Alkyne Reactions (Live Recording) Organic Chemistry Practice Session

[@Leah4sci]

Alkyne Practice Workshop + Live Session Notes a Leah4sci.com/orgolive (along with a heads up for additional upcoming exam review sessions) on my website: Leah4sci.com/orgolive

[@iremsoylu7917]

at 41:09, could it be dissolving metal reduction? since we have both Na+ and NH3

[@Leah4sci]

Dissolving metal reduction requires a neutral radical sodium rather than Na+ which we have here. Na+ is a non-reactive spectator ion

[@iremsoylu7917]

oh okay, thank you so much@@Leah4sci

[@goddaniel9478]

At 48:15 what other reagents could we use with H2 to create the same product? Really would love to know. My final is tomorrow and your videos are great! First time Orgo but I’m going to pass

[@Leah4sci]

Another option here is alkyne hydroboration to an aldehyde followed by reduction to the primary alcohol

[@alejandrosantoyo3905]

@22:38 is it possible to treat the alkyne w/ 1eq HCL then 1eq HCL/ROOR? for the same product? or 1.H2/Pd and then Cl2?

[@Leah4sci]

You wouldn't be able to isolate the alkene product. I think I covered this at some point later in the lecture about why you can't use just 1 equivalent to isolate the alkene product

[@sahanakumar3614]

For the retrosynthesis at 24 minutes, could you do the first step as HCl and then do the second step with HCl in peroxide to get anti-markovnikov addition? Thank you for your videos!

[@Leah4sci]

As I show later in the video, 1M HCl won't stop at a monochlorinated alkene

[@aa-fp4wn]

what are the odds, was just studying your alkyne sheet for an exam i have on sunday

[@Leah4sci]

Perfect timing!! Let me know how you feel about sunday's exam after completing this video and the associated worksheet

[@tylerturner506]

Hey Leah! For the problem around 48 minutes why does it seem as though the OH group added cis to the molecule.

[@Leah4sci]

That is simply how I chose to draw it. There are no stereocenters in this molecule. Therefore, we don't have to worry about stereochemistry. Remember that cis and trans are used to refer to the orientation of groups around a double bond (which we don't have here) or to the orientation of groups on either side of the face of a ring (which we also don't have here). This molecule is purely made of single bonds, around which we have free rotation. Meaning, such a structure is not so rigid as one with a pi bond.

[@alejandrosantoyo3905]

could you have used H2 and Pd to reduce the alkyne to an alkene @48 ?

[@alejandrosantoyo3905]

nvm that would cause a full reduction to an alkane, thanks sm!

[@Leah4sci]

glad you're all set

[@smugcat723]

Do you know what would help the best when studying for the ACS Organic Chemistry exam?

[@Leah4sci]

Yes! I wrote an entire guide on it here: leah4sci.com/acs

[@Leya13_5]

Leah I love you

[@Leah4sci]

Aww thanks!

[@Leya13_5]

@@Leah4sci I got an A