A molecule ("P") on treatment with acid undergoes rearrangement and gives ("Q") ("Q") on ozonolysis followed by reflux under alkaline condition gives ("R"). The structure of ("R") is given below:
Rearrangement and Ozonolysis product diagram for Q33 - JEE Main 2025 Morning
The image displays the chemical structure of product R obtained from rearrangement and subsequent reaction steps.
The structure of (mathbfPi^prime primemathbfP^prime prime) is

Solution & Explanation

### Core Logic The reaction sequence indicates that molecule "P" undergoes an acid-catalyzed rearrangement to produce alkene/alcohol intermediate "Q". Subsequent ozonolysis breaks down the double bond system, and alkaline reflux sets up an intramolecular aldol condensation sequence to form the cyclic ketone system "R". Following the detailed ring contraction/expansion step templates outlined below:
Mechanism sequence step for Q33 - JEE Main 2025 Morning
The image displays the chemical structure of product R obtained from rearrangement and subsequent reaction steps.
Mechanism sequence step for Q33 - JEE Main 2025 Morning
The image displays the chemical structure of product R obtained from rearrangement and subsequent reaction steps.
Mechanism sequence step for Q33 - JEE Main 2025 Morning
The image displays the chemical structure of product R obtained from rearrangement and subsequent reaction steps.
Mechanism sequence step for Q33 - JEE Main 2025 Morning
The image displays the chemical structure of product R obtained from rearrangement and subsequent reaction steps.
Mechanism sequence step for Q33 - JEE Main 2025 Morning
The image displays the chemical structure of product R obtained from rearrangement and subsequent reaction steps.
Mechanism sequence step for Q33 - JEE Main 2025 Morning
The image displays the chemical structure of product R obtained from rearrangement and subsequent reaction steps.
Mechanism sequence step for Q33 - JEE Main 2025 Morning
The image displays the chemical structure of product R obtained from rearrangement and subsequent reaction steps.
Mechanism sequence step for Q33 - JEE Main 2025 Morning
The image displays the chemical structure of product R obtained from rearrangement and subsequent reaction steps.
### Pattern Recognition Sees: Acidic rearrangement rightarrow ozonolysis rightarrow intramolecular aldol condensation. Shortcut: Work backwards from the dicarbonyl fragments formed after opening the final product ring system. ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids

Reference Study Guides

More Aldehydes, Ketones and Carboxylic Acids Previous-Year Questions — Page 3

Q jee_main_2025_04_april_evening Iodoform Test
Which among the following compounds give yellow solid when reacted with NaOI/NaOH? (A) CH_3 - CH(OH) - C_2H_5 (B) CH_3 - CH_2 - CH_2 - OH (C) CH_3 - CO - C_2H_5 (D) CH_3-CO- OH (E) CH_3 - CH_2 - CHO Choose the correct answer from the options given below:
  • A. (B), (C) and (E) Only
  • B. (A) and (C) Only
  • C. (C) and (D) Only
  • D. (A), (C) and (D) Only

Solution

### Related Formula textCompounds with CH_3-CH(OH)- text or CH_3-CO- text groups undergo the iodoform reaction to form CHI_3 downarrow text (Yellow Solid) ### Core Logic Let's check the structural groups of each given option: - **(A)** CH_3 - CH(OH) - C_2H_5: Contains the methylcarbinol group (CH_3-CH(OH)-). Gives a positive iodoform test. - **(B)** CH_3 - CH_2 - CH_2 - OH: Linear primary alcohol, does not contain the required group. - **(C)** CH_3 - CO - C_2H_5: Contains the methyl ketone group (CH_3-CO-). Gives a positive iodoform test. - **(D)** CH_3 - OH: Methanol does not give the test. - **(E)** CH_3 - CH_2 - H: Ethane does not give the test. Thus, only **(A)** and **(C)** yield the yellow precipitate of iodoform (CHI_3). ### Step 1: Chemical Equations The balanced haloform pathways occur as follows: CH_3-CH(OH)-CH_2-CH_3 xrightarrowtextNaOI/NaOH CHI_3downarrow + textCH_3text-CH_2text-COO^-textNa^+ CH_3-CO-CH_2-CH_3 xrightarrowtextNaOI/NaOH CHI_3downarrow + textCH_3text-CH_2text-COO^-textNa^+ ### Pattern Recognition The iodoform test specifically isolates methyl ketones or secondary methyl alcohols. Scan dynamically for a terminal -CH_3 affixed directly to a carbonyl oxygen index (C=O) or a hydroxyl carbon (CH-OH). ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids Class 12 Chemistry: Alcohols, Phenols and Ethers
Q29 jee_main_2025_04_april_morning Aldol Condensation
Aldol condensation is a popular and classical method to prepare alpha, beta-unsaturated carbonyl compounds. This reaction can be both intermolecular and intramolecular. Predict which one of the following is not a product of intramolecular aldol condensation?
  • A. textProduct 1
  • B. textProduct 2
  • C. textProduct 3
  • D. textProduct 4

Solution

### Core Logic Intramolecular aldol condensation involves a dicarbonyl compound reacting within itself to yield stable cyclic alpha, beta-unsaturated rings (most commonly 5- or 6-membered rings due to minimal ring strain). * Products (1), (2), and (3) can all be cleanly synthesized via intramolecular cyclization path workflows from their respective dialdehyde/diketone precursors. * Product (4) features an exo-cyclic group structure arrangement formed strictly through an **intermolecular** condensation sequence step between two distinct reactant units, rather than an internal cyclization path layout. ### Pattern Recognition Look closely at the ring substitution system. Intermolecular steps are forced when intramolecular cyclization path workflows would generate highly strained small rings or structurally impossible orientations. ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids
Q41 jee_main_2025_04_april_morning Chemical Properties of Ketones
An organic compound (X) with molecular formula C_3H_6O is not readily oxidised. On reduction it gives C_3H_8O (Y) which reacts with HBr to give a bromide (Z) which is converted to Grignard reagent. This Grignard reagent on reaction with (X) followed by hydrolysis gives 2, 3-dimethylbutan-2-ol. Compounds (X), (Y) and (Z) respectively are:
  • A. mathrmCH_3mathrmCOCH_3, mathrmCH_3mathrmCH_2mathrmCH_2mathrmOH, mathrmCH_3mathrmCH(Br)CH_3
  • B. mathrmCH_3mathrmCOCH_3, mathrmCH_3mathrmCH(OH)CH_3, mathrmCH_3mathrmCH(Br)CH_3
  • C. mathrmCH_3mathrmCH_2mathrmCHO, mathrmCH_3mathrmCH_2mathrmCH_2mathrmOH, mathrmCH_3mathrmCH_2mathrmCH_2mathrmBr
  • D. mathrmCH_3mathrmCH_2mathrmCHO, mathrmCH_3mathrmCH=CH_2, mathrmCH_3mathrmCH(Br)CH_3

Solution

### Core Logic Let's deduce the identities stepwise: 1. Compound (X) has the formula C_3H_6O and is resistant to mild oxidation, which identifies it as a ketone: **Acetone** (CH_3COCH_3). 2. Reduction of Acetone yields a secondary alcohol, Propan-2-ol (CH_3CH(OH)CH_3, Compound Y). 3. Treatment of Propan-2-ol with HBr substitutes the hydroxyl group to form 2-Bromopropane (CH_3CH(Br)CH_3, Compound Z). 4. Reacting 2-Bromopropane with Magnesium in ether creates the branched Grignard reagent, Isopropylmagnesium bromide ((CH_3)_2CHMgBr). 5. Finally, nucleophilic addition of this Grignard reagent to Acetone followed by aqueous workup yields the highly branched tertiary alcohol: **2,3-dimethylbutan-2-ol**. ### Pattern Recognition Resistance to mild oxidation immediately distinguishes ketones from isomeric aldehydes. Nucleophilic addition of an isopropyl Grignard to acetone cleanly yields the 2,3-dimethylbutan-2-ol framework. ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids Class 12 Chemistry: Alcohols, Phenols and Ethers
Q30 jee_main_2025_07_april_evening Identification of Carbonyl Compounds
"P" is an optically active compound with molecular formula textC_6textH_12textO. When "P" is treated with 2,4-dinitrophenylhydrazine, it gives a positive test. However, in presence of Tollens reagent, "P" gives a negative test. Predict the structure of "P".
  • A. textCH_3text-C(=textO)text-CH_2text-CH_2text-CH_2text-CH_3
  • B. textCH_3text-C(=textO)text-CH(textCH_2text-CH_3)text-CH_3
  • C. textH-C(=textO)text-CH_2text-CH(textCH_2text-CH_3)text-CH_3
  • D. textCH_3text-C(=textO)text-CH_2text-CH(textCH_3)_2

Solution

### Related Formula textCarbonyl compound + text2,4-DNP ightarrow textHydrazone derivative (Positive test) textAldehyde + textTollens' Reagent ightarrow textSilver Mirror (Positive test) textKetone + textTollens' Reagent ightarrow textNo reaction (Negative test) ### Core Logic Analyzing individual functional constraints: - Positive 2,4-DNP test shows compound contains a carbonyl group (aldehyde or ketone). - Negative Tollens' test clarifies it is not an aldehyde; hence it must be a ketone. - The compound is optically active, meaning it must possess a chiral center (carbon with 4 distinct groups). Let's evaluate the options via structural configurations:
Identification of Carbonyl Compounds diagram for Q30 - JEE Main 2025 Evening
Identification of Carbonyl Compounds diagram for Q30 - JEE Main 2025 Evening
Identification of Carbonyl Compounds diagram for Q30 - JEE Main 2025 Evening
Identification of Carbonyl Compounds diagram for Q30 - JEE Main 2025 Evening
### Step 1: Structural Verification Option (2) represents 3-methylpentan-2-one: textCH3-textC(=textO)-oversetasttextCH(textCH3)(textCH2textCH3) The third carbon (C3) is linked to: -textH, -textCH_3, -textCH_2textCH_3, and -textCOCH_3. It has 4 distinct structural fields, making it chiral and optically active. ### Pattern Recognition Tollens' negative + DNP positive = Ketone. Once categorized as a ketone, look directly for the structure holding a carbon with four unique groups to secure the optical activity constraint. ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids Class 11 Chemistry: Organic Chemistry - Some Basic Principles and Techniques
Q42 jee_main_2025_24_jan_evening Preparation of Aldehydes
Match List-I with List-II
List-IList-II (Name of Reaction)
(A) mathrmRCN xrightarrow[text(ii)mathrmH_3mathrmO^+]text(i)mathrmSnCl_2, mathrmHCl mathrmRCHO(I) Etard reaction
(B)
Preparation of Aldehydes diagram for Q42 - JEE Main 2025 Evening
The Match List displays chemical transformations side-by-side with their respective named organic chemical reactions.
(II) Gatterman-Koch reaction
(C)
Preparation of Aldehydes diagram for Q42 - JEE Main 2025 Evening
The Match List displays chemical transformations side-by-side with their respective named organic chemical reactions.
(III) Rosenmund reduction
(D)
Preparation of Aldehydes diagram for Q42 - JEE Main 2025 Evening
The Match List displays chemical transformations side-by-side with their respective named organic chemical reactions.
(IV) Stephen reaction
Choose the correct answer from the options given below:
  • A. \text{(A)-(IV), (B)-(III), (C)-(I), (D)-(II)}
  • B. \text{(A)-(III), (B)-(IV), (C)-(II), (D)-(I)}
  • C. \text{(A)-(I), (B)-(III), (C)-(II), (D)-(IV)}
  • D. \text{(A)-(III), (B)-(IV), (C)-(I), (D)-(II)}

Solution

### Core Logic Let's match each aldehyde preparation method with its official named organic reaction: * **(A) mathrmRCN ightarrow mathrmRCHO using mathrmSnCl_2/mathrmHCl followed by hydrolysis:** This is the classic **Stephen reaction** ightarrow **(IV)**. * **(B) Reducing an acyl chloride (mathrmRCOCl) to an aldehyde using mathrmH_2 over mathrmPd-BaSO_4:** This partial reduction is known as the **Rosenmund reduction** ightarrow **(III)**. * **(C) Oxidizing toluene to benzaldehyde using chromyl chloride (mathrmCrO_2mathrmCl_2) in mathrmCS_2:** This selective oxidation method is the **Etard reaction** ightarrow **(I)**. * **(D) Converting benzene to benzaldehyde using mathrmCO and mathrmHCl in the presence of anhydrous mathrmAlCl_3/mathrmCuCl:** This formylation process is the **Gatterman-Koch reaction** ightarrow **(II)**. Combining these assignments yields the final sequence: (A)-(IV), (B)-(III), (C)-(I), (D)-(II). ### Step-by-Step Layout The visual reaction components correspond directly to the official structural transformations:
Preparation of Aldehydes solution diagram for Q42 - JEE Main 2025 Evening
The Match List displays chemical transformations side-by-side with their respective named organic chemical reactions.
Preparation of Aldehydes solution diagram for Q42 - JEE Main 2025 Evening
The Match List displays chemical transformations side-by-side with their respective named organic chemical reactions.
Preparation of Aldehydes solution diagram for Q42 - JEE Main 2025 Evening
The Match List displays chemical transformations side-by-side with their respective named organic chemical reactions.
### Pattern Recognition Quick identification keys: - Nitrile ightarrow Aldehyde = Stephen - Acid Chloride ightarrow Aldehyde = Rosenmund - Toluene ightarrow Chromyl Complex = Etard - Benzene ightarrow Carbon Monoxide = Gatterman-Koch ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids

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