Stereochemistry of the following

[rippinitez]

Does anyone know how to figure out the stereochemistry of this molecule? If you can please explain how you came up with answer. I have the answer but don't understand how the book came up with it. I'll share after a few posts.

This will prevent ppl. from trying to justify the answer.

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[Ibraiz]

Does anyone know how to figure out the stereochemistry of this molecule? If you can please explain how you came up with answer. I have the answer but don't understand how the book came up with it. I'll share after a few posts.

This will prevent ppl. from trying to justify the answer.

Is the top one 'R' and bottom one 'S'?

 

[299678]

R for top S for bottom?

 

[deleted323428]

Top is S bottom is R

 

[rippinitez]

I also thought this is a molecule with 2 chiral carbons, top R and bottom S.

But the answer actually doesn't give the R or S orientation but simply states that it's a meso compound. I don't see how it can be a meso compound since there doesn't appear to be a line of symmetry.

 

[RSD2014]

Does anyone know how to figure out the stereochemistry of this molecule? If you can please explain how you came up with answer. I have the answer but don't understand how the book came up with it. I'll share after a few posts.

This will prevent ppl. from trying to justify the answer.

Top R
Bottom S

Meso, Maybe 180 degree rotation on Carbon#2?

 

[rippinitez]

So when and where are you supposed to do a 180 flip to check for meso compounds?

 

[RSD2014]

So when and where are you supposed to do a 180 flip to check for meso compounds?

It's a single bond between Carbon#1 and Carbon#2, there is always free rotation. Check for meso especially when you have similar substituent groups on both carbons. Substituents connected to Carbon#2 can rotate 180 degree.

 

[Baylor2011]

It's a single bond between Carbon#1 and Carbon#2, there is always free rotation. Check for meso especially when you have similar substituent groups on both carbons. Substituents connected to Carbon#2 can rotate 180 degree.

Couldn't have said it better myself

 

[rippinitez]

Ok that makes sense. Just to make sure, the substituents on carbon 1 can also rotate 180 degrees right?

 

[Baylor2011]

That's correct. Anytime there's a Carbon-Carbon single bond, there is free rotation about that bond. Now...It's easier to see it if you draw it in 3D...make sure when you rotate it you keep the substituents in the right order.

 

[rippinitez]

Thanks my man

 

[Frederico Albin]

Finally I see another brazilian in this forum

 

[rippinitez]

For sure. Rare breed in the states.