JEE Challenger
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Reaction Scheme Involving Lactone Reduction and Subsequent Reactions

With reference to the scheme given, which of the given statment(s) about T,U,V\mathbf{T}, \mathbf{U}, \mathbf{V} and W\mathbf{W} is (are) correct ?

Question Diagram 1

Options

A

T\mathbf{T} is soluble in hot aqueous NaOH\mathrm{NaOH}

Correct
B

U\mathbf{U} is optically active

C

Molecular formula of W\mathbf{W} is C10H18O4\mathrm{C}_{10}\mathrm{H}_{18}\mathrm{O}_4

Correct
D

V\mathbf{V} gives effervescence on treatment with aqueous NaHCO3\mathrm{NaHCO}_3

Correct

Step-by-Step Solution

To determine the correct statements about compounds T,U,V,\mathbf{T}, \mathbf{U}, \mathbf{V}, and W\mathbf{W}, we analyze each step in the given reaction sequence:

1. Analysis of Compound T\mathbf{T} and Option A

  • Compound T\mathbf{T} is a δ\delta-lactone (a cyclic ester), specifically 4-methyltetrahydro-2H-pyran-2-one with molecular formula C6H10O2\mathrm{C}_6\mathrm{H}_{10}\mathrm{O}_2.
  • When heated with aqueous NaOH\mathrm{NaOH}, lactones undergo base-catalyzed hydrolysis (saponification) to form the sodium salt of a hydroxy carboxylic acid: T+NaOH(aq)→ΔHO−CH2−CH2−CH(CH3)−CH2−COONa\mathbf{T} + \mathrm{NaOH(aq)} \xrightarrow{\Delta} \mathrm{HO-CH_2-CH_2-CH(CH_3)-CH_2-COONa}
  • The ionic sodium hydroxycarboxylate salt is highly polar and water-soluble. Thus, T\mathbf{T} is soluble in hot aqueous NaOH\mathrm{NaOH}.
  • Option A is correct.

2. Reduction of T\mathbf{T} to U\mathbf{U} and Option B

  • Reduction of the lactone T\mathbf{T} using lithium aluminium hydride (LiAlH4\mathrm{LiAlH}_4) cleaves the cyclic ester linkage to yield a primary diol U\mathbf{U}: T→LiAlH4U:HO−CH2−CH2−CH(CH3)−CH2−CH2−OH\mathbf{T} \xrightarrow{\mathrm{LiAlH}_4} \mathbf{U} : \mathrm{HO-CH_2-CH_2-CH(CH_3)-CH_2-CH_2-OH}
  • Compound U\mathbf{U} is 3-methylpentane-1,5-diol.
  • The central carbon (C-3\mathrm{C\text{-}3}) is attached to a hydrogen atom, a methyl group (− ⁣CH3\mathrm{-\!CH_3}), and two identical −CH2CH2OH-\mathrm{CH_2CH_2OH} chain segments.
  • Due to the presence of two identical substituents on C-3\mathrm{C\text{-}3}, the molecule possesses a plane of symmetry, making it achiral and optically inactive.
  • Option B is incorrect.

3. Formation of W\mathbf{W} and Option C

  • Treatment of diol U\mathbf{U} with excess acetic anhydride, (CH3CO)2O(\mathrm{CH}_3\mathrm{CO})_2\mathrm{O}, acetylates both hydroxyl groups to give the diacetate ester W\mathbf{W}: U→excess (CH3CO)2OW:CH3COO−CH2−CH2−CH(CH3)−CH2−CH2−OCOCH3\mathbf{U} \xrightarrow{\text{excess }(\mathrm{CH}_3\mathrm{CO})_2\mathrm{O}} \mathbf{W} : \mathrm{CH_3COO-CH_2-CH_2-CH(CH_3)-CH_2-CH_2-OCOCH_3}
  • Counting the atoms in W\mathbf{W}:
    • Carbons: 6 (from diol)+4 (from two acetyl groups)=106 \text{ (from diol)} + 4 \text{ (from two acetyl groups)} = 10
    • Hydrogens: 1818
    • Oxygens: 44
  • Thus, the molecular formula of W\mathbf{W} is C10H18O4\mathrm{C}_{10}\mathrm{H}_{18}\mathrm{O}_4.
  • Option C is correct.

4. Oxidation of U\mathbf{U} to V\mathbf{V} and Option D

  • Oxidation of the primary diol U\mathbf{U} with Jones reagent (CrO3/H+\mathrm{CrO}_3 / \mathrm{H}^+) oxidizes both primary alcohol (−CH2OH-\mathrm{CH_2OH}) groups into carboxylic acid (−COOH-\mathrm{COOH}) groups: U→CrO3/H+V:HOOC−CH2−CH(CH3)−CH2−COOH\mathbf{U} \xrightarrow{\mathrm{CrO}_3/\mathrm{H}^+} \mathbf{V} : \mathrm{HOOC-CH_2-CH(CH_3)-CH_2-COOH}
  • Compound V\mathbf{V} is a dicarboxylic acid (3-methylpentanedioic acid).
  • Carboxylic acids react with aqueous sodium bicarbonate (NaHCO3\mathrm{NaHCO}_3) to liberate carbon dioxide (CO2\mathrm{CO}_2) gas, resulting in effervescence: R−COOH+NaHCO3→R−COONa+H2O+CO2↑\mathrm{R-COOH} + \mathrm{NaHCO}_3 \rightarrow \mathrm{R-COONa} + \mathrm{H}_2\mathrm{O} + \mathrm{CO}_2\uparrow
  • Option D is correct.

Conclusion

The correct options are A, C, and D.