Practice MCQs for JEE Chemistry Alcohols Phenols and Ethers
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Multiple Choice Questions
Assertion (A): Alcoholic fermentation involves conversion of sugar into ethyl alcohol by yeast.
Reason (R): Fermentation involves the slow decomposition of complex organic compounds.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (a) Both A and R are true, and R is the correct explanation of A.
Explanation:
1. Yeast enzymes slowly break down sugars, which is what fermentation means.
Teacher's Note:
1. Fermentation uses enzymes: diastase (starch to maltose), maltase (to glucose) and zymase (to ethanol and CO2).
2. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
Assertion (A): The water solubility of the alcohols follows the order t-butyl > s-butyl alcohol > n-butyl alcohol.
Reason (R): Alcohols form H-bond with water to show soluble nature.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (b) Both A and R are true, but R is not the correct explanation of A.
Explanation:
1. Branching reduces the hydrocarbon surface so solubility increases.
2. The reason is true but it does not explain the order.
Teacher's Note:
1. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
2. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
Assertion (A): Absolute ethanol can be obtained by simple fractional distillation of a mixture of alcohol and water.
Reason (R): The absolute ethanol boils at 78.3°C.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (d) A is false, but R is true.
Explanation:
1. Ethanol and water form an azeotrope (95.6 percent ethanol), so simple distillation cannot give 100 percent ethanol and the assertion is false.
2. The boiling point of absolute ethanol is indeed 78.3°C.
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. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
Assertion (A): Acid catalysed dehydration of t-butanol is slower than n-butanol.
Reason (R): Dehydration involves formation of the protonated alcohol, \( \ce{ROH2+} \).
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (d) A is false, but R is true.
Explanation:
1. Tertiary alcohols dehydrate faster because the tertiary carbocation is more stable, so the assertion is false; protonation is indeed the first step.
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. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
Assertion (A): Tertiary alcohols give turbidity immediately with Lucas reagent.
Reason (R): A mixture of conc. HCl + anhydrous \( \ce{ZnCl2} \) is called Lucas reagent.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (b) Both A and R are true, but R is not the correct explanation of A.
Explanation:
1. Both are true, but the name of the reagent does not explain the fast reaction; the stability of the tertiary carbocation does.
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. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
Assertion (A): 4-Nitrophenol is more acidic than 2,4,6-trinitrophenol.
Reason (R): Phenol is a weaker acid than carbonic acid.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (d) A is false, but R is true.
Explanation:
1. Three nitro groups stabilise the phenoxide much more, so picric acid (pKa 0.4) is far more acidic than 4-nitrophenol (7.15); the assertion is false.
2. The reason is true.
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. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
Assertion (A): Phenols cannot be converted into esters by direct reaction with carboxylic acids.
Reason (R): Electron withdrawing groups increase the acidity of phenols.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (b) Both A and R are true, but R is not the correct explanation of A.
Explanation:
1. Phenols are poor nucleophiles, so acid chlorides or anhydrides are needed.
2. Both statements are true but the reason is unrelated to the assertion.
Teacher's Note:
1. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
2. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
Assertion (A): tert-Butyl alcohol undergoes acid catalysed dehydration readily than propanol.
Reason (R): 3° alcohols do not give Victor Meyer test.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (b) Both A and R are true, but R is not the correct explanation of A.
Explanation:
1. Dehydration is faster because of the stable tertiary carbocation.
2. The Victor Meyer fact is true but is not the reason.
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. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
Assertion (A): The ease of dehydration of alcohols follows the order primary > secondary > tertiary.
Reason (R): Dehydration proceeds through the formation of oxonium ions.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (d) A is false, but R is true.
Explanation:
1. The real order is tertiary > secondary > primary, so the assertion is false.
2. Protonated alcohol (oxonium ion) formation is the first step, so the reason is true.
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. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
Assertion (A): Phenol reacts with acyl halides in the presence of pyridine to form phenyl acetate.
Reason (R): Benzoylation of phenol is carried out in the presence of \( \ce{NH4OH} \).
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (c) A is true, but R is false.
Explanation:
1. Pyridine neutralises the HCl formed, so the assertion is true.
2. Benzoylation (Schotten-Baumann) uses NaOH, not \( \ce{NH4OH} \).
Teacher's Note:
1. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
2. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
Assertion (A): Alcohols are more easily protonated than phenols.
Reason (R): Alcohols undergo intermolecular hydrogen bonding due to the presence of highly electronegative oxygen.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (b) Both A and R are true, but R is not the correct explanation of A.
Explanation:
1. The oxygen lone pair of an alcohol is more available because in phenol it is delocalised into the ring.
2. The reason is true but is not the explanation.
Teacher's Note:
1. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
2. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
Assertion (A): Phenol is less acidic than p-nitrophenol.
Reason (R): Phenolate ion is more stable than p-nitrophenolate ion.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (c) A is true, but R is false.
Explanation:
1. The assertion is true.
2. The nitro group delocalises the charge, so p-nitrophenolate is the more stable ion; the reason is false.
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. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
Assertion (A): Reimer-Tiemann reaction of phenol with \( \ce{CCl4} \) in NaOH at 340 K gives salicylic acid as the major product.
Reason (R): The reaction occurs through intermediate formation of dichlorocarbene.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (c) A is true, but R is false.
Explanation:
1. The assertion is true (the intermediate trichloromethyl group is hydrolysed to COOH)
2. The attacking species with \( \ce{CCl4} \) is not dichlorocarbene in the same way as with chloroform, so the reason is not correct.
Teacher's Note:
1. Reimer-Tiemann reaction formylates phenol at the ortho position through dichlorocarbene; with CCl4 it gives salicylic acid.
2. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
Assertion (A): Primary alcohols can be distinguished by Victor Meyer's test.
Reason (R): Primary alcohols with nitrolic acid dissolve in NaOH to form a blood red colour but secondary alcohols form pseudonitroles which give blue colouration with NaOH.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (a) Both A and R are true, and R is the correct explanation of A.
Explanation:
1. The test uses the different products formed by the three classes (nitrolic acid, pseudonitrole, no reaction) with HNO2 and NaOH, which explains how primary alcohols are identified.
Teacher's Note:
1. Nitro groups at ortho and para positions increase the acidity of phenol, and ortho-nitrophenol is steam volatile.
2. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
Assertion (A): \( \ce{HIO4} \) cleaves 1,2-glycols but not 1,3- or higher glycols.
Reason (R): Only 1,2-glycols form cyclic esters which subsequently undergo cleavage to form carbonyl compounds.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (a) Both A and R are true, and R is the correct explanation of A.
Explanation:
1. The cyclic periodate ester can form only with adjacent OH groups; its breakdown gives carbonyl compounds.
Teacher's Note:
1. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
2. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
Assertion (A): Dehydration of glycerol with \( \ce{KHSO4} \) gives acrolein.
Reason (R): Acrolein is an alpha,beta-unsaturated aldehyde.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (b) Both A and R are true, but R is not the correct explanation of A.
Explanation:
1. Loss of two molecules of water gives \( \ce{CH2=CH-CHO} \)
2. The reason is true but describes the product, it does not explain the dehydration.
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. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
Assertion (A): Both symmetrical and unsymmetrical ethers can be prepared by Williamson's synthesis.
Reason (R): Williamson's synthesis is an example of a nucleophilic substitution reaction.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (b) Both A and R are true, but R is not the correct explanation of A.
Explanation:
1. Any alkoxide and primary alkyl halide can be combined.
2. The reason is true but does not explain why both types are accessible.
Teacher's Note:
1. Williamson synthesis is an SN2 reaction of an alkoxide with a primary alkyl halide; tertiary halides eliminate.
2. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
Assertion (A): Etherates are coordination complexes of ethers with Lewis acids.
Reason (R): Ethers are easily cleaved by mineral acids such as HCl and \( \ce{H2SO4} \) at 373 K.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (c) A is true, but R is false.
Explanation:
1. Etherates such as ether-\( \ce{BF3} \) exist.
2. Ethers are cleaved by HI or HBr, not easily by dilute HCl or \( \ce{H2SO4} \), so the reason is false.
Teacher's Note:
1. Ethers are cleaved by HI, form explosive peroxides in air, and act as Lewis bases forming etherates.
2. Decide separately whether the assertion and reason are true, then ask whether the reason really explains the assertion.
Assertion (A): tert-Butyl methyl ether is not prepared by the reaction of tert-butyl bromide with sodium methoxide.
Reason (R): Sodium methoxide is a strong nucleophile.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation
Answer: (b) Both A and R are true, but R is not the correct explanation of A.
Explanation:
1. The tertiary halide gives elimination (isobutene) with methoxide.
2. The reason is true but the key factor is that methoxide is also a strong base.
Teacher's Note:
1. Ethers are cleaved by HI, form explosive peroxides in air, and act as Lewis bases forming etherates.
2. Test statements about acidity or dehydration with the stability of the intermediate ion or carbocation.
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