Join WhatsApp Icon JEE WhatsApp Group
Question 50

Match the reactions in List-I with the features of their products in List-II and choose the correct option.

List-IList-II
(P)(-)-1-Bromo-2-ethylpentane (single enantiomer) $$\xrightarrow[S_N2 \text{ reaction}]{\text{aq. NaOH}}$$(1)Inversion of configuration
(Q)(-)-2-Bromopentane (single enantiomer) $$\xrightarrow[S_N2 \text{ reaction}]{\text{aq. NaOH}}$$(2)Retention of configuration
(R)(-)-3-Bromo-3-methylhexane (single enantiomer) $$\xrightarrow[S_N1 \text{ reaction}]{\text{aq. NaOH}}$$(3)Mixture of enantiomers
(S)
image
(4)Mixture of structural isomers
(5)Mixture of diastereomers

The given reactions involve substitution of bromine by the $$OH^{-}$$ ion. Whether the product keeps, inverts or partially loses the original configuration depends on (i) the mechanism ($$S_N2$$ or $$S_N1$$) and (ii) the position of the stereogenic centre(s) in the molecule.

Case P : $$(-)\text{-1-Bromo-2-ethylpentane}\xrightarrow[S_N2]{aq.\,NaOH}$$

• In $$S_N2$$ the attack is backside and therefore the carbon that bears the leaving group undergoes inversion. 
• Here the leaving group is on C-1, which is not a stereogenic centre (it is $$CH_2Br$$). 
• The only stereogenic centre is C-2. Because that carbon is not touched during the reaction, its configuration is retained.
Hence the optical purity of the starting material is preserved: the product shows retention of configuration.

⇒ P → (2)

Case Q : $$(-)\text{-2-Bromopentane}\xrightarrow[S_N2]{aq.\,NaOH}$$

• The bromine is on the stereogenic C-2. 
• An $$S_N2$$ displacement on this carbon forces backside attack and gives one step inversion. 
Therefore the configuration is converted into the opposite enantiomer: the product shows inversion of configuration.

⇒ Q → (1)

Case R : $$(-)\text{-3-Bromo-3-methylhexane}\xrightarrow[S_N1]{aq.\,NaOH}$$

• C-3 is tertiary; ionisation of $$C-Br$$ gives a planar carbocation. 
• Nucleophilic attack by $$OH^{-}$$ is equally probable from either face. 
• No other stereogenic centre is present. Thus the product is obtained as an equal (50 : 50) pair of enantiomers, i.e. a racemic mixture.

⇒ R → (3)

Case S : (The substrate possesses the leaving group on one stereogenic centre and contains at least one more untouched stereogenic centre.) In an $$S_N1$$ process the reacting centre racemises while the remote centre retains its configuration. Consequently the product set contains stereoisomers that are not mirror images but differ in the configuration of only one of the centres — they are diastereomers.

⇒ S → (5)

Collecting all matches:
P → 2; Q → 1; R → 3; S → 5

Therefore the correct option is
Option B which is: P → 2; Q → 1; R → 3; S → 5

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