Which of the following compounds are chiral? Draw each compoun...

Question

Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.
(e) (R,R)-2,3-dibromobutane
(f)

(e) (R,R)-2,3-dibromobutane

(f) e,f

Accepted Answer

All right. Hello everyone. So this question is asking us to consider the following compounds. For part one, we have RR 23 Di Chloro Butane and for part two, we have two R three s 23 Diamo three hydroxy Pentel excuse me, propel using fissure projections, draw each compound in its most symmetric confirmation, draw any mirror plane, install any asymmetric carbon indicate if the compound is Cairo and label any mesal compounds. All right. So recall first and foremost that a plane of symmetry is an imaginary plane that is bisecting an object into two halves that are identical to each other. Now, meso compounds are compounds that are actually a chiral despite having chiral centers within them. This is because meso compounds are compounds that are superimposable mirror images of each other. Now, a chiral center can also be referred to as an asymmetric carbon or an asymmetric center. And those are atoms more specifically carbon atoms that are bound to four different substituents or four different atoms. So with this in mind, let's start by drawing out the Fisher projection of RR 23 Di Chloro Butane. So first, I'm going to start here by drawing out the four carbon chain. OK. So from here, recall that R or S configuration can be determined using the position of the lowest priority group. Our chiral centers happen to be positions two and three on the parent chain. And of the four substituents connecting to each chiral center hydrogen would be the lowest priority because it would have the smallest atomic number. So here, chlorine by contrast would have first priority because chlorine would have the largest atomic number. So from here, we can showcase or or s configuration by tracing a path from the first to the fourth priority and seeing in which direction it goes. For example, right now I placed on carbon two here, I've placed chlorine on the left side and hydrogen on the right side, chlorine having the largest atomic number would have first priority and hydrogen would have fourth or last priority. Now, in between the methyl carbon and carbon number three of the parent chain, carbon three of the parent chain would have second highest priority because it is attached two atoms that have higher atomic numbers. On the other hand, rch three is simply a methyl group that is connecting only to hydrogens that have smaller atomic numbers though, because of that point of difference, our methyl group, our methyl carbon is going to have third highest priority. So in this particular case, we call it in fisher projections. The horizontal lines represent those that are pointing towards you So this means that hydrogen, our fourth priority, our lowest priority is actually in the front. So one tracing a path from the first to the highest refers to the lowest priorities. If the lowest priority group is pointing in the fund and this path is going in a counterclockwise direction, then that is going to confirm that this is the R configuration. So that confirms that chlorine is chlorine and hydrogen are in the right spot. And we can do the same thing when comparing the priority order of carbon number three of the parent chain as well. So once again, the hydrogen is going to be pointing in the front. So when drawing a path from the first to the lowest priority, once again, we do so in a counterclockwise direction. So when the lowest priority group is in front and the path is going counterclockwise, that is also our configuration. So here to correctly show our stereo chemistry in the fisher projection on carbon number two, chlorine should be pointing to the left and on carbon number three, chlorine should be pointing to the right. And once again, carbons two and three are the chiral centers because they both have four different substituents connecting to them. So I'm going to start both of these. So now the question is if the compound is Cairo or if its a meso compound to understand the answer to this question, we're going to go ahead and draw the mirror image of the fisher projection we just drew. So here I'm drawing out the same carbon chain except I'm swapping the horizontal substituents here based on the mirror image, we can see that they are non superimposable. So this is not a meso compound rather, both of these are anant omer of each other, which means that part one, our molecule is chiral. So now let's move on to part two. Now for part two, I'm going to go ahead and simply redraw the Fisher projection that we are provided here. So that's an aldehyde on the top. On carbon number two, the amino group is on the right. And on carbon number three, the amino group is on the left. So here we can see that carbons two and three each have four different substituents, which means that both of these are asymmetric carbon. So now to understand if it's a meso compound or not, let's go ahead and draw out its mirror image. So when drawing the mirror image and swapping the horizontal substituents, we can see that these mirror images are non superimposable once more. So if it has a non superimposable mirror image, it has an inane tum mirror, which means that it is Cairo and not a meso compound and there you have it. So here are the answers to parts one and two. And so with that being said, thank you so very much for watching. And I hope you found the softball

Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.
(e) (R,R)-2,3-dibromobutane
(f)

Key Concepts

Chirality

Asymmetric Carbon Atoms

Meso Compounds

Watch next

Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.(e) (R,R)-2,3-dibromobutane(f)

Key Concepts

Chirality

Asymmetric Carbon Atoms

Meso Compounds

Watch next

Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.
(e) (R,R)-2,3-dibromobutane
(f)