Calculate number of isomers of C5H10, which does not decolorise cold alkaline KMnO4 solution.
Correct Answer :
Solution :
The correct answer is 7.
To find the number of isomers of C5H10 that do not decolorize cold alkaline KMnO4 solution, we can follow these step-by-step logical deductions:
1. Understanding the Reaction with Cold Alkaline KMnO4 (Baeyer's Reagent)
Cold alkaline KMnO4 solution is a well-known reagent used to test for unsaturation (carbon-carbon double or triple bonds).
Alkenes undergo syn-hydroxylation with this reagent, decolorizing the purple KMnO4 solution and forming a brown precipitate of MnO2.
Since the isomers of C5H10 do not decolorize this solution, they must not contain any carbon-carbon double bonds. Therefore, these isomers must be cyclic saturated hydrocarbons (cycloalkanes).
2. Calculating the Double Bond Equivalent (DBE)
For a molecular formula of CnH2n, the degree of unsaturation or Double Bond Equivalent (DBE) is calculated as:
Substituting C = 5 and H = 10 into the formula:
A DBE of 1 indicates the presence of either one double bond or one ring. Since double bonds are ruled out by the chemical test, all possible isomers must contain exactly one ring (cycloalkanes).
3. Systematically Listing all Cycloalkane Isomers of C5H10
We can categorize the isomers based on the ring size:
A. Five-Membered Ring:
1. Cyclopentane (1 isomer)
B. Four-Membered Ring:
2. Methylcyclobutane (1 isomer)
C. Three-Membered Ring:
3. Ethylcyclopropane (1 isomer)
4. 1,1-Dimethylcyclopropane (1 isomer)
5. 1,2-Dimethylcyclopropane: This compound contains two chiral carbon centers, giving rise to stereoisomers:
- cis-1,2-Dimethylcyclopropane: It has a plane of symmetry, making it an optically inactive meso compound. (1 isomer)
- trans-1,2-Dimethylcyclopropane: It lacks a plane of symmetry and exists as a pair of non-superimposable mirror images (enantiomers), namely the (1R, 2R) and (1S, 2S) configurations. (2 isomers)
4. Total Count of Isomers
Adding up all the counted structural and stereoisomers:
Total isomers = 1 (cyclopentane) + 1 (methylcyclobutane) + 1 (ethylcyclopropane) + 1 (1,1-dimethylcyclopropane) + 1 (cis-1,2-dimethylcyclopropane) + 2 (trans-1,2-dimethylcyclopropane)
Total = 7 isomers.
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