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Aldehydes Ketones and Carboxylic Acids question

2007 · Shift 1 · Q12
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Aldehydes Ketones and Carboxylic Acids question

2007 · Shift 1 · Q12

JEE AdvancedChemistryAldehydes Ketones and Carboxylic AcidsMCQ+3 / −1
Statement 1 : p-Hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid. Statement 2 : o-Hydroxybenzoic acid has intramolecular hydrogen bonding.
  1. A
    Statement 1 is True, Statement 2 is True, Statement 2 is a CORRECT explanation for Statement 1
  2. B
    Statement 1 is True, Statement 2 is True, Statement 2 is NOT a CORRECT explanation for Statement 1
  3. C
    Statement 1 is True, Statement 2 is False
  4. D
    Statement 1 is False, Statement 2 is True
View written solutionFree

Correct answer: D

  1. Identify the compounds

    • ooo-Hydroxybenzoic acid = salicylic acid
    • ppp-Hydroxybenzoic acid = para-hydroxybenzoic acid
  2. Analyze Statement 2 first

    Statement 2 says: ooo-Hydroxybenzoic acid has intramolecular hydrogen bonding.

    This is true.

    In ooo-hydroxybenzoic acid, the −OH-OH−OH group and −COOH-COOH−COOH group are adjacent, so hydrogen bonding can occur within the same molecule:

    intramolecular H-bonding in o-hydroxybenzoic acid\text{intramolecular H-bonding in } o\text{-hydroxybenzoic acid}intramolecular H-bonding in o-hydroxybenzoic acid
  3. Effect of intramolecular vs intermolecular hydrogen bonding on boiling point

    • Intramolecular hydrogen bonding reduces association between molecules.
    • Intermolecular hydrogen bonding increases attraction between molecules, which tends to increase boiling point.

    Since ooo-hydroxybenzoic acid shows intramolecular H-bonding, its molecules are less associated with one another.

    On the other hand, ppp-hydroxybenzoic acid cannot form such intramolecular H-bonding due to the large separation of groups, so it forms stronger intermolecular hydrogen bonding.

    Therefore, ppp-hydroxybenzoic acid has higher boiling point than ooo-hydroxybenzoic acid.

  4. Analyze Statement 1

    Statement 1 says: ppp-Hydroxybenzoic acid has a lower boiling point than ooo-hydroxybenzoic acid.

    From the above reasoning, this is false.

    Actually,

    Boiling point of p-hydroxybenzoic acid>boiling point of o-hydroxybenzoic acid\text{Boiling point of } p\text{-hydroxybenzoic acid} > \text{boiling point of } o\text{-hydroxybenzoic acid}Boiling point of p-hydroxybenzoic acid>boiling point of o-hydroxybenzoic acid
  5. Evaluate the options

    • A: Statement 1 true, Statement 2 true, explanation correct ❌
    • B: Statement 1 true, Statement 2 true, explanation not correct ❌
    • C: Statement 1 true, Statement 2 false ❌
    • D: Statement 1 false, Statement 2 true ✅
  6. Final answer

    The correct option is:

    D\boxed{D}D​
  7. Comparison with stored correct answer

    Stored correct answer = D

    My derived answer = D

    So, the derived answer agrees with the stored correct answer.

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