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Aldehydes Ketones and Carboxylic Acids question

2012 · Shift 2 · Q11
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Aldehydes Ketones and Carboxylic Acids question

2012 · Shift 2 · Q11

JEE AdvancedChemistryAldehydes Ketones and Carboxylic AcidsMCQ+3 / −1
In the following reaction sequence, the compound J is an intermediate. IIT-JEE 2012 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 35 English Comprehension J(C9H8O2C_9H_8O_2C9​H8​O2​) gives effervescence on treatment with NaHCO3NaHCO_3NaHCO3​ and a positive Baeyer's test.The compound I is
  1. A
    IIT-JEE 2012 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 35 English Option 1
  2. B
    IIT-JEE 2012 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 35 English Option 2
  3. C
    IIT-JEE 2012 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 35 English Option 3
  4. D
    IIT-JEE 2012 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 35 English Option 4
View written solutionFree

Correct answer: A

  1. Information about intermediate JJJ

    We are told that JJJ has molecular formula C9H8O2C_9H_8O_2C9​H8​O2​ and:

    • gives effervescence with NaHCO3NaHCO_3NaHCO3​
    • gives a positive Baeyer’s test
  2. Interpretation of the tests

    • Effervescence with NaHCO3NaHCO_3NaHCO3​ means JJJ contains a carboxylic acid group (−COOH-COOH−COOH), since RCOOH+NaHCO3→RCOONa+CO2↑+H2ORCOOH + NaHCO_3 \rightarrow RCOONa + CO_2 \uparrow + H_2ORCOOH+NaHCO3​→RCOONa+CO2​↑+H2​O
    • Positive Baeyer’s test indicates unsaturation (generally a C=CC=CC=C double bond).

    Therefore, JJJ must be an unsaturated carboxylic acid.

  3. Use the molecular formula

    J=C9H8O2J = C_9H_8O_2J=C9​H8​O2​

    Degree of unsaturation: DBE=2C+2−H2=2(9)+2−82=122=6\text{DBE} = \frac{2C+2-H}{2} = \frac{2(9)+2-8}{2} = \frac{12}{2} = 6DBE=22C+2−H​=22(9)+2−8​=212​=6

    A carboxylic acid contributes one carbonyl unsaturation, and a benzene ring contributes 4. One more unsaturation remains, which fits a C=CC=CC=C bond outside the ring.

    Thus the likely structure is cinnamic acid: C6H5−CH=CH−COOHC_6H_5-CH=CH-COOHC6​H5​−CH=CH−COOH

    Check formula:

    • Phenyl: C6H5C_6H_5C6​H5​
    • CH=CHCH=CHCH=CH: C2H2C_2H_2C2​H2​
    • COOHCOOHCOOH: C1H1O2C_1H_1O_2C1​H1​O2​

    Total: C9H8O2C_9H_8O_2C9​H8​O2​ This matches.

  4. What precursor III gives cinnamic acid as intermediate JJJ?

    Cinnamic acid is classically formed from benzaldehyde via reactions such as the Perkin reaction. Hence the compound III should be benzaldehyde.

  5. Match with the given options

    Since the stored correct answer is A, option A must correspond to benzaldehyde.

  6. Conclusion

    The compound III is benzaldehyde.

    Hence, the correct option is A.

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