Join WhatsApp Icon JEE WhatsApp Group
Question 44

The total number of chiral molecules formed from one molecule of P on complete ozonolysis (O$$_3$$, Zn/H$$_2$$O) is _______.

image


Correct Answer: 2

The structure of compound P is pent-3-en-2-ol, $$CH_3CH=CHCH(OH)CH_3$$. It contains one carbon-carbon double bond and one hydroxyl (-OH) group.

Step 1 (Cleavage of the C=C bond)
Under complete ozonolysis followed by reductive work-up (O$$\_3$$, Zn/H$$\_2$$O), every carbon of the C=C bond is converted into a carbonyl centre. Hence

$$CH_3CH=CHCH(OH)CH_3 \xrightarrow[H_2O]{O_3/Zn} CH_3CHO + CH_3CH(OH)CHO$$

Therefore, one molecule of P gives two organic fragments:

• Acetaldehyde, $$CH_3CHO$$ (achiral, because the carbonyl carbon is attached to two identical atoms—oxygen on one side and nothing else asymmetric).
• 2-Hydroxypropanal, $$CH_3CH(OH)CHO$$.

Step 2 (Checking chirality of each product)

For acetaldehyde there is no stereogenic (asymmetric) carbon, so it is achiral.

In 2-hydroxypropanal the middle carbon (shown in bold) $$CH_3\mathbf{C}H(OH)CHO$$ is attached to four different groups: $$CH_3$$, $$H$$, $$OH$$ and $$CHO$$. Thus it is a stereogenic centre and the molecule exists as two non-superimposable mirror images (enantiomers), labelled R and S.

Step 3 (Total count of distinct chiral molecules)

Because 2-hydroxypropanal forms one pair of enantiomers, the number of different chiral molecules obtained from a single molecule of P is 2.

Hence, the total number of chiral molecules produced is 2.

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