Question

Cyclic compound A has molecular formula C5H10 and undergoes monochlorination to yield exactly three different constitutional isomers. Identify compound A and show the monochlorination products.

Answer 1

Answer:

A: 1,2-dimethylcyclopropane

Explanation:

The possible cyclic structure with formula C₅H₁₀ are shown in the image.

A is a cyclic compound. On monochlorination, A yields 3 products.

To have 3 products on monochlorination, there should be three different carbon atoms.

Considering structure 1, all carbons have same nature, thus only one product will be formed and thus not a structure of A.

Considering structure 2, there are two different carbon atoms, thus two different structure are formed and thus not a structure of A.

Considering structures 3 and 4 , there are four different carbon atoms, thus four products will be formed and either of them are not a structure of A.

Considering structure 5, there are three different carbon atoms,  thus three different structure are formed and thus the A is structure 5.

Answer 2

The monochlorination products are 1,2-dimethylcyclopropane, 1,3-dichlorocyclopentane, and  1,1-dichlorocyclopentane.

What is Monochlorination?

Monochlorination is the process in which substitution of one atom with chlorine atoms occur.

Given,

When $C_5H_1_0$ undergoes chlorination, it yields three different constitutional isomers.

So, the possible molecules are pentene and cyclopentane.

By monochlorination we get only one product that is 1-chlorocyclepentane.

By dichlorination of the compound, we get three products that are 1,2 -dichlorocyclopentane, 1,3-dichlorocyclopentane, and  1,1-dichlorocyclopentane respectively as given in the diagram.

Thus, the products are 1,2 -dichlorocyclopentane, 1,3-dichlorocyclopentane, and  1,1-dichlorocyclopentane.

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