14
$\begingroup$

I'm tutoring few Class 12 students for their chemistry exams. I'm stuck with few problems. I don't know, if the key is wrong or I am wrong.

enter image description here

According to me product (A) must be the cyclic diene, as given in option (A). Now, I don't know, what happens when you heat cyclic diene with selenium. But I do know that, $\ce{SeO2}$ oxidizes allylic positions of alkenes into alcohols. But, none of the options given are fitting into that argument.

The answer given in the book is option (B). How can that be explained?

$\endgroup$
  • 1
    $\begingroup$ Some pre-aromatic hydrocarbons can be easily oxidized by sulfur or similar rather weak oxidants into aromatic hydrocarbons. It is different type of reactions and it is not general $\endgroup$ – permeakra Jan 15 '13 at 8:00
14
$\begingroup$

Assuming your Product A is correct then product B should be benzene. Selenium act as a mild oxidizing agent at temperature 220 °C to 330 °C. In the above reaction selenium oxidizes cyclohexadiene to form benzene.

Below is a reaction in which 1-methyl-1,3-cyclohexadiene is converted into toluene. enter image description here

you can also go to this link for more info

$\endgroup$
0
$\begingroup$

Since the treatment of your compound with sodium will result the formation of diene as both bromine elements have same affinity to remove otherwise as per wurtz reaction sodium generates alkyl compound . The diene here forms benzene as the se acts as the oxidizing agent As per the options available the answer is benzene

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

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