JEE Main 2023 — Chemistry Organic Chemistry

2023integerhard

A trisubstituted compound ' $A$ ', ${C}_{10}{H}_{12}{O}_{2}$ gives neutral ${\mathrm{FeCl}}_{3}$ test positive. Treatment of compound ' $A$ ' with $\mathrm{NaOH}$ and ${\mathrm{CH}}_{3}\mathrm{Br}$ gives ${C}_{11}{H}_{14}{O}_{2}$ , with hydroiodic acid gives methyl iodide and with hot conc. $\mathrm{NaOH}$ gives a compound $B$ , ${C}_{10}{H}_{12}{O}_{2}$ . Compound ' $A$ ' also decolorises alkaline ${\mathrm{KMnO}}_{4}$ . The number of $\pi$ bond/s present in the compound ' $A$ ' is _____ .

Official previous-year question

Held on 30 Jan 2023 · Verified 6 Jul 2026.

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Solution

The trisubstituted compound ' $A$ ', ${C}_{10}{H}_{12}{O}_{2}$ gives neutral ${\mathrm{FeCl}}_{3}$ test positive, means the compound is phenol. Phenol on treatment with $\mathrm{NaOH}$ and ${\mathrm{CH}}_{3}\mathrm{Br}$ gives ${C}_{10}{H}_{11}{O}_{2}{\mathrm{CH}}_{3}$ . The given compound is reacting with hot conc. $\mathrm{NaOH}$ gives a compound $B$ , ${C}_{10}{H}_{12}{O}_{2}$ . The reaction is Cannizzaro's reaction. Hence, compound must be benzaldehyde derivative. Compound ' $A$ ' also decolourises alkaline ${\mathrm{KMnO}}_{4}$ , means compound contains an alkyl group attached to benzene ring. Hence, the structure of the compound can be written as follows,

JEE Main 2023 Chemistry, Carboxylic Acid Derivatives — solution figure 1

The reactions are shown below.

JEE Main 2023 Chemistry, Carboxylic Acid Derivatives — solution figure 2

JEE Main 2023 Chemistry, Carboxylic Acid Derivatives — solution figure 3

JEE Main 2023 Chemistry, Carboxylic Acid Derivatives — solution figure 4

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Consider the following reaction sequence ![JEE Main 2026 Chemistry, Alcohols Phenols and Ethers — question figure](https://prepforbharat.s3.ap-south-1.amazonaws.com/exam/615f0e999476412f48314daf/Chemistry/images/Alcohols_Phenols_and_Ethers/6983c1ad8bfdbb24356397bb/question_1__q_6983c1ad8bfdbb24356397bb__cdn-question-pool.getmarks.app__28S1_q_52_1_v2__2fe787b06d_final_ppt_sync.png) Compound $(\mathrm{y})$ develops characteristic colour with neutral $\mathrm{FeCl}_{3}$ solution. Identify the INCORRECT statement from the following for the above sequence.

2026medium

Given below are two statements: Statement I: Benzene is nitrated to give nitrobenzene, which on further treatment with $\mathrm{CH}_{3} \mathrm{COCl} / \mathrm{AlCl}_{3}$ will give ![JEE Main 2026 Chemistry, Hydrocarbons — question figure](https://prepforbharat.s3.ap-south-1.amazonaws.com/exam/615f0e999476412f48314daf/Chemistry/images/Hydrocarbons/6983c1898bfdbb24356395fc/question_1__q_6983c1898bfdbb24356395fc__cdn-question-pool.getmarks.app__22S1_q_54_1__65f8139d89_final_ppt_sync.png) Statement II: $-\mathrm{NO}_{2}$ group is a $m$-directing, and deactivating group. In the light of the above statements, choose the most appropriate answer from the options given below

2026medium

Given below are two statements: Statement I: $\left(\mathrm{CH}_{3}\right)_{3} \stackrel{\oplus}{\mathrm{C}}$ is more stable than $\stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{3}$ as nine hyperconjugation interactions are possible in $\left(\mathrm{CH}_{3}\right)_{3} \stackrel{\oplus}{\mathrm{C}}$. Statement II: $\stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{3}$ is less stable than $\left(\mathrm{CH}_{3}\right)_{3} \stackrel{\oplus}{\mathrm{C}}$ as only three hyperconjugation interactions are possible in $\stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{3}$. In the light of the above statements, choose the correct answer from the options given below

2026medium

Which of the following reactions is an example of Wurtz reaction?

2026easy

A hydroxy compound $(\mathrm{X})$ with molar mass $122 \mathrm{~g} \mathrm{~mol}^{-1}$ is acetylated with acetic anhydride, using a large excess of the reagent ensuring complete acetylation of all hydroxyl groups. The product obtained has a molar mass of $290 \mathrm{~g} \mathrm{~mol}^{-1}$. The number of hydroxyl groups present in compound (X) is:

2026medium

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Solution

JEE Main 2023 Chemistry, Carboxylic Acid Derivatives — solution figure 1

The reactions are shown below.

JEE Main 2023 Chemistry, Carboxylic Acid Derivatives — solution figure 2

JEE Main 2023 Chemistry, Carboxylic Acid Derivatives — solution figure 3

JEE Main 2023 Chemistry, Carboxylic Acid Derivatives — solution figure 4

JEE Main 2023 — Chemistry Organic Chemistry

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JEE Main Organic Chemistry in other years

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JEE Main 2023 — Chemistry Organic Chemistry

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Solution

Your note

JEE Main Organic Chemistry in other years

More JEE Main Organic Chemistry questions

Other Chemistry topics for JEE Main

Physical Chemistry

Inorganic Chemistry

Keep practicing Organic Chemistry