- A

- B

- C

- D

View written solutionFree
Correct answer: C
-
Use the sodalime reaction first
Heating a carboxylic acid salt with sodalime causes decarboxylation:
Since [P] on heating with sodalime gives toluene , [P] must be a methyl benzoic acid (toluic acid), because removing from a methyl-substituted benzoic acid gives toluene.
So [P] is one of:
- -methyl benzoic acid (-toluic acid)
- -methyl benzoic acid (-toluic acid)
- -methyl benzoic acid (-toluic acid)
-
Now analyze bromination with in
This is electrophilic aromatic substitution.
In methyl benzoic acids, the substituents have directing effects:
- is ortho/para directing and activating.
- is meta directing and deactivating.
We need the compound that gives a single monobromo isomer.
-
Check each possible isomer
(i) -methyl benzoic acid: -methyl benzoic acid
Positions available for bromination are not all equivalent, so more than one product is possible. Hence, not suitable.
(ii) -methyl benzoic acid: -methyl benzoic acid
Again, the free positions are not symmetry equivalent, so bromination can give more than one isomer. Hence, not suitable.
(iii) -methyl benzoic acid: -methyl benzoic acid
Structure has para-substituted groups:
- at position 1
- 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:
- directs to 2, 6
- directs to 2, 6 (meta to )
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.
-
Verify molecular formula
-methyl benzoic acid has formula: Replacing one ring hydrogen by bromine gives: which matches the given product formula.
-
Conclusion
Hence [P] is -methyl benzoic acid (-toluic acid, 4-methyl benzoic acid).
Therefore, the correct option is C.
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