How many different monochlorination products would be obtained on free radical chlorination of methyl cyclobutane?Correct answer is '8'. Can you explain this answer?

Question

Answer

After free radical halogenation of methyl cyclobutane, we have its 8different isomers. They are as follow:-

From i) and ii), we get only positional isomers. From iii) we will have 2 isomers, cis and Trans. They won't show a chiral centre.
In iv) we have 2 chiral centres which will give us 4 isomers.So, in total there would be 4+2+1+1 = 8 isomers.

Answer

(Chloromethl)cyclobutane, 1-Chloro -1-methylcyllobutane, 1-Chloro-2-methylcyclobutane and 1-Chloro-3-methylcyclobutane are structural isomers. 1-Chloro-2-methylcyclobytane have 2 geometrical isomers. Each geometrical isomers have enantiomer. Hence it have 4 isomers. 1-Chloro-3-methylcyclobutane have geometrical isomers cis and trans. Hence it have 2 isomers. (Chloromethyl)cyclobutane =11-Chloro 1-methylcyclobutane =11-Chloro-2-methylcyclobutane=41-Chloro-3-methylcyclobutane=2Total 8 isomers.

Answer

The monochlorination of methyl cyclobutane results in the formation of 8 different products.

Methyl cyclobutane is a cyclic compound consisting of a cyclobutane ring with a methyl group attached to it. When this compound undergoes free radical chlorination, chlorine atoms can replace one of the hydrogen atoms in the molecule, leading to the formation of different monochlorination products.

Formation of different monochlorination products:

1. Primary carbon: The chlorine atom can substitute one of the hydrogen atoms present on the primary carbon atom of the cyclobutane ring. There are two primary carbon atoms in methyl cyclobutane, so two different products can be formed.

2. Secondary carbon: The chlorine atom can substitute one of the hydrogen atoms present on the secondary carbon atoms of the cyclobutane ring. There are two secondary carbon atoms in methyl cyclobutane, so two different products can be formed.

3. Tertiary carbon: The chlorine atom can substitute one of the hydrogen atoms present on the tertiary carbon atom of the cyclobutane ring. There is only one tertiary carbon atom in methyl cyclobutane, so only one product can be formed.

4. Bridgehead carbon: The chlorine atom can substitute one of the hydrogen atoms present on the bridgehead carbon atom of the cyclobutane ring. There is only one bridgehead carbon atom in methyl cyclobutane, so only one product can be formed.

Total number of products:

To calculate the total number of products, we add up the number of products from each category:

Primary carbon: 2 products
Secondary carbon: 2 products
Tertiary carbon: 1 product
Bridgehead carbon: 1 product

2 + 2 + 1 + 1 = 6

However, there is an additional factor to consider. Methyl cyclobutane exists in two different conformations: the chair and boat conformations. When chlorination occurs, both conformations can lead to different products. Since each conformation can give rise to the same set of products, we need to multiply the total number of products by 2.

6 x 2 = 12

However, some of the products obtained are the same, but in different orientations. These are called enantiomers. Since we are only interested in counting distinct products, we divide the total by 2.

12 ÷ 2 = 6

Therefore, the correct answer is 6 distinct monochlorination products.

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