- \n
- Remember in order to have chirality, molecules must have the following characteristics\n
- \n
- Carbon center with 4 unique substituents, meaning they are chemically distinguishable from each other.
\n![\"Carbon](\"http:\/\/www.studyorgo.com\/blog\/wp-content\/uploads\/2014\/12\/chiral.png\")
<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n- \n
- In this example, the molecule on the left has 3 red hydrogens.\u00a0 These hydrogens are chemically indistinguishable from each other.\u00a0 So the molecule is ACHIRAL.<\/li>\n
- The molecule on the right has 1 red hydrogen and 3 other unique substituents.\u00a0 Therefore, the molecule is CHIRAL.<\/li>\n<\/ul>\n
- Concept 2 \u2013 Chrial molecules that have STEREOISOMERS.<\/b>\n
- \n
- Stereoisomers are molecules that have the same chemical formula, but differ in their arrangement at a chiral center.
\n![\"Stereoisomers](\"http:\/\/www.studyorgo.com\/blog\/wp-content\/uploads\/2014\/12\/cloro.png\")
<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n- \n
- Concept 3 \u2013 Stereoisomers are identified by their \u201cHANDEDNESS<\/b>\u201d, which refers to the arrangement of the substituents relative to their importance.\n
- \n
- In general, elements of higher mass have higher priority.\u00a0 Refer to our tutorial on chirality for more details.
\n![\"left\"](\"http:\/\/www.studyorgo.com\/blog\/wp-content\/uploads\/2014\/12\/left.png\")
<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<\/p>\n
- \n
- Concept 4 \u2013 There are two types of STEREOISOMERS<\/b>, enantiomers and diastereomers.\n
- \n
- Enantiomers contain chiral centers that are non-superimposable & mirror images.\u00a0 They only come in pairs!<\/li>\n
- Diastereomers contain chiral centers are non-superimposable but are NOT mirror images.\u00a0 There can be many more than 2 depending on the number of stereocenters.<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n
An easy way to remember enantiomers from diastereomers is to memorize the picture below.\u00a0 In the case of 2 chiral centers, 4 stereoisomers are possible.\u00a0 Only the exact opposites (diagonal arrows) are enantiomers <\/b>and they therefore have a mirror image that is not superimposable.\u00a0 The molecules with only one stereocenter that differs (parallel arrows) are diastereomers. \u00a0<\/b><\/p>\n
![\"only](\"http:\/\/www.studyorgo.com\/blog\/wp-content\/uploads\/2014\/12\/Screen-Shot-2014-12-18-at-1.00.28-PM.png\")
<\/p>\nA biological example of this is saccharide (or sugar) chemistry and below is the enantiomers and diastereomers of threose.<\/p>\n
![\"A](\"http:\/\/www.studyorgo.com\/blog\/wp-content\/uploads\/2014\/12\/Screen-Shot-2014-12-18-at-1.00.18-PM.png\")
<\/p>\nWhile enantiomers can only come in pairs, many diastereomers can exist for a given molecule.\u00a0 Let\u2019s take, 5-DHT for example, the metabolically active form of testosterone.\u00a0 This molecule has 7 stereocenters, using the 2N<\/sup> rule for determining the number of stereoisomers, which gives 128 possible combinations. But only one of them is the enantiomer of 5DHT!\u00a0 The rest are diastereomers.<\/p>\n
![\"Screen](\"http:\/\/www.studyorgo.com\/blog\/wp-content\/uploads\/2014\/12\/Screen-Shot-2014-12-18-at-1.02.36-PM.png\")
<\/p>\nThis is just an example of the crystal-clear explanations you will receive as a member of StudyOrgo.com<\/a> about important, and often confusing and poorly explained, concepts in organic chemistry. Our site developers have listened to students\u2019 concerns and have come up with clear visuals to our tutorials on organic chemistry topics.\u00a0 Interested further?\u00a0 Sign up<\/a> today!<\/p>\n","protected":false},"excerpt":{"rendered":"
This is a problem that plagues many students studying organic chemistry and it is one of the cornerstones of getting through the class.\u00a0 Without a clear understanding of stereochemistry, determining the correct product for future reactions will be impossible, so let\u2019s break it down into some simple concepts. Concept 1 \u2013 in order to have […]<\/p>\n","protected":false},"author":1,"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],"tags":[],"class_list":["post-444","post","type-post","status-publish","format-standard","hentry","category-organic-chemistry"],"aioseo_notices":[],"_links":{"self":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/444","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\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/comments?post=444"}],"version-history":[{"count":3,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/444\/revisions"}],"predecessor-version":[{"id":455,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/444\/revisions\/455"}],"wp:attachment":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/media?parent=444"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/categories?post=444"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/tags?post=444"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}
- Concept 4 \u2013 There are two types of STEREOISOMERS<\/b>, enantiomers and diastereomers.\n
- In general, elements of higher mass have higher priority.\u00a0 Refer to our tutorial on chirality for more details.
- Concept 3 \u2013 Stereoisomers are identified by their \u201cHANDEDNESS<\/b>\u201d, which refers to the arrangement of the substituents relative to their importance.\n
- Stereoisomers are molecules that have the same chemical formula, but differ in their arrangement at a chiral center.
- \n
- Carbon center with 4 unique substituents, meaning they are chemically distinguishable from each other.