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Aldehydes Ketones and Carboxylic Acids question

2020 · 4 Sep · Shift 1 · Q5
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  5. /2020 · 4 Sep · Shift 1 · Q5

Aldehydes Ketones and Carboxylic Acids question

2020 · 4 Sep · Shift 1 · Q5

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
[P] on treatment with Br2Br_2Br2​/FeBr3FeBr_3FeBr3​ in CCl4CCl_4CCl4​ produced a single isomer C8H7O2BrC_8H_7O_2BrC8​H7​O2​Br while heating [P] with sodalime gave toluene. The compound [P] is
  1. A
    JEE Main 2020 (Online) 4th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 168 English Option 1
  2. B
    JEE Main 2020 (Online) 4th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 168 English Option 2
  3. C
    JEE Main 2020 (Online) 4th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 168 English Option 3
  4. D
    JEE Main 2020 (Online) 4th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 168 English Option 4
View written solutionFree

Correct answer: C

  1. Use the sodalime reaction first

    Heating a carboxylic acid salt with sodalime causes decarboxylation: RCOONa→ΔsodalimeRHRCOONa \xrightarrow[\Delta]{\text{sodalime}} RHRCOONasodalimeΔ​RH

    Since [P] on heating with sodalime gives toluene (C6H5CH3)(C_6H_5CH_3)(C6​H5​CH3​), [P] must be a methyl benzoic acid (toluic acid), because removing −COOH-COOH−COOH from a methyl-substituted benzoic acid gives toluene.

    So [P] is one of:

    • ooo-methyl benzoic acid (ooo-toluic acid)
    • mmm-methyl benzoic acid (mmm-toluic acid)
    • ppp-methyl benzoic acid (ppp-toluic acid)
  2. Now analyze bromination with Br2/FeBr3Br_2/FeBr_3Br2​/FeBr3​ in CCl4CCl_4CCl4​

    This is electrophilic aromatic substitution.

    In methyl benzoic acids, the substituents have directing effects:

    • −CH3-CH_3−CH3​ is ortho/para directing and activating.
    • −COOH-COOH−COOH is meta directing and deactivating.

    We need the compound that gives a single monobromo isomer.

  3. Check each possible isomer

    (i) ooo-methyl benzoic acid: 222-methyl benzoic acid

    Positions available for bromination are not all equivalent, so more than one product is possible. Hence, not suitable.

    (ii) mmm-methyl benzoic acid: 333-methyl benzoic acid

    Again, the free positions are not symmetry equivalent, so bromination can give more than one isomer. Hence, not suitable.

    (iii) ppp-methyl benzoic acid: 444-methyl benzoic acid

    Structure has para-substituted groups:

    • −CH3-CH_3−CH3​ at position 1
    • −COOH-COOH−COOH at position 4

    The unsubstituted positions are 2, 3, 5, 6. By symmetry:

    • positions 2 and 6 are equivalent
    • positions 3 and 5 are equivalent

    Now directing effects:

    • −CH3-CH_3−CH3​ directs to 2, 6
    • −COOH-COOH−COOH directs to 2, 6 (meta to −COOH-COOH−COOH)

    So both groups direct bromination to the same positions (2 and 6), and these two are equivalent by symmetry.

    Therefore, only one monobromo product is formed.

  4. Verify molecular formula

    ppp-methyl benzoic acid has formula: C8H8O2C_8H_8O_2C8​H8​O2​ Replacing one ring hydrogen by bromine gives: C8H7O2BrC_8H_7O_2BrC8​H7​O2​Br which matches the given product formula.

  5. Conclusion

    Hence [P] is ppp-methyl benzoic acid (ppp-toluic acid, 4-methyl benzoic acid).

    Therefore, the correct option is C.

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