Which of the following arrangements with respect to their reactivity in nucleophilic addition reaction is correct?

Q: Which of the following arrangements with respect to their reactivity in nucleophilic addition reaction is correct?

Reactivity in nucleophilic addition reactions is governed by a combination of **steric hindrance** and **electronic effects** around the electrophilic carbonyl carbon: 1. Ketones are significantly less reactive than aldehydes due to the bulkiness and electron-donating inductive effect (+I) of their two alkyl/aryl groups. Thus, **acetophenone** has the lowest reactivity. 2. For substituted benzaldehydes, electron-withdrawing groups heighten the partial positive charge on the carbonyl carbon, acce

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Q jee_main_2024_01_february_morning Reactions of Carbonyl Compounds

Match List - I with List - II.

List - I (Reactions)	List - II (Reagents)
(A) $CH₃(CH₂)₅-CO-OC₂H₅ arrow CH₃(CH₂)₅CHO$	(I) $CH₃MgBr, H₂O$ $CH_3MgBr, H_2O$
(B) $C₆H₅COC₆H₅ arrow C₆H₅CH₂C₆H₅$	(II) $Zn(Hg)$ $Zn(Hg)$ and conc. $HCl$ $HCl$
(C) $C₆H₅CHO arrow C₆H₅CH(OH)CH₃$	(III) $NaBH₄, H^+$ $NaBH_4, H^+$
(D) $CH₃COCH₂COOC₂H₅ arrow CH₃CH(OH)CH₂COOC₂H₅$	(IV) DIBAL-H, $H₂O$ $H_2O$

Choose the correct answer from options given below:

A. $A-(III), (B)-(IV), (C)-(I), (D)-(II)$
B. $A-(IV), (B)-(II), (C)-(I), (D)-(III)$
C. $A-(IV), (B)-(II), (C)-(III), (D)-(I)$
D. $A-(III), (B)-(IV), (C)-(II), (D)-(I)$

Solution

Core Logic

Let's analyze the transformation happening in each reaction:

(A) $CH₃(CH₂)₅COOC₂H₅ arrow CH₃(CH₂)₅CHO$ An ester is reduced to an aldehyde. This is a selective reduction achieved using DIBAL-H (Diisobutylaluminium hydride) followed by hydrolysis. Thus, (A) $arrow$ $\rightarrow$ (IV).

(B) $C₆H₅COC₆H₅ arrow C₆H₅CH₂C₆H₅$ A ketone (carbonyl group $>C=O$ $>C=O$) is fully reduced to an alkane ( $>CH₂$ $>CH_2$) methylene group. This is the Clemmensen reduction, which uses Zinc amalgam and concentrated HCl. Thus, (B) $arrow$ $\rightarrow$ (II).

(C) $C₆H₅CHO arrow C₆H₅CH(OH)CH₃$ Benzaldehyde (aldehyde) is converted into a secondary alcohol with an extra methyl group. This is a nucleophilic addition of a Grignard reagent ( $CH₃MgBr$ $CH_3MgBr$) followed by hydrolysis. Thus, (C) $arrow$ $\rightarrow$ (I).

(D) $CH₃COCH₂COOC₂H₅ arrow CH₃CH(OH)CH₂COOC₂H₅$ A ketone group is reduced to a secondary alcohol while the ester group remains intact. $NaBH₄$ $NaBH_4$ is a mild reducing agent that reduces aldehydes and ketones but generally does not touch esters. Thus, (D) $arrow$ $\rightarrow$ (III).

Pattern Recognition

Ester $arrow$ $\rightarrow$ Aldehyde = DIBAL-H Ketone $arrow$ $\rightarrow$ Alkane = Clemmensen ( $Zn(Hg)/HCl$ $Zn(Hg)/HCl$) or Wolff-Kishner Carbonyl $arrow$ $\rightarrow$ Alcohol with carbon chain extension = Grignard Reagent Ketone $arrow$ $\rightarrow$ Alcohol (leaving ester intact) = $NaBH₄$ $NaBH_4$

Chapter Mix

Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids

Q jee_main_2024_29_jan_morning Reactions of Carbonyl Compounds

The final product A formed in the following multistep reaction sequence is

Reactions of Carbonyl Compounds diagram for Q77 - JEE Main 2024 Morning — A reaction sequence starting with styrene undergoing Markovnikov hydration, followed by oxidation with CrO3, and finally reduction with hydrazine and KOH.

A.
B.
C.
D.

Solution

Core Logic

The reaction sequence proceeds in three distinct steps from the starting material, styrene ( $Ph-CH=CH₂$ $Ph-CH=CH_2$).

Step 1: Acid-catalyzed Hydration Styrene reacts with $H₂O, H^+$ $H_2O, H^+$ to undergo electrophilic addition. Protonation yields the more stable secondary benzylic carbocation. Attack by water followed by deprotonation gives 1-phenylethanol ( $Ph-CH(OH)-CH₃$ $Ph-CH(OH)-CH_3$).

Step 2: Oxidation 1-phenylethanol is a secondary alcohol. Treatment with chromium trioxide ( $CrO₃$ $CrO_3$, Jones reagent condition) oxidizes the secondary alcohol to a ketone. This yields acetophenone ( $Ph-CO-CH₃$ $Ph-CO-CH_3$).

Step 3: Wolff-Kishner Reduction Acetophenone is treated with hydrazine ( $NH₂-NH₂$ $NH_2-NH_2$) and a strong base ( $KOH$ $KOH$) under heating. This is the classic Wolff-Kishner reduction, which completely reduces the carbonyl group ( $C=O$ $C=O$) to a methylene group ( $-CH₂-$ $-CH_2-$). The final product is ethylbenzene ( $Ph-CH₂-CH₃$ $Ph-CH_2-CH_3$).

Step 1: Overall Reaction Pathway

The final product A is ethylbenzene.

Chapter Mix

Class 11 Chemistry: Hydrocarbons Class 12 Chemistry: Alcohols Phenols and Ethers Class 12 Chemistry: Aldehydes Ketones and Carboxylic Acids

Q jee_main_2024_29_jan_morning Chemical Reactions of Aldehydes and Ketones

From the compounds given below, number of compounds which give positive Fehling's test is _____. Benzaldehyde, Acetaldehyde, Acetone, Acetophenone, Methanal, 4-nitrobenzaldehyde, cyclohexane carbaldehyde.

Numerical Answer. Answer: 3 to 3

Solution

Core Logic

Fehling's test is a mild oxidizing test used primarily to distinguish aliphatic aldehydes from ketones and aromatic aldehydes.

Aliphatic aldehydes (like methanal, acetaldehyde, cyclohexane carbaldehyde) give a positive Fehling's test (formation of red-brown precipitate of $Cu₂O$ $Cu_2O$).
Aromatic aldehydes (like benzaldehyde, 4-nitrobenzaldehyde) lack alpha-hydrogens in a purely aliphatic environment and are not sufficiently easily oxidized to give a positive Fehling's test.
Ketones (like acetone, acetophenone) generally do not give a positive Fehling's test (except $α$ $\alpha$-hydroxy ketones).

Step 1: Evaluation of Given Compounds

Benzaldehyde: Aromatic aldehyde $arrow$ $\rightarrow$ Negative
Acetaldehyde ( $CH₃CHO$ $CH_3CHO$): Aliphatic aldehyde $arrow$ $\rightarrow$ Positive
Acetone: Ketone $arrow$ $\rightarrow$ Negative
Acetophenone: Ketone $arrow$ $\rightarrow$ Negative
Methanal ( $HCHO$ $HCHO$): Aliphatic aldehyde $arrow$ $\rightarrow$ Positive
4-nitrobenzaldehyde: Aromatic aldehyde $arrow$ $\rightarrow$ Negative
Cyclohexane carbaldehyde: Aliphatic aldehyde $arrow$ $\rightarrow$ Positive

The compounds giving a positive test are Acetaldehyde, Methanal, and Cyclohexane carbaldehyde.

Pattern Recognition

Tollens' reagent oxidizes ALL aldehydes (aliphatic + aromatic). Fehling's reagent is weaker and only oxidizes ALIPHATIC aldehydes.

Chapter Mix

Class 12 Chemistry: Aldehydes Ketones and Carboxylic Acids

Q jee_main_2024_30_january_evening Cannizzaro Reaction

m-chlorobenzaldehyde on treatment with

50%

KOH solution yields

A.
B.
C.
D.

Solution

Core Logic

m-chlorobenzaldehyde lacks alpha-hydrogen atoms. Therefore, when treated with concentrated base like $50%$ $50\%$ KOH, it undergoes a disproportionation redox reaction known as the Cannizzaro reaction.

Two molecules of the aldehyde react: one gets oxidized to the corresponding carboxylate ion (m-chlorobenzoate ion), and the other gets reduced to the corresponding alcohol (m-chlorobenzyl alcohol).

Step 1: Reaction

The reaction proceeds as:

Cannizzaro reaction of m-chlorobenzaldehyde diagram for Q64 - JEE Main 2024 Evening

Pattern Recognition

No $α$ $\alpha$-hydrogen + Conc. Alkali ( $50%$ $50\%$ KOH/NaOH) = Cannizzaro (Oxidation to salt of carboxylic acid + Reduction to primary alcohol).

Chapter Mix

Class 12 Chemistry: Aldehydes Ketones and Carboxylic Acids

Q jee_main_2024_30_jan_morning Preparation of Aldehydes

This reduction reaction is known as:

Preparation of Aldehydes diagram for Q62 - JEE Main 2024 Morning — The image shows the catalytic hydrogenation of benzoyl chloride to benzaldehyde in the presence of Pd-BaSO4.

A. $Rosenmund reduction$ $\text{Rosenmund reduction}$
B. $Wolff-Kishner reduction$ $\text{Wolff-Kishner reduction}$
C. $Stephen reduction$ $\text{Stephen reduction}$
D. $Etard reduction$ $\text{Etard reduction}$

Solution

Related Formula

R-COCl + H₂ Pd/BaSO₄ R-CHO + HCl

Core Logic

The reaction depicts the partial reduction of an acid chloride (benzoyl chloride) to an aldehyde (benzaldehyde) using hydrogen gas in the presence of a poisoned palladium catalyst (Pd supported on $BaSO₄$ $BaSO_4$).

Preparation of Aldehydes solution diagram for Q62 - JEE Main 2024 Morning — The image shows the catalytic hydrogenation of benzoyl chloride to benzaldehyde in the presence of Pd-BaSO4.

This specific reaction is known as the Rosenmund reduction.

Pattern Recognition

Acid Chloride + $H₂, Pd/BaSO₄$ $H_2, Pd/BaSO_4$ $arrow$ $\rightarrow$ Aldehyde is strictly the Rosenmund reduction. The $BaSO₄$ $BaSO_4$ poisons the catalyst to prevent over-reduction to an alcohol.

Chapter Mix

Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids

Which of the following arrangements with respect to their reactivity in nucleophilic addition reaction is correct?

Solution & Explanation

Core Logic

Pattern Recognition

Chapter Mix

Reference Study Guides

More Aldehydes, Ketones and Carboxylic Acids Previous-Year Questions — Page 8

Solution

Core Logic

Pattern Recognition

Chapter Mix

Solution

Core Logic

Step 1: Overall Reaction Pathway

Chapter Mix

Solution

Core Logic

Step 1: Evaluation of Given Compounds

Pattern Recognition

Chapter Mix

Solution

Core Logic

Step 1: Reaction

Pattern Recognition

Chapter Mix

Solution

Related Formula

Core Logic

Pattern Recognition

Chapter Mix

More Aldehydes, Ketones and Carboxylic Acids Questions — jee_main_2025_24_jan_morning

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