0
$\begingroup$

I have read there exist so called "magic" (super strong) acids which can provide a proton to saturated hydrocarbons, producing cation and hydrogen molecule. Can hydrides act in the same manner (pick a proton to form free hydrogen molecule)? And why?

Improve this question
$\endgroup$
1
  • $\begingroup$ Depends on hydride. $\endgroup$
    – Mithoron
    Dec 7 '18 at 20:19
0
$\begingroup$

The pKa of sodium or lithium hydride is (solvent dependent) about 35, the pKa of Butyl lithium is around 50 so clearly H- is not strong enough to tear a proton off an unactivated alkane pKa tables here

Improve this answer
$\endgroup$
5
  • 1
    $\begingroup$ Then again, cyclopentadiene is also a hydrocarbon, so... $\endgroup$
    – Ivan Neretin
    Dec 7 '18 at 19:43
  • 1
    $\begingroup$ Not exactly unactivated though as the cyclopentadienyl anion is aromatic $\endgroup$
    – Waylander
    Dec 7 '18 at 19:56
  • 1
    $\begingroup$ True, but there was no "unactivated" in the original question. $\endgroup$
    – Ivan Neretin
    Dec 7 '18 at 20:03
  • 1
    $\begingroup$ The OP asked about saturated hydrocarbons, which excludes cyclopentadiene, $\endgroup$
    – Waylander
    Dec 7 '18 at 20:45
  • $\begingroup$ OK, I stand corrected. $\endgroup$
    – Ivan Neretin
    Dec 7 '18 at 23:35

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.