- A

- B

- C

- D

View written solutionFree
Correct answer: C
- Identify the first reaction: diazotization of aniline
Aniline in dilute HCl reacts with sodium nitrite at to form benzene diazonium chloride.
So the solution being added dropwise contains benzenediazonium chloride.
- Now identify the coupling components present in the second solution
The diazonium salt is added to an equimolar mixture of aniline and phenol in dilute HCl.
We must decide which aromatic ring will undergo azo coupling more readily.
- Effect of acidic medium on aniline and phenol
In dilute HCl:
-
Aniline gets protonated to form anilinium ion:
The group is strongly deactivating and meta-directing, so the ring becomes much less reactive toward azo coupling.
-
Phenol in acidic medium remains largely as phenol, being an activating group. Although less activated than phenoxide in basic medium, it is still much more reactive than protonated aniline.
Therefore, coupling occurs predominantly with phenol, not with aniline.
- Position of coupling in phenol
The group is ortho/para-directing.
During azo coupling of benzenediazonium chloride with phenol, substitution occurs mainly at the para position because:
- para position is activated,
- steric hindrance is lower than at ortho position.
Thus the major product is p-hydroxyazobenzene:
with at the para position relative to the azo linkage.
- Conclusion
So the major product is -hydroxyazobenzene (4-hydroxyazobenzene).
Hence the correct option is C.
- Comparison with stored correct answer
Stored correct answer = C
My derived answer = C
They agree.
More from Alcohols Phenols and Ethers
- The major product of the following reaction is : Includes diagram2019 · MCQ
- The major product of the following reaction is : Includes diagram2019 · MCQ
- The increasing order of the pKa values of the following compounds is : Includes diagram2019 · MCQ
- The major product 'X' formed in the following reaction is : Includes diagram2019 · MCQ
- The major product of the following reaction Includes diagram2019 · MCQ
- The major product of the following reaction is : Includes diagram2019 · MCQ
- The major product of the following reaction is Includes diagram2019 · MCQ
- Which of the following compounds reacts with ethylmagnesium bromide and also decolourizes bromine water solution:2019 · Multiple correct