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An organic compound A has molecular form...

An organic compound A has molecular formula `C_7H_9N` and it forms a clear solution when dissolved in aqueous `KOH` solution of benzene sulphonyl chloride. A on treatment with `NaNO_2` and `HCl` at `0^@` C and then with 2-naphthol form an intensely coloured compound. Aslo A on treatment with `CH_3COCl` followed by electrophilic sustitution yields a single product. identify. A

A

4-emthylaniline

B

2-methylaniline

C

3-methylaniline

D

N-methylaniline

Text Solution

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The correct Answer is:
To solve the problem, we will follow a systematic approach based on the information provided in the question. ### Step 1: Analyze the Molecular Formula The organic compound A has the molecular formula \( C_7H_9N \). This indicates that it contains 7 carbon atoms, 9 hydrogen atoms, and 1 nitrogen atom. **Hint**: Look for structural features that can be derived from the molecular formula, such as the presence of functional groups. ### Step 2: Reaction with Benzene Sulphonyl Chloride The compound A forms a clear solution when dissolved in an aqueous KOH solution and treated with benzene sulphonyl chloride. This reaction is characteristic of primary amines, which react to form sulphonamides. **Hint**: Recall that primary amines will react with benzene sulphonyl chloride to form a clear solution, while secondary and tertiary amines will not. ### Step 3: Identify Possible Structures Given that A is a primary amine and has the formula \( C_7H_9N \), the possible structure could be an aromatic amine. The simplest aromatic amine with this formula is aniline (C6H5NH2). The presence of a methyl group suggests that we are dealing with a substituted aniline. **Hint**: Consider the position of the methyl group on the aromatic ring (ortho, meta, or para). ### Step 4: Reaction with NaNO2 and HCl When A is treated with NaNO2 and HCl at 0°C, it forms a diazonium salt. The subsequent reaction with 2-naphthol produces an intensely colored compound, which indicates the formation of a coupling product. **Hint**: The coupling reaction with 2-naphthol suggests that the amine is likely para-substituted, as this leads to stable colored products. ### Step 5: Electrophilic Substitution with CH3COCl The treatment of A with acetyl chloride (CH3COCl) followed by electrophilic substitution yields a single product. This indicates that the methyl group is likely in a position that allows for only one substitution product. **Hint**: The presence of the methyl group on the aromatic ring can influence the position of electrophilic substitution. ### Step 6: Determine the Structure of A Considering the above points, the most likely structure for A is 4-methyl aniline (p-toluidine), where the methyl group is in the para position relative to the amino group. **Hint**: Verify the structure by checking if it fits all the reactions described in the problem. ### Conclusion Based on the analysis, the organic compound A is identified as **4-methyl aniline** (p-toluidine). ### Summary of Steps 1. Analyze the molecular formula \( C_7H_9N \). 2. Recognize the reaction with benzene sulphonyl chloride indicates a primary amine. 3. Consider the structure of substituted aniline. 4. Understand the formation of a diazonium salt and its reaction with 2-naphthol. 5. Evaluate the electrophilic substitution with CH3COCl leading to a single product. 6. Conclude that A is 4-methyl aniline.

To solve the problem, we will follow a systematic approach based on the information provided in the question. ### Step 1: Analyze the Molecular Formula The organic compound A has the molecular formula \( C_7H_9N \). This indicates that it contains 7 carbon atoms, 9 hydrogen atoms, and 1 nitrogen atom. **Hint**: Look for structural features that can be derived from the molecular formula, such as the presence of functional groups. ### Step 2: Reaction with Benzene Sulphonyl Chloride ...
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A2Z-ORGANIC COMPOUNDS CONTAINING NITROGEN-Aromatic Amines And Diazonium Salts
  1. By reduction of mitrosobenzene which f the following is not obtained

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  2. Among the following compounds nitrobenzene, benzene, aniline and pheno...

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  3. An organic compound A has molecular formula C7H9N and it forms a clear...

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  4. Aniline on treatment with excess of bromine water gives

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  5. Which could not be directly prepared from 4-bromobenzenediazonium ion?

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  6. When an organic compound was treated with sodium nitrite and hydrochlo...

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  7. Derice a series of reaction of convert benzene into metachlorobromoben...

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  8. Aniline reacts with alkyl halide to give

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  9. Which of the following is regenerated at the end of the reaction?

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  10. Which of the following compounds does not react with NaNO2 and HCl?

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  11. An azo compoudn X is cleaved at the azo linkage by stannous chloride S...

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  12. Which one is less alkaline?

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  13. In the diazotasation of aniline with sodium nitrite and hydrochloric a...

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  14. Aniline and methyl amine can be differentiated by

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  15. Reaction of aniline with benzaldehyde is

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  16. In the reaction C6H5CHO+C6H5NH2rarrC6H5N=HCC6H5+H2O and compound C6H5N...

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  17. Electrophilic substitution of with bromine gives

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  18. p-chloro aniline and anilinium hydrochloride can be distinguished by

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  19. Identify the product Z in the following reacton C6H5NH2overset((AC)2O)...

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  20. Benzldehyde condenses with N, N-dimethylaniline in presence of anhydro...

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