Question

Identify all the possible monochloro structural isomers expected to be formed on free radical monochlorination of ${\left({CH}_3\right)}_2{CHCH}_2{CH}_3$.
In the given molecule, there are four different types of hydrogen atoms. Replacement of these hydrogen atoms will give the following?

• A. ${\left({CH}_3\right)}_2{CHCH}_2{CH}_{2}Cl$
• B. ${\left({CH}_3\right)}_{2}CHCH\left(Cl\right){CH}_3$
• C. ${\left({CH}_3\right)}_{2}C\left(Cl\right){CH}_2{CH}_3$
• D. ${CH}_{3}CH\left({CH}_{2}Cl\right){CH}_2{CH}_3$

Answer 1

The correct option is C ${\left({CH}_3\right)}_{2}C\left(Cl\right){CH}_2{CH}_3$

Given compound is ${\left({CH}_3\right)}_{2}CH{CH}_2{CH}_3$.

From the knowledge of stability of free radicals $3^0>2^0>1^0$.

So, the possible free radical generation is at $3^0$ carbon.

$\Rightarrow$ So, the possible product formation after free radical addition of one chlorine is.

Option - C.