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Basics of Organic Chemistry question

2011 · Shift 0 · Q4
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Basics of Organic Chemistry question

2011 · Shift 0 · Q4

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Identify the compound that exhibits tautomerism.
  1. A
    Lactic acid
  2. B
    2-Pentanone
  3. C
    Pheno
  4. D
    2- Butene
View written solutionFree

Correct answer: B

  1. Recall the condition for tautomerism

    Tautomerism, especially keto-enol tautomerism, is shown by compounds having:

    • a carbonyl group (\ceC=O)\left(\ce{C=O}\right)(\ceC=O), and
    • at least one α\alphaα-hydrogen on the carbon adjacent to the carbonyl carbon.

    Then the equilibrium is: \ceR−CO−CH2−R′<=>R−C(OH)=CH−R′\ce{R-CO-CH2-R' <=> R-C(OH)=CH-R'}\ceR−CO−CH2−R′<=>R−C(OH)=CH−R′

  2. Check each option

    A: Lactic acid

    Lactic acid is \ceCH3−CH(OH)−COOH\ce{CH3-CH(OH)-COOH}\ceCH3−CH(OH)−COOH. It contains a carboxylic acid group, not a simple aldehyde/ketone system suitable for normal keto-enol tautomerism in this context. Hence, it is not typically considered to exhibit tautomerism here.

    B: 2-Pentanone

    Structure: \ceCH3−CO−CH2−CH2−CH3\ce{CH3-CO-CH2-CH2-CH3}\ceCH3−CO−CH2−CH2−CH3 It is a ketone and has α\alphaα-hydrogens on both sides of the carbonyl group. Therefore, it shows keto-enol tautomerism.

    Example: \ceCH3−CO−CH2−CH2−CH3<=>CH3−C(OH)=CH−CH2−CH3\ce{CH3-CO-CH2-CH2-CH3 <=> CH3-C(OH)=CH-CH2-CH3}\ceCH3−CO−CH2−CH2−CH3<=>CH3−C(OH)=CH−CH2−CH3 So, this compound exhibits tautomerism.

    C: Phenol

    Phenol mainly exists as \ceC6H5OH\ce{C6H5OH}\ceC6H5OH. Although special valence tautomeric forms may be discussed in advanced contexts, it is not the standard answer for simple tautomerism questions of this type. So, not correct here.

    D: 2-Butene

    Structure: \ceCH3−CH=CH−CH3\ce{CH3-CH=CH-CH3}\ceCH3−CH=CH−CH3 This is an alkene and does not have the required carbonyl-α\alphaα-hydrogen arrangement. Hence, it does not show keto-enol tautomerism.

  3. Conclusion

    The compound that exhibits tautomerism is: 2-Pentanone\boxed{\text{2-Pentanone}}2-Pentanone​

  4. Comparison with stored correct answer

    Stored correct answer: B

    Derived answer: B

    These match.

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