{"id":818,"date":"2017-03-07T14:32:59","date_gmt":"2017-03-07T14:32:59","guid":{"rendered":"https:\/\/www.studyorgo.com\/blog\/?p=818"},"modified":"2017-03-07T15:36:05","modified_gmt":"2017-03-07T15:36:05","slug":"im-trying-to-figure-out-if-it-is-an-enantiomer-diastereomers-structural-isomer-or-meso-compound","status":"publish","type":"post","link":"https:\/\/www.studyorgo.com\/blog\/im-trying-to-figure-out-if-it-is-an-enantiomer-diastereomers-structural-isomer-or-meso-compound\/","title":{"rendered":"I’m trying to figure out if it is an enantiomer, diastereomers, structural isomer, or meso compound."},"content":{"rendered":"

\u201cI have two compounds that have the same substituents but they arranged different, I’m trying to figure out if it is an enantiomer, diastereomers, structural isomer, or meso compound.\u201d<\/em><\/p>\n

Here at StudyOrgo, we frequently get\u00a0questions about topics in organic chemistry that are usually quickly covered, poorly described or expected that you know from previous courses.\u00a0 These concepts are really important to understanding the more complex topics to come.\u00a0 In this article, we will cover the concepts of stereochemistry to review the basics and look at some specific examples.\u00a0 This is just a preview of the detailed topics and materials available\u00a0with your membership to StudyOrgo.com<\/a>.\u00a0 Sign up today!<\/p>\n

Structural isomers, or constitutional isomers, <\/strong>are molecules with the same chemical formula but different connectivity, they literally do not look alike.<\/p>\n

Stereoisomers<\/strong>\u00a0refer to molecules with the same chemical formula (i.e. same number of atoms) and geometrical arrangement (i.e. same connectivity) that are\u00a0not superimposable on each other<\/strong>. \u00a0They frequently will be described as “R” or “S” configuration<\/p>\n

\"cloro\"<\/a><\/p>\n

For a carbon center (referred to as a stereocenter), this requires bonding to four different substituents!\u00a0 If they are mirror images<\/u><\/strong>, they are\u00a0enantiomers<\/strong>.\u00a0 If they are\u00a0not mirror images<\/u><\/strong>, then they are\u00a0diastereomers<\/strong>.\u00a0 Remember, you can use R and S configuration can help distinguish this. \u00a0R,R would be the enantiomer of S,S. \u00a0But both R, S and S,R are the diastereomers of R,R.<\/p>\n

\"Screen<\/a><\/p>\n

\"Screen<\/a><\/p>\n

Compounds that contain stereocenters but have a plane of symmetry across them (such that they have a mirror image of itself somewhere<\/strong>) are referred to as meso compounds<\/strong>. Take a look at tartaric acid, it has two stereocenters but the blue box represents an axis of symmetry that makes the compound meso.<\/p>\n

\"meso\"<\/a><\/p>\n

 <\/p>\n

The usefulness of this is that proteins (the drug targets) are also chiral, so they need chiral drugs to affect them.\u00a0 If the compounds are not chiral, they will not interact with the proteins correctly.\u00a0 For synthesis, if the compounds are not chiral, they will not rotate plane polarized light, and will be called \u201coptically inactive\u201d.<\/p>\n

A few tips:<\/strong><\/p>\n

    \n
  1. If you only have one stereocenter then the non-superimposable, mirror image of the compound is the enantiomer.<\/li>\n
  2. In order to have diastereomers, you need more than one stereocenter.\u00a0 Sugars (saccharides) are the best example of this.\u00a0 Look at glucose, it has 4 stereocenters.\u00a0 The mirror image is the exact opposite configuration,\u00a0so there is only one enanantiomer for glucose, but there are 7 diastereomers!<\/li>\n
  3. Use the chart above to help you with R & S nomenclature and how that relates to enantiomers and diastereomers, this is how you will frequently encounter them after the first exam.<\/li>\n
  4. Look for planes of symmetry to identify meso compounds.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"

    \u201cI have two compounds that have the same substituents but they arranged different, I’m trying to figure out if it is an enantiomer, diastereomers, structural isomer, or meso compound.\u201d Here at StudyOrgo, we frequently get\u00a0questions about topics in organic chemistry that are usually quickly covered, poorly described or expected that you know from previous courses.\u00a0 […]<\/p>\n","protected":false},"author":7,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"footnotes":""},"categories":[1,12],"tags":[],"class_list":["post-818","post","type-post","status-publish","format-standard","hentry","category-organic-chemistry","category-q-and-a"],"aioseo_notices":[],"_links":{"self":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/818","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/users\/7"}],"replies":[{"embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/comments?post=818"}],"version-history":[{"count":4,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/818\/revisions"}],"predecessor-version":[{"id":824,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/818\/revisions\/824"}],"wp:attachment":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/media?parent=818"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/categories?post=818"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/tags?post=818"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}