Join WhatsApp Icon JEE WhatsApp Group
Question 57

The major product (P) in the following reaction is:

image

The starting material is phenylglyoxal, $$\text{Ph-C(=O)-CHO},$$ which is an $\alpha$-ketoaldehyde. It contains two carbonyl groups but does not possess any $\alpha$-hydrogen atoms.

The reaction is carried out in the presence of $$KOH$$ and heat $$\Delta.$$

When an aldehyde lacking $\alpha$-hydrogens is treated with a strong base, it undergoes the Cannizzaro reaction. Since phenylglyoxal contains both an aldehyde and a ketone group within the same molecule, it undergoes an intramolecular Cannizzaro reaction.

In a Cannizzaro reaction, one carbonyl group is oxidized while the other is reduced. Here, the aldehyde portion is oxidized to a carboxylate ion, whereas the ketone portion is reduced to an alcohol.

The mechanism proceeds as follows:

  1. The hydroxide ion $$OH^-$$ attacks the more electrophilic and less sterically hindered aldehyde carbonyl carbon.
  2. The resulting alkoxide intermediate undergoes a hydride shift. The negatively charged oxygen reforms the carbonyl group, causing the adjacent hydrogen atom to migrate as a hydride ion $$H^-$$ to the neighboring ketone carbonyl carbon.
  3. This produces a carboxylate group and an alkoxide ion. A rapid proton transfer then converts the alkoxide into a secondary alcohol while the oxidized portion remains as the potassium carboxylate salt.

Thus,

  • the aldehyde group $$-CHO$$ is converted into $$-COO^-K^+,$$
  • and the ketone group $$-C(=O)-$$ is converted into $$-CH(OH)-.$$

The final product obtained is potassium mandelate, having the structure

$$\boxed{\text{Ph-CH(OH)-COO}^-,\text{K}^+.}$$

Therefore, the correct answer is

$$\boxed{\text{Option (B).}}$$

Get AI Help

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