Join WhatsApp Icon JEE WhatsApp Group
Question 47

An organic compound P having molecular formula $$C_6H_6O_3$$ gives ferric chloride test and does not have intramolecular hydrogen bond. The compound P reacts with 3 equivalents of $$NH_2OH$$ to produce oxime Q. Treatment of P with excess methyl iodide in the presence of KOH produces compound R as the major product. Reaction of R with excess iso-butylmagnesium bromide followed by treatment with $$H_3O^+$$ gives compound S as the major product.

The total number of methyl ($$-CH_3$$) group(s) in compound S is ______.


Correct Answer: 12

Step 1: Identification of Compound P

  • Molecular Formula: $$\text{C}_6\text{H}_6\text{O}_3$$
  • Ferric Chloride ($$\text{FeCl}_3$$) Test: Indicates the presence of phenolic or enolic hydroxyl ($$-\text{OH}$$) groups.
  • No Intramolecular Hydrogen Bonding: This rules out adjacent arrangements like pyrogallol ($$1,2,3$$-trihydroxybenzene).

Consequently, compound $$P$$ is phloroglucinol ($$1,3,5$$-trihydroxybenzene). Phloroglucinol readily exhibits keto-enol tautomerism to exist in its keto form, cyclohexane-$$1,3,5$$-trione. Because it has $$3$$ carbonyl groups in this form, it reacts perfectly with $$3$$ equivalents of hydroxylamine ($$\text{NH}_2\text{OH}$$) to yield the trioxime Q.

Step 2: Formation of Compound R

When phloroglucinol ($$P$$) is treated with excess methyl iodide ($$\text{CH}_3\text{I}$$) in the presence of a strong base like $$\text{KOH}$$, it undergoes exhaustive C-alkylation at its active methylene positions rather than O-alkylation.

Each of the three $$-\text{CH}_2-$$ positions in the cyclohexane-$$1,3,5$$-trione tautomer is methylated twice, leading to $$2,2,4,4,6,6$$-hexamethylcyclohexane-$$1,3,5$$-trione as compound $$R$$.

  • Methyl groups in $$R$$: $$6$$ methyl groups attached directly to the ring carbons.

Step 3: Formation of Compound S

Compound $$R$$ contains $$3$$ ketone carbonyl groups. When treated with excess iso-butylmagnesium bromide ($$\text{i-BuMgBr}$$, a Grignard reagent) followed by acid hydrolysis ($$\text{H}_3\text{O}^+$$), each carbonyl carbon undergoes a nucleophilic addition reaction to form a tertiary alcohol.

  • Each ketone group adds one iso-butyl group ($$-\text{CH}_2-\text{CH}(\text{CH}_3)_2$$).
  • Since there are $$3$$ ketone groups, a total of $$3$$ iso-butyl groups are added.

Step 4: Total Methyl Group Count in S

Let's add up all the methyl ($$-\text{CH}_3$$) groups present in the final structure $$S$$:

  • From the core structure of $$R$$: $$6 \text{ methyl groups}$$
  • From the $$3$$ attached iso-butyl groups: $$3 \times 2 = 6 \text{ methyl groups}$$

$$\text{Total number of methyl groups} = 6 + 6 = 12$$

Get AI Help

Create a FREE account and get:

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

JEE Quant Questions | JEE Quantitative Ability

JEE DILR Questions | LRDI Questions For JEE

JEE Verbal Ability Questions | VARC Questions For JEE

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