Weird Reagents-- Orgo II Exam II

PPh3 main purpose

Strong Base

If I see PPh3 as the only reagent, what happens?

It acts as a nucleophile, and it wants to go on a carbon and kick a double bond off of a C=O (or it wants to remove an -X)

Why is there a PPh3 with my Pd?

It won’t react, it’s just there to stabilize Pd

Why is there a Zn(Hg) + HCl?

It will remove a =O and replace it with two hydrogens (reduction)

Why is there an NH2NH2 and -OH?

It will reduce a =O into 2 C-H bonds (reduction)

Why is there a R2CuLi in my reagents?

So you can add one of the R groups to wherever the -X is on your starting product (and there won’t be a change in geometry)

Why is there Pd and a strong base (like Et3N) in my reaction? PPh3 can also be there at times

Adds the C=C bond on the second starting product to wherever the -X currently is on the first starting product. Also it will be trans.

What is Pd(OAc)2?

A cheap source of Pd: act like (OAc)2 doesn’t exist

Why is there a Pd, a base, and a starting product with a B(OH)2 on it?

Because you are going to add the R connected to B(OH)2 to the place where the -X is in the other starting product, and it will retain alkene geometry

If I see Pd, PPh3 and a RB(OH)2 in a reaction, what is it?

Suzuki: add R to -X’s current spot

What does KMnO4 do? 

Turns -CH3 into -COOH

I see the word “Swern”. What is going to happen?

A primary or secondary alcohol is going to become an aldehyde substituent (formyl group) or a ketone substituent (acetyl group)

I see the word “TEMPO” and I am scared.

A primary (or sometimes secondary) alcohol is going to become an aldehyde substituent (formyl group)

I see the word “PCC” and I am scared.

A primary (or sometimes secondary) alcohol is going to become an aldehyde substituent (formyl group)

I have DMSO, (COCl)2, followed by a strong base

Baby girl that is another way to say Swern reaction! Turn alcohol into aldehyde or ketone.

I see NaOCl and HOAc

Make the secondary alcohol a ketone.

I see O3 with like a ton of stuff after it

Your C=C double bond is going to become two C=O bonds, cleaving the molecule.

I see H2SO4, Hg, and H20

Your alkyne is now a ketone (acetyl) on the more substituted carbon

I see Sia2BH

Your alkyne is now an aldehyde (formyl) on the less substituted carbon

I see LiALH4 and other stuff and a temperature

Your Acyl Chloride is now an Aldehyde

I see LiAlH4 with nothing else

Your carboxylic acid or aldehyde is now a primary alcohol.

I see DIBAL-H, hexane, and H2O

Your Ester or Nitrile is now an aldehyde

I see (i-Bu)2AlH

That is DIBAL queen

What dies Grignard reagent do to a nitrile?

CN turns into COR

What does RLi, Et2O, and H3O do to a nitrile?

Turns CN into COR

What is TsOH :)

A proton donor 

What is Ph3P-R?

Wittig reagent, reacts with aldehyde/ketone to turn =O into =R