Join WhatsApp Icon JEE WhatsApp Group
Question 68

'x' is the product which is obtained &om propanenitrile and stannous chloride in the presence of hydrochloric acid followed by hydrolysis. 'y' is the product which is obtained from the but-2-ene by the ozonolysis followed by hydrolysis. From the followu1g, which product is not obtained when one mole of 'x' and one mole of 'y' react with, each other in the presence of alkali followed by heating?

We first identify the products $$x$$ and $$y$$.

Finding x: Propanenitrile ($$CH_3CH_2CN$$) is treated with stannous chloride ($$SnCl_2$$) and hydrochloric acid, followed by hydrolysis. This is the Stephen reduction, which converts a nitrile to an aldehyde. Therefore $$x = \text{propanal}\;(CH_3CH_2CHO)$$.

Finding y: But-2-ene ($$CH_3CH{=}CHCH_3$$) undergoes ozonolysis followed by hydrolysis. The double bond is cleaved to produce two molecules of ethanal (acetaldehyde, $$CH_3CHO$$). Since we take one mole of the ozonolysis product, $$y = \text{ethanal}\;(CH_3CHO)$$.

When one mole of propanal and one mole of ethanal react in the presence of alkali followed by heating, aldol condensation followed by dehydration takes place. Four $$\alpha,\beta$$-unsaturated aldehyde products are possible:

Product 1 — Self-aldol of ethanal: The enolate of one ethanal molecule attacks the carbonyl of another ethanal. After dehydration this gives $$CH_3CH{=}CHCHO$$, which is but-2-enal (crotonaldehyde).

Product 2 — Cross-aldol (ethanal enolate + propanal): The enolate of ethanal ($${}^{-}CH_2CHO$$) attacks the carbonyl carbon of propanal. The resulting aldol product dehydrates to give $$CH_3CH_2CH{=}CHCHO$$ = pent-2-enal.

Product 3 — Cross-aldol (propanal enolate + ethanal): The enolate of propanal ($$CH_3\overset{-}{C}HCHO$$) attacks the carbonyl carbon of ethanal. The aldol product dehydrates to give $$CH_3CH{=}C(CH_3)CHO$$ = 2-methylbut-2-enal.

Product 4 — Self-aldol of propanal: The enolate of one propanal attacks the carbonyl of another propanal. Dehydration gives $$CH_3CH_2CH{=}C(CH_3)CHO$$ = 2-methylpent-2-enal.

Now consider the options. 3-Methylbut-2-enal has the structure $$(CH_3)_2C{=}CHCHO$$. Forming this would require a branched reactant such as acetone or isobutyraldehyde as one of the starting materials, but neither is present in our reaction mixture. Therefore, 3-methylbut-2-enal cannot be obtained from this reaction.

Hence, the correct answer is Option 2.

Get AI Help

Create a FREE account and get:

  • Free JEE Mains Previous Papers PDF
  • Take JEE Mains 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