[plexx92]

Say you had a secondary alcohol and you wanted to replace the hydroxyl group with a carbon and then attach another hydroxyl group to said carbon. This is a discussion about how one might go about doing that. Different strategies and approaches.

[Honclbrif]

Go from something like 2-propanol to 2-methyl-1-propanol? It can be done, but not easily in one step.

[plexx92]

Yes, that is the process.

[Honclbrif]

You'd have to add a carbon. What are some good C1 nucleophiles, and how would you make the alcohol an electrophile?

[qbkr21]

here is one such way.  there are however a host of others.

Say you had a secondary alcohol and you wanted to replace the hydroxyl group with a carbon and then attach another hydroxyl group to said carbon. This is a discussion about how one might go about doing that. Different strategies and approaches.

[Honclbrif]

So how would you go about forming that ylid?

[qbkr21]

by combining triphenylphosphine with iodomethanol

So how would you go about forming that ylid?

[discodermolide]

It is the enolate of an aldehyde the equilibrium will be completely to the aldehyde side.

[Dan]

So how would you go about forming that ylid?

by combining triphenylphosphine with iodomethanol

Iodomethanol does not exist exist (in a practical sense). It would decompose to formaldehyde and HI.

[Honclbrif]

"by combining triphenylphosphine with iodomethanol"

Are you trolling?

[orgopete]

@plexx92
I missed that class. Were you discussing Grignard reagents?