Comments on: Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/ Mon, 19 Feb 2024 21:48:27 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers | Straight A Mindset https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/#comment-679080 Thu, 07 Dec 2023 23:22:36 +0000 https://www.masterorganicchemistry.com/?p=11745#comment-679080 […] Types Of Isomers: Constitutional Isomers Have Different Connectivites […]

]]>
By: Isomer: Definition, Types, Structures, and Examples https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/#comment-668197 Thu, 24 Aug 2023 13:10:51 +0000 https://www.masterorganicchemistry.com/?p=11745#comment-668197 […] Masterorganicchemistry.com […]

]]>
By: Best 21 What Is The Relationship Between The Following Two Molecules - Học Điện Tử Cơ Bản https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/#comment-638356 Sun, 18 Sep 2022 16:20:43 +0000 https://www.masterorganicchemistry.com/?p=11745#comment-638356 […] Quote from the source: … […]

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/#comment-636620 Mon, 29 Aug 2022 22:46:31 +0000 https://www.masterorganicchemistry.com/?p=11745#comment-636620 In reply to Eric Duan.

Ah yes. I apologize for giving you the too-simple answer.

The melting points of pure (+) or pure (-) enantiomers should be equal and opposite. Think about stacking a group of identical left- or right- shoes; they interact with each other in a similar way. We call these “homochiral” interactionss. But throw the enantiomer in there and you will have a combination of “homochiral” and “heterochiral” interactions. For example D-tartaric acid is going to hydrogen bond in a slightly different way with another molecule of D-tartaric acid than it will with L-tartaric acid.
The melting point of a mixture tends to be lower for this reason because stacking isn’t efficient.

But it gets more complicated. There are two major ways of forming a solid racemic mixture. You can have crystals which have unit cells containing both the (+)- and (-) enantiomers. This happens about 90% of the time. Or you can have crystals where the (+) and (-) forms crystallize only with each other (like Pasteur observed with potassium sodium tartrate). This is called a conglomerate. These situations will have different melting points as well. They can even be interconverted sometimes upon heating (2-binapthol is a prominent example).

For more detail I highly recommend the bible of stereochemistry, Eliel’s Stereochemistry of Organic Compounds. Page 155 of the edition that I have has a very clear discussion of this topic.

]]>
By: Eric Duan https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/#comment-636420 Sat, 27 Aug 2022 14:26:48 +0000 https://www.masterorganicchemistry.com/?p=11745#comment-636420 I checked the Wikipedia page for racemic mixtures, and it states that “In contrast to the two pure enantiomers, which have identical physical properties except for the direction of rotation of plane-polarized light, a racemate sometimes has different properties from either of the pure enantiomers. Different melting points are most common, but different solubilities and boiling points are also possible.” I’m just confused about what causes these different properties.
Link to the article: https://en.wikipedia.org/wiki/Racemic_mixture#cite_note-4:~:text=In%20contrast%20to,are%20also%20possible.

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/#comment-636399 Sat, 27 Aug 2022 08:06:53 +0000 https://www.masterorganicchemistry.com/?p=11745#comment-636399 In reply to Eric Duan.

Hi Eric – have you seen this post – https://www.masterorganicchemistry.com/2012/05/23/whats-a-racemic-mixture/
The only physical difference is in the direction in which they rotate plane-polarized light, and in how they interact with a chiral environment.

]]>
By: Eric Duan https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/#comment-636365 Fri, 26 Aug 2022 21:02:02 +0000 https://www.masterorganicchemistry.com/?p=11745#comment-636365 Hey James, this was a nicely detailed article and I found it quite understandable. I just had a quick question: Why does a racemic mixture have different properties than either of the pure compounds? If both enantiomers have the same physical properties, and the racemic mixture is just equal amounts of both enantiomers, where does the difference arise?
Thanks so much!

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/#comment-635978 Mon, 22 Aug 2022 16:07:40 +0000 https://www.masterorganicchemistry.com/?p=11745#comment-635978 In reply to Kabir.

Sometimes identical molecules are put in as “trick questions”. It’s easy to make identical molecules look superficially different by performing bond rotations or by using a different type of bond projection.

]]>
By: Kabir https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/#comment-635792 Sat, 20 Aug 2022 15:29:54 +0000 https://www.masterorganicchemistry.com/?p=11745#comment-635792 Sir put more examples of identical molecule?
Identical and same molecule is same or different concept?
One more request is show fisher to dash wedge formula in simple way.
Thanks.

]]>
By: how many unique stereoisomers are possible for the lsd molecule? https://www.masterorganicchemistry.com/2018/09/10/types-of-isomers/#comment-629220 Sun, 05 Jun 2022 17:02:30 +0000 https://www.masterorganicchemistry.com/?p=11745#comment-629220 […] these two stereoisomers enantiomers or diastereomers (and what does that […]

]]>