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JEE Advanced Previous Year Questions (2018 - 2023): Alcohols, Phenols and Ethers | Chemistry for JEE Main & Advanced PDF Download
2023
Q1: In the given reaction scheme, P is a phenyl alkyl ether, Q is an aromatic compound; R and S are the major products.
The correct statement about S is :
(a) It primarily inhibits noradrenaline degrading enzymes.
(b) It inhibits the synthesis of prostaglandin.
(c) It is a narcotic drug.
(d) It is ortho-acetylbenzoic acid. [JEE Advanced 2023 Paper 1]
Ans: (b) 
It inhibit synthesis of noradrenaline degrading enzymes.
Q2: Consider the following reaction scheme and choose the correct option(s) for the major products Q, R and S. 
(a) 
(b) 
(c) 
(d) 
[JEE Advanced 2023 Paper 1]
Ans: (b)
2020
Q1: An organic compound (C8H10O2) rotates plane-porarised light. It produces pink color with neutral FeCl3 solution. What is the total number of all the possible isomers for this compound? [JEE Advanced 2020 Paper 2]
Ans: 6
Phenolic (−OH) group gives positive test with neutral FeCl3 solution, means organic compound (C8H10O2) also rotate plane porarised light means compound is an optically active and chiral carbon atom is present.
So, the possible structures which are optically active and have phenolic group are as followed :
Therefore, total optically active isomers will be 6.
Q2: In the reaction scheme shown below Q, R and S are the major products.
The correct structure of
(a) S is 
(b) Q is 
(c) R is 
(d) S is 
[JEE Advanced 2020 Paper 1]
Ans: (b) & (d)
Compound (P) undergoes Friedel-Craft acylation reaction in presence of succinic anhydride and AlCl3 to gives an acid (Q).
Compound (Q) on treatment with Zn-Hg/HCl undergoes Clemmensen reduction, where ketone group change into alkane and on further reaction with dehydrating agent H3PO4 gives compound (R).
Compound (R) on reaction with Grignard reagent and heated in presence of acid gives dehydrating product (S).
Thus, the option (b) and (d) are correct.
2018
Q1: LIST-I contains reactions and LIST-II contains major products.
Match the reaction in LIST-I with one or more products in LIST-II and choose the correct option.
(a) P − 1,5;Q − 2;R − 3;S − 4
(b) P − 1,4;Q − 2;R − 4;S − 3
(c) P − 1,4;Q − 1,2;R − 3,4;S − 4
(d) P −4 ,5;Q − 4;R − 4;S − 3,4 [JEE Advanced 2018 Paper 2]
Ans: (b)
P. Reactant 1 , acts as a base and abstracts hydrogen from β carbon of tert butyl bromide halide (reactant 2 ) forming an alkene and an alcohol.
Elimination proceeds via E2 mechanism. Substitution of reactant 1 is not possible on reactant 2 due to steric crowding at 2.
Q. Reactant 1 (tert butoxide) acts as a base and abstracts proton from acid (HBr) forming an alcohol and methyl bromide.
Ans: (b)
P. Reactant 1 , acts as a base and abstracts hydrogen from β carbon of tert butyl bromide halide (reactant 2 ) forming an alkene and an alcohol.
Elimination proceeds via E2 mechanism. Substitution of reactant 1 is not possible on reactant 2 due to steric crowding at 2.
Q. Reactant 1 (tert butoxide) acts as a base and abstracts proton from acid (HBr) forming an alcohol and methyl bromide.
R. Sodium methoxide ( NaOMe) is a strong base and abstracts proton from β carbon of tert Butyl with simultaneous less of bromide ion forming an alkene.
S. Reactant 1 (tert-butoxide) acts as a nucleophile and attacks from the backside of methyl bromide, with subsequent removal of bromide ion. This is an SN2 mechanism.
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FAQs on JEE Advanced Previous Year Questions (2018 - 2023): Alcohols, Phenols and Ethers - Chemistry for JEE Main & Advanced
| 1. What are alcohols, phenols, and ethers? |  |
Ans. Alcohols, phenols, and ethers are organic compounds that contain oxygen atoms bonded to carbon atoms. Alcohols have a hydroxyl (-OH) group attached to a carbon atom, phenols have a hydroxyl group attached to an aromatic ring, and ethers have an oxygen atom bonded to two carbon atoms.
| 2. What are some common properties of alcohols, phenols, and ethers? | |
Ans. Alcohols, phenols, and ethers have different physical and chemical properties. Alcohols and phenols can form hydrogen bonds, making them soluble in water. Ethers, on the other hand, have weaker intermolecular forces and are less soluble in water. Alcohols and phenols can undergo various reactions, such as oxidation, dehydration, and esterification.
| 3. How are alcohols, phenols, and ethers named? | |
Ans. Alcohols are named by replacing the -e at the end of the alkane name with -ol. Phenols are named by adding the suffix -ol to the name of the parent aromatic compound. Ethers are named by naming the two alkyl or aryl groups bonded to the oxygen atom, followed by the word "ether."
| 4. What are some uses of alcohols, phenols, and ethers? | |
Ans. Alcohols have various uses, such as as solvents, antiseptics, and fuels. Phenols are used as disinfectants, antiseptics, and in the production of plastics and pharmaceuticals. Ethers are commonly used as solvents and as anesthetic agents in medicine.
| 5. How can alcohols, phenols, and ethers be distinguished in a chemical reaction? | |
Ans. Alcohols can be distinguished from phenols and ethers by their reactivity with oxidizing agents. Alcohols can be oxidized to form aldehydes, ketones, or carboxylic acids, while phenols do not undergo oxidation easily. Ethers do not show any significant reactivity with oxidizing agents. Additionally, alcohols and phenols can be distinguished by their acidity, with phenols being more acidic due to the resonance stabilization of the phenoxide ion.
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