Stereochem in organic chem?

[LoLCareerGoals]

Are you guys memorizing all the stereochemical details of organic reactions? Been looking through all the alkene reactions and # of different permutations is getting pretty large, just curious if I might be overdoing it memorizing all this ish.

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[dontbeanegaton]

It's probably not worth a whole lot of points to go through memorizing all the catalysts. I don't think it's a probable discrete question, and if stereochemistry comes up in passage, it's usually hinted at in mechanism drawings or the passage.
Then again, I need more O chem review myself.

 

[orgohacks]

Are you guys memorizing all the stereochemical details of organic reactions? Been looking through all the alkene reactions and # of different permutations is getting pretty large, just curious if I might be overdoing it memorizing all this ish.

There's really only 3 permutations:

1) all the reactions that go through carbocations (HCl, HBr, HI, H3O(+)) follow Markovnikoff's rule and have random stereochemistry.
2) all the reactions that go through 3-membered rings (Br2, Cl2, I2, Hg(OAc)2/H2O, etc) also follow Markovnikoff's rule (in cases where 2 different groups add) and have "anti" stereochemistry.
3) all the reactions that are "concerted" (epoxidation, hydrogenation, hydroboration, dihydroxylation) have "syn" stereochemistry, and hydroboration is anti-Markovnikoff.

This helps to simplify things into 3 buckets instead of about 15

[One exception is radical addition of HBr, which is anti-Markovnikoff and has random stereochemistry]

 

[Narmerguy]

There's really only 3 permutations:

1) all the reactions that go through carbocations (HCl, HBr, HI, H3O(+)) follow Markovnikoff's rule and have random stereochemistry.
2) all the reactions that go through 3-membered rings (Br2, Cl2, I2, Hg(OAc)2/H2O, etc) also follow Markovnikoff's rule (in cases where 2 different groups add) and have "anti" stereochemistry.
3) all the reactions that are "concerted" (epoxidation, hydrogenation, hydroboration, dihydroxylation) have "syn" stereochemistry, and hydroboration is anti-Markovnikoff.

This helps to simplify things into 3 buckets instead of about 15

[One exception is radical addition of HBr, which is anti-Markovnikoff and has random stereochemistry]

If only it was taught this way all the time Great post.

 

[circulus vitios]

If only it was taught this way all the time Great post.

He should definitely write his own textbook.