1
$\begingroup$

Pyridinium chlorochromate (PCC) in $\ce{CH2Cl2}$ can be used to oxidise primary alcohols only to aldehydes. I can't however, find any reference of it oxidising methanol (which is strictly speaking not a primary alcohol). My question is, does PCC oxidise methanol to formaldehyde and if not, what can I use to achieve this reaction?

$\endgroup$
  • $\begingroup$ My textbooks don't spend much time on reactions with methyl derivatives and I'm struggling to find brief discussions of 'methyl chemistry' that isn't on a higher level. $\endgroup$ – Venter May 17 '18 at 19:21
  • $\begingroup$ www.chem.libretexts.org/Textbook_Maps/Organic_Chemistry_Textbook_Maps/Map%3A_Organic_Chemistry_(Smith)/Chapter_12%3A_Oxidation_and_Reduction/12.07_Oxidizing_Agents $\endgroup$ – tatan May 17 '18 at 19:49
  • 1
    $\begingroup$ Yes it can. Why would you want to do this? $\endgroup$ – Waylander May 17 '18 at 22:06
-2
$\begingroup$

Look at the examples given here:

enter image description here

(Ignore the stuff written with pen; I have a habit of taking notes when reading)

PCC is taking two hydrogen atoms – one from the carbon atom attached to the -OH group and the other one from the -OH group itself, and then making a C=O double bond. Methanol has both of these. So, PCC should be able to oxidise it to formaldehyde.

$\endgroup$

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.