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An organic compound A has molecular form...

An organic compound A has molecular formula `C_(10)H_(17)Br` and it is non-resolvable. A does not decolourize brown colour of bromine water solution. A on treatement with `(CH_(3))_(2 COK//(CH_(3))_(3)COH` yields `B` as majot product. B on treatment with `H_(2)//Pt` yields `(C_(10)H_(16))` which on treatment with `CI_(2)//hv` yields three monochloro derivative. Also B on boiling with acidic permanganate solution yields `C(C_(10)H_(16)O_(3))C`. on heating with sodalime yields `D(C_(9)H_(16)O).D` on reducing with `LiAIH_(4)` followed yields `C(C_(10)H_(16)O_(3)).C` on heating with sodalime yields `D(C_(9)H_(16)O).D` on reducing with `LiAIH_(4)` followed by heating product with concentrated `H_(2)SO_(4)` yields `E(C_(9)H_(16))` as major product. E on treatment with ozone followed by work-up with `Zn-H_(2)O` yields 6-Ketononanal.
Compound A is:

A

B

C

D

none of these

Text Solution

AI Generated Solution

The correct Answer is:
To determine the structure of the organic compound A with the molecular formula C₁₀H₁₇Br, we will follow a systematic approach based on the information provided in the question. ### Step-by-Step Solution: 1. **Calculate the Degree of Unsaturation (DU)**: - The formula for calculating the degree of unsaturation is: \[ DU = \frac{2C + 2 - H - X}{2} \] where C is the number of carbon atoms, H is the number of hydrogen atoms, and X is the number of halogen atoms. - For compound A: - C = 10 - H = 17 - X (Br) = 1 - Plugging in the values: \[ DU = \frac{2(10) + 2 - 17 - 1}{2} = \frac{20 + 2 - 17 - 1}{2} = \frac{4}{2} = 2 \] - This indicates that there are 2 degrees of unsaturation, which could be due to either 2 rings, 2 double bonds, or 1 triple bond. 2. **Analyze the Reactivity with Bromine Water**: - The compound A does not decolorize bromine water, indicating that it does not contain any double bonds or triple bonds. Therefore, the degree of unsaturation must be attributed to rings. 3. **Determine the Structure of Compound A**: - Since A is non-resolvable (optically inactive), it must have a symmetrical structure. - Given that there are 2 degrees of unsaturation and the compound is non-resolvable, it is likely that A contains two identical rings that contribute to the non-optical activity. 4. **Propose a Possible Structure**: - A reasonable structure for compound A is 1,2-dibromo-1,2-dihydroxycyclohexane or a similar bicyclic compound that fits the criteria of having two rings and being non-resolvable. - The bromine atom can be attached to a carbon that is part of a symmetrical structure, ensuring that the compound remains optically inactive. 5. **Final Structure of Compound A**: - Based on the analysis, the structure of compound A can be represented as follows: - A is likely a bicyclic compound with two bromine atoms attached to the same carbon, making it achiral. ### Conclusion: The compound A is a bicyclic structure that is non-resolvable and does not react with bromine water. The exact structure can be confirmed through further analysis of the products formed in subsequent reactions.
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ALLEN-ALKYL AND ARYL HALIDE-EXERCISE
  1. Statement-I: Nucleophilic substitution reaction on an optically active...

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  2. Statement-I: Boiling point of alkyl halide increases with increases in...

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  3. An organic compound A has molecular formula C(10)H(17)Br and it is non...

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  4. An organic compound A has molecular formula C(10)H(17)Br and it is non...

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  5. An organic compound A has molecular formula C(10)H(17)Br and it is non...

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  6. An organic compound A has molecular formula C(10)H(17)Br and it is non...

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  7. Nucleophilic substitution reactions generally expressed as Nu^(-) +R...

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  8. Nucleophilic substitution reactions generally expressed as Nu^(-) +R...

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  9. Nucleophilic substitution reactions generally expressed as Nu^(-) +R...

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  10. Nucleophilic substitution reactions generally expressed as Nu^(-) +R...

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  11. Nucleophilic aliphatic substitution reaction is mainly of two types: S...

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  12. Nucleophilic aliphatic substitution reaction is mainly of two types: S...

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  13. Nucleophilic aliphatic substitution reaction is mainly of two types: S...

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  14. An optically active compound A (assume dextrorotatory) has the molecul...

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  15. An optically active compound A (assume dextrorotatory) has the molecul...

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  16. Select the member of each pair that shows rate of S(N)2 reaction with ...

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  17. Of the following statements which are true for S(N)1 reaction. (a) T...

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  18. Of the following statements , which are true for S(N)2 reaction. (a)...

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  19. Arrange the isomers of molecular formula C(4)H(9)CI in order of decrea...

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  20. There is an overall 29-fold difference in reactivity of 1-chlorohexane...

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