Join WhatsApp Icon JEE WhatsApp Group
Question 43

Identify (A) in the following reaction sequence:

image
  • Step 1: Grignard Addition to Ketone (A → Tertiary Alcohol)

    Compound A contains both an alkene group and a methyl ketone group ($$\text{--C}(=\text{O})\text{CH}_3$$). When treated with methylmagnesium bromide ($$\text{CH}_3\text{MgBr}$$) followed by acid workup ($$\text{H}^+/\text{H}_2\text{O}$$), the nucleophilic Grignard reagent selectively attacks the carbonyl carbon of the ketone to yield a tertiary alcohol containing a $$-\text{C}(\text{OH})(\text{CH}_3)_2$$ group.


  • Step 2: Acid-Catalyzed Cyclization / Dehydration (Formation of B)

    Treating the tertiary alcohol intermediate with concentrated sulfuric acid and heat ($$\text{Con. H}_2\text{SO}_4/\Delta$$) leads to protonation of the hydroxyl group followed by the loss of water ($$-\text{H}_2\text{O}$$) to form a stable carbocation. This carbocation undergoes an intramolecular electrophilic aromatic substitution (Friedel-Crafts alkylation-type cyclization) with the adjacent alkene/aromatic network, closing into a stable indene-like fused five-membered ring structure B.


  • Step 3: Reductive Ozonolysis Verification

    Subjecting the cyclic alkene B to ozonolysis ($$\text{O}_3, \text{Zn}/\text{H}_2\text{O}$$) oxidatively cleaves the newly formed ring double bond, generating the dicarbonyl compound shown at the top left containing both a formyl ($$-\text{CHO}$$) and an acetyl ($$-\text{COCH}_3$$) group, fully validating the carbon skeleton of A.

Conclusion:

Compound A is an ortho-substituted benzene derivative containing a 1-propenyl side chain and a methyl ketone side chain, which undergoes nucleophilic addition followed by dehydration-cyclization.

Answer: Structure (A) as shown in the reaction scheme.

Get AI Help

Video Solution

video

Create a FREE account and get:

  • Free JEE Mains Previous Papers PDF
  • Take JEE Mains paper tests

Free JEE Topicwise Questions

JEE Rotational MotionJEE Units & MeasurementsJEE Atomic StructureJEE GravitationJEE Periodic Table & PeriodicityJEE StatisticsJEE Inverse Trigonometric FunctionsJEE Magnetism & Magnetic MaterialsJEE Sequences & SeriesJEE MatricesJEE Alternating CurrentsJEE Carboxylic AcidsJEE Permutations & CombinationsJEE Work, Energy & PowerJEE Electromagnetic InductionJEE Electronic DevicesJEE d and f-Block ElementsJEE Chemical KineticsJEE Heat TransferJEE Three Dimensional GeometryJEE Magnetic Effects of CurrentJEE Hydrocarbons - AromaticJEE Electromagnetic WavesJEE Aldehydes & KetonesJEE Hydrocarbons - AlkanesJEE Applications of DerivativesJEE EquilibriumJEE Indefinite IntegrationJEE Chemical ThermodynamicsJEE ElectrochemistryJEE ProbabilityJEE BiomoleculesJEE Continuity & DifferentiabilityJEE Kinetic Theory of GasesJEE Vector AlgebraJEE Hydrocarbons - AlkynesJEE Differential EquationsJEE Current & ResistanceJEE Straight LinesJEE WavesJEE Redox ReactionsJEE Hydrocarbons - AlkenesJEE DeterminantsJEE SolutionsJEE Ray OpticsJEE Dual Nature of Matter & RadiationJEE Chemical Bonding & Molecular StructureJEE Complex NumbersJEE Sets, Relations & FunctionsJEE Electric Charges & FieldsJEE Laws of MotionJEE Fluid MechanicsJEE Basic Concepts in ChemistryJEE Trigonometric FunctionsJEE LimitsJEE Laws of ThermodynamicsJEE Kinematics - 2D MotionJEE p-Block Elements (Groups 13-18)JEE Simple Harmonic MotionJEE Electric Potential & CapacitanceJEE Coordination CompoundsJEE JEE 2D GeometryJEE CirclesJEE Definite IntegrationJEE EMF & Circuit AnalysisJEE Surface TensionJEE Atoms & NucleiJEE Laboratory Experiments - XIJEE Number SystemJEE Basic Principles of Organic ChemistryJEE Wave OpticsJEE Quadratic EquationsJEE Alcohols, Phenols & EthersJEE Organic Compounds with HalogensJEE DifferentiationJEE Conic SectionsJEE Nitrogen-Containing CompoundsJEE ElasticityJEE Practical Organic ChemistryJEE Kinematics - 1D MotionJEE Purification & CharacterisationJEE Binomial Theorem
Ask AI