Orgo Reactions

Reaction 1 (hydroboration oxidation)

Reagents: 1)BH3, THF / 2)H2O2, -OH

Anytime you have boron on top and peroxide at the bottom.

Add one alcohol antimark and it’s going to be syn addition.

Reaction 2 (Oxymercuration demercuration)

Reagents: 1) Hg(OAc)2, H2O(AREA OF FOCUS HERE) / 2) NaBH4

Area of Focus: Take H away from whatever is in that area, and you will add whatever is left following the rule of that reaction.

Adds an “O'” thing mark, anti-addition.

Reaction 3 Acid Catalyzed Reaction

Reagents: acid/base. Note: If they ever give you a generic acid/base and nothing else, you get to assume there is water in the solution.

Example: H2SO4

Area of Focus

Adds an “O” thing mark, but with possible rearrangements.

Reaction 4

Reagants: 1) what is important is OsO4 / 2) NaHSO3

Note: The moment you see an Os, you add two alcohols syn.

Reaction 5

Copycat Reagent: KMnO4, NaOH /(cold)

Add two alcohols syn.

Anything cold is below 25 degrees Celcius.

Reaction 6

McPBA

Forms an epoxide syn (intramolecular triangle)

McPBA can also be: RCO3H, Peroxy acid, or the figure like carboxylic acid but double OO at end.

Reaction 7

McPBA in acidic conditions

1) McPBA

2) You will have the generic acid, then like the area of focus

example:

1) McPBA

2) H+, H2O

You will add an alcohol from the McPBA antimark, add an “O” thing mark, and it is anti-addition overall.

Note: The oxygens can be labeled radioactively.

Reaction 8

McPBA in basic conditions

1) McPBA

2) You will be given a generic base, then the area of focus

example: 1)McPBA 2) NaOH, H20

Note: The oxygens can be labeled radioactively.

Reaction 9

Halogen with an “O” thing.

Halogens can be: Br, Cl, or I.

Adds one halogen antimark and one “O” thing mark and it is an anti-addition overall.

Reaction 10

Halogen with a solvent that does not have an “O” thing.

Common solvents: CCl4, CHCl3

Adds two halogens anti-addition.

HARD QUESTION KNOWLEDGE

If you ever have the “O” thing in the actual starting molecule, you will form an intramolecular reaction.

Reaction 11

With HBr, HC, HI.

Adds one halogen mark with possible rearrangements

Reaction 12

NOTE: ONLY BROMINE

1) HBR and ROOR at bottom

Adds one bromine antimark.

Reaction 13: (ENTER ALKYNE WORLD)

Similar to reaction 12

Example Reagents: HBR/ ROOR

You will have a 1mol/1eq, which is the first time doing the action, and may then have a 2mol/2eq, which would require doing the action again.

You break a pi bond and add one Br antimark.

Reaction 14

Similar to 11 (HBr, HCl, HI)

Never any rearrangements in triple bonds

Add one halogen mark.

Reaction 15

Similar to 10 - halogens

Adds 2 halogens antiaddition (trans).

Reaction 16

Similar to 9

Halogen with an “O” thing.

One halogen antimark, one “O” thing mark, anti addition overall.

If O thing is OH, that creates enol which undergoes tata.

Tata means that you erase pi bond, erase the hydrogen in the OH, and add double bond to O.

Reaction 17

Similar to 1

1) BH3, THF

2) H2O2, -OH

Add one alcohol antmark syn (cis) addition.

Here there is also enol and tata.