1
$\begingroup$

enter image description here

I do not understand how we obtain the product in option one. According to Free radical stability order tertiary carbon radical is more stable than secondary carbon radical which is more stable than primary carbon radical. So hydrogen selectivity should also follow the same order. Then why is it that we get option(1) instead of option (2). I’m only in high school so please try to keep it simple.

Improve this question
$\endgroup$

1 Answer 1

Reset to default
2
$\begingroup$

This question is based on relative rates of reaction of different $\ce{H}$ with halogens. In the free radical mechanism of chlorination of alkane, relative rate of reaction of $\ce{3^\circ : 2^\circ : 1^\circ}$ $\ce{H}$ is in order $5:3.8: 1$.

Using this, we get an idea about product amount. To get a rough estimate of relative amounts of different products, we multiply number of identical hydrogen and its rate of reaction with chlorine.

So there is only $1$ $3^\circ$ $\ce{H}$ and its rel. rate is $5$. So relative amount is $5$. For the $2^\circ$ $\ce{H}$, there are $2$ of them and their relative rate is $3.8$. So its relative amount is $2 \cdot 3.8 = 7.6$. Similar calculation for rest of the hydrogens will show you why given answer is correct.

Refer: Wikipedia

Improve this answer
$\endgroup$
8
  • $\begingroup$ Them number of primary hydrogens is 9. So the relative amount should be 9*1=9. Then percentage of primary chlorine should be (9/21.5)*100= 41%. Percentage of secondary chlorine should be (7.5/21.6)*100= 35%. Then shouldn’t primary monosubstitued chlorine be the major compound? $\endgroup$
    – Raheel
    Commented Jan 20, 2018 at 14:33
  • $\begingroup$ Raheeel No here s a catch. There are two types of one degree hydrogen present. $\endgroup$
    – King Tut
    Commented Jan 20, 2018 at 15:13
  • $\begingroup$ So I shouldn’t consider primary hydrogen on substituent carbon ie side chain. Am I right? $\endgroup$
    – Raheel
    Commented Jan 22, 2018 at 11:12
  • $\begingroup$ I am saying products 3 and 4 are not identical as hydrogen's replaced by chlorine in them are not identical $\endgroup$
    – King Tut
    Commented Jan 22, 2018 at 14:26
  • $\begingroup$ You take into account 3 and 4 as different product. Then find relative amount $\endgroup$
    – King Tut
    Commented Jan 22, 2018 at 14:28

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.