point, solubility and volatility of ethers, ortho-nitrophenol.

Question 3: The best method to prepare cyclohexene from cyclohexanol is by using
(a) Conc. HCl + \( \ce{ZnCl2} \)
(b) Conc. \( \ce{H3PO4} \)
(c) HBr
(d) Conc. HCl
Show Answer & Explanation

Answer: (b) Conc. \( \ce{H3PO4} \)

Explanation:
1. Phosphoric acid dehydrates without a competing nucleophilic anion; HCl and HBr would give the alkyl halide.

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 4: Which of the following compounds is most acidic?
(a) \( \ce{CH4} \)
(b) \( \ce{C2H6} \)
(c) \( \ce{CH#CH} \)
(d) \( \ce{C2H5OH} \)
Show Answer & Explanation

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

Explanation:
1. Ethanol (pKa about 16) is more acidic than ethyne (about 25), ethane (about 50) and methane (about 48).

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 5: A compound that does not react with 2,4-dinitrophenylhydrazine and Na is
(a) Acetone
(b) Acetaldehyde
(c) \( \ce{CH3OH} \)
(d) \( \ce{CH2=CHOCH3} \)
Show Answer & Explanation

Answer: (d) \( \ce{CH2=CHOCH3} \)

Explanation:
1. Carbonyl compounds react with 2,4-DNP and alcohols react with Na; methyl vinyl ether has neither a C=O nor an O-H.

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 6: Which of the following reactions is correctly represented?
(a) 3-Methylanisole + HBr gives 3-methylphenol + \( \ce{CH3Br} \)
(b) 3-Methylanisole + HBr gives 3-bromotoluene + \( \ce{CH3OH} \)
(c) 3-Methylanisole + HBr gives 3-bromoanisole + \( \ce{CH4} \)
(d) 3-Methylanisole + HBr gives no cleavage of the ether
Show Answer & Explanation

Answer: (a) 3-Methylanisole + HBr gives 3-methylphenol + \( \ce{CH3Br} \)

Explanation:
1. In alkyl aryl ethers HBr cleaves the alkyl-oxygen bond, giving the phenol and the alkyl halide.
2. The aryl-oxygen bond is too strong to break.

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 7: Tertiary butyl alcohol gives tertiary butyl chloride on treatment with
(a) Conc. HCl / anhydrous \( \ce{ZnCl2} \)
(b) KCN
(c) NaOCl
(d) \( \ce{Cl2} \)
Show Answer & Explanation

Answer: (a) Conc. HCl / anhydrous \( \ce{ZnCl2} \)

Explanation:
1. Lucas reagent converts tertiary alcohols to chlorides by an SN1 route.

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 8: Phenol reacts with benzenediazonium chloride in a basic medium to give
(a) p-Hydroxyazobenzene
(b) Diphenyl ether
(c) Biphenyl
(d) 4-Hydroxybiphenyl
Show Answer & Explanation

Answer: (a) p-Hydroxyazobenzene

Explanation:
1. Azo coupling at the para position of phenoxide gives \( \ce{C6H5-N=N-C6H4-OH} \).

Teacher's Note:
1. Diazonium salts give phenol on warming with water and azo dyes by coupling with phenols and amines.
2. Compare acidity through the stability of the conjugate base: electron-withdrawing groups strengthen the acid, electron-donating groups weaken it.

Question 9: The reaction of phenol with chloroform and sodium hydroxide to give o-hydroxybenzaldehyde involves the formation of
(a) Dichlorocarbene
(b) Trichlorocarbene
(c) Chlorine atoms
(d) Chlorine molecules
Show Answer & Explanation

Answer: (a) Dichlorocarbene

Explanation:
1. Chloroform and base give \( \ce{:CCl2} \), the electrophile.

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 10: Glycerol is used in the manufacture of
(a) Dynamite
(b) Varnish
(c) Paints
(d) Soft drinks
Show Answer & Explanation

Answer: (a) Dynamite

Explanation:
1. Glycerol trinitrate (nitroglycerine) is the main constituent of dynamite.

Teacher's Note:
1. Glycerol is propane-1,2,3-triol; it gives nitroglycerine, allyl iodide with HI, and acrolein on dehydration.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 11: Glycerol as a triester is present in
(a) Petroleum
(b) Kerosene
(c) Vegetable oil and fat
(d) Naphtha
Show Answer & Explanation

Answer: (c) Vegetable oil and fat

Explanation:
1. Fats and oils are triglycerides.

Teacher's Note:
1. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 12: In the presence of air, fermentation of ethyl alcohol by azotobacter bacteria forms
(a) \( \ce{CH2=CH2} \)
(b) \( \ce{C2H6} \)
(c) \( \ce{CH3CHO} \)
(d) \( \ce{CH3COOH} \)
Show Answer & Explanation

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

Explanation:
1. Bacterial oxidation of ethanol gives acetic acid (vinegar).

Teacher's Note:
1. Fermentation uses enzymes: diastase (starch to maltose), maltase (to glucose) and zymase (to ethanol and CO2).
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 13: Substances used in bringing down the temperature in high fevers are called
(a) Pyretics
(b) Antipyretics
(c) Antibiotics
(d) Antiseptics
Show Answer & Explanation

Answer: (b) Antipyretics

Explanation:
1. Antipyretics, such as paracetamol and aspirin, lower fever.

Teacher's Note:
1. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.
2. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.

Question 14: When glycol is heated with a dicarboxylic acid, the products are
(a) Polyesters
(b) Polyethers
(c) Polyethylene
(d) No reaction at all
Show Answer & Explanation

Answer: (a) Polyesters

Explanation:
1. A diol with a diacid gives a polyester (e.g. terylene from terephthalic acid).

Teacher's Note:
1. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 15: Phenol is used in the manufacture of
(a) Bakelite
(b) Polystyrene
(c) Nylon
(d) PVC
Show Answer & Explanation

Answer: (a) Bakelite

Explanation:
1. Phenol with formaldehyde gives Bakelite.

Teacher's Note:
1. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.
2. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.

Question 16: Power alcohol is
(a) An alcohol of 95 percent purity
(b) A mixture of petrol hydrocarbons and ethanol
(c) Rectified spirit
(d) A mixture of methanol and ethanol
Show Answer & Explanation

Answer: (b) A mixture of petrol hydrocarbons and ethanol

Explanation:
1. Power alcohol is ethanol blended with petrol and used as motor fuel.

Teacher's Note:
1. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 17: Alcoholic fermentation is brought about by the action of
(a) \( \ce{CO2} \)
(b) \( \ce{O2} \)
(c) Invertase
(d) Yeast
Show Answer & Explanation

Answer: (d) Yeast

Explanation:
1. Yeast supplies the zymase complex that converts sugars to ethanol.

Teacher's Note:
1. Fermentation uses enzymes: diastase (starch to maltose), maltase (to glucose) and zymase (to ethanol and CO2).
2. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.

Question 18: Rectified spirit is a mixture of
(a) 95 percent ethyl alcohol + 5 percent water
(b) 94 percent ethyl alcohol + 6 percent water
(c) 94.4 percent ethyl alcohol + 5.43 percent water
(d) 95.57 percent ethyl alcohol + 4.43 percent water
Show Answer & Explanation

Answer: (d) 95.57 percent ethyl alcohol + 4.43 percent water

Explanation:
1. The azeotrope contains 95.57 percent ethanol by mass (4.43 percent water).

Teacher's Note:
1. Ethanol and water form an azeotrope with 95.6 percent alcohol; absolute alcohol needs benzene (azeotropic distillation) or quicklime and further drying.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 19: Glycerol is used
(a) As a sweetening agent
(b) In the manufacture of good quality soap
(c) In the manufacture of nitroglycerine
(d) In all of the above
Show Answer & Explanation

Answer: (d) In all of the above

Explanation:
1. Glycerol is used in all these applications.

Teacher's Note:
1. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 20: Glycerol is not used in which of the following cases?
(a) Explosive making
(b) Shaving soap making
(c) As an antifreeze for water
(d) As an antiseptic agent
Show Answer & Explanation

Answer: (d) As an antiseptic agent

Explanation:
1. Glycerol is an ingredient of explosives (nitroglycerine), soaps and antifreeze mixtures, but it is not an antiseptic.

Teacher's Note:
1. Glycerol is propane-1,2,3-triol; it gives nitroglycerine, allyl iodide with HI, and acrolein on dehydration.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 21: In order to make alcohol undrinkable, pyridine and methanol are added to it. The resulting alcohol is called
(a) Power alcohol
(b) Proof spirit
(c) Denatured spirit
(d) Poison alcohol
Show Answer & Explanation

Answer: (c) Denatured spirit

Explanation:
1. Denatured spirit has additives that make it unfit to drink.

Teacher's Note:
1. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.
2. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.

Question 22: Denatured spirit is mainly used as a
(a) Good fuel
(b) Drug
(c) Solvent in preparing varnishes
(d) Material in the preparation of oil
Show Answer & Explanation

Answer: (c) Solvent in preparing varnishes

Explanation:
1. Denatured spirit is used as a solvent for varnishes and paints.

Teacher's Note:
1. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 23: The main constituent of dynamite is
(a) Nitrobenzene
(b) Nitroglycerine
(c) Picric acid
(d) TNT
Show Answer & Explanation

Answer: (b) Nitroglycerine

Explanation:
1. Dynamite is nitroglycerine absorbed in kieselguhr.

Teacher's Note:
1. Glycerol is propane-1,2,3-triol; it gives nitroglycerine, allyl iodide with HI, and acrolein on dehydration.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 24: Wine (alcoholic beverages) contains
(a) \( \ce{CH3OH} \)
(b) Glycerol
(c) \( \ce{C2H5OH} \)
(d) 2-Propanol
Show Answer & Explanation

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

Explanation:
1. Wine contains ethanol (about 10 to 15 percent).

Teacher's Note:
1. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 25: Widespread deaths due to liquor poisoning occur due to
(a) Presence of carbonic acid in liquor
(b) Presence of ethyl alcohol in liquor
(c) Presence of methyl alcohol in liquor
(d) Presence of lead compounds in liquor
Show Answer & Explanation

Answer: (c) Presence of methyl alcohol in liquor

Explanation:
1. Methanol is highly toxic.

Teacher's Note:
1. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 26: Diethyl ether finds use in medicine as
(a) A pain killer
(b) An antiseptic
(c) A hypnotic
(d) An anaesthetic
Show Answer & Explanation

Answer: (d) An anaesthetic

Explanation:
1. Ether was widely used as a general anaesthetic.

Teacher's Note:
1. Ethers are cleaved by HI, form explosive peroxides in air, and act as Lewis bases forming etherates.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 27: A washing soap can be prepared by saponification with alkali of
(a) Rose oil
(b) Groundnut oil
(c) Paraffin oil
(d) Kerosene
Show Answer & Explanation

Answer: (b) Groundnut oil

Explanation:
1. Only vegetable or animal fats and oils (glyceryl esters) saponify; rose oil, paraffin oil and kerosene do not.

Teacher's Note:
1. Link every compound with its use: ethanol in tonics and power alcohol, glycerol in nitroglycerine, glycol as antifreeze, ether as anaesthetic.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

Question 28: Ether can be used
(a) As a general anaesthetic
(b) As a refrigerant
(c) In perfumery
(d) All of these
Show Answer & Explanation

Answer: (d) All of these

Explanation:
1. Ether is used as an anaesthetic, a refrigerant and a solvent for perfumes.

Teacher's Note:
1. Ethers are cleaved by HI, form explosive peroxides in air, and act as Lewis bases forming etherates.
2. Methanol is poisonous; denatured spirit is ethanol made unfit to drink.

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