Question

Can Anyone tell me is this molecule is a meso compound? Thanks!!!!

Answer 1

@Kainui

Answer 2

What do you think? Is it a meso compound?

Answer 3

no.4

Answer 4

sorry about the quality

Answer 5

Ahh, that's no problem I can see it just fine. First off, what do you think it is? What does it mean for a molecule to be meso?

Answer 6

and must have at least 2 chiral centres

Answer 7

and can be folded each half if it on the other half perfectly

Answer 8

my professor told me that's a meso compound but it can't be, can it?

Answer 9

Am I right?

Answer 10

Well your professor told you it was meso because it is indeed meso, but I see how it is confusing! I suggest you draw out the structure and label all the chiral centers with a *

Answer 11

Really?is it?

Answer 12

but it cannot be folded, now I'm so confused, there r 3 chiral centres

Answer 13

only 2 sorry

Answer 14

2 chiral cntres

Answer 15

Good catch! I think I see what your confusion is, what do you mean when you say "folded"?

Answer 16

that if I ostensibly took each half of a meso compound, I could fold one half on the other

Answer 17

How do you know it's a meso compund?

Answer 18

Do you maybe have a model kit lying around? Try to draw the bond line structures of all the different stereochemistry, and we can talk about why it is if you don't figure it out in the process of drawing them. =)

Answer 19

Think about that middle carbon that I'm assuming you accidentally thought was a chiral center a moment ago, maybe that will help?

Answer 20

but if there were only 2 carbons, it would still be a meso compound right?

Answer 21

If so, I think I got it

Answer 22

I mean, if the a-chiral centre were there, and only 2 chiral carbons would remainm would it still be a meso?

Answer 23

Yeah, as long as you add/remove all the other substituents in a symmetrical way it will stay meso. I like to think of meso as meaning you can rotate it upside down and get the same thing or you can reflect it through the plane to get the same thing.

So instead of this molecule having 4 different isomers like we might expect, 2 of them are really just the same thing but drawn "forward" and "backwards" so we really have 3 isomers here.

Answer 24

I fixed the first sentence there to say "stay meso" instead of "stay the same" lol

Answer 25

lol you're brilliant! Thanks allot!

Answer 26

I think now I get it

Answer 27

it makes much more sense to me now

Answer 28

Haha I think you're pretty smart yourself, you are really quick and corrected yourself before I could, you could be really good at organic chemistry some day I think!

Answer 29

I hope so! Thanks!!!! Have an awesome day!

Answer 30

Yeah any time you need help in chemistry, tag me, I appreciate good questions by good people!

Answer 31

I shall! You've brought me so much confidence now, truly made my day!