{"id":743,"date":"2017-10-24T14:25:22","date_gmt":"2017-10-24T14:25:22","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=743"},"modified":"2017-10-24T14:25:22","modified_gmt":"2017-10-24T14:25:22","slug":"enantiomers-and-the-tetrahedral-carbon","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/enantiomers-and-the-tetrahedral-carbon\/","title":{"raw":"Enantiomers and the Tetrahedral Carbon","rendered":"Enantiomers and the Tetrahedral Carbon"},"content":{"raw":"<div class=\"elm-header\">\r\n<div class=\"elm-header-custom\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Objectives<\/h3>\r\n<div class=\"elm-header\"><\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<div id=\"skills\">\r\n\r\nAfter completing this section, you should be able to\r\n<ol>\r\n \t<li>use molecular models to show that only a tetrahedral carbon atom satisfactorily accounts for the lack of isomerism in molecules of the type CH<sub>2<\/sub>XY, and for the existence of optical isomerism in molecules of the type CHXYZ.<\/li>\r\n \t<li>determine whether two differently oriented wedge-and-broken-line structures are identical or represent a pair of enantiomers.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<div>\r\n<div class=\"textbox key-takeaways\">\r\n<h3>Key Term<\/h3>\r\nMake certain that you can define, and use in context, the key term below.\r\n<ul>\r\n \t<li>enantiomer<\/li>\r\n<\/ul>\r\n<\/div>\r\n<div class=\"textbox\">\r\n<div id=\"note\">\r\n<h3 class=\"boxtitle\">Study Notes<\/h3>\r\nStereoisomers are isomers that differ in spatial arrangement of atoms, rather than order of atomic connectivity. One of their most interesting type of isomer is the mirror-image stereoisomers, a non-superimposable set of two molecules that are mirror image of one another. The existance of these molecules are determined by concept known as <strong>chirality<\/strong>. The word \u201cchiral\u201d was derived from the Greek word for hand, because our hands display a good example of chirality since they are non-superimposable mirror images of each other.\r\n\r\n<\/div>\r\n<\/div>\r\n\r\n\r\n<\/div>\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Introduction<\/h3>\r\n<p class=\"paragraph\">The opposite of chiral is <strong class=\"bold\">achiral<\/strong>. Achiral objects are superimposable with their mirror images. For example, two pieces of paper are achiral. In contrast, chiral molecules, like our hands, are non superimposable\u00a0mirror images of each other. Try to line up your left hand perfectly\u00a0with your right hand, so that the palms are both facing in the same directions.\u00a0Spend\u00a0about a minute doing this. Do you see that they cannot line up exactly?\u00a0\u00a0 The same thing applies to some\u00a0molecules<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05131441\/Chirality_with_hands.jpg\" alt=\"Chirality_with_hands.jpg\" width=\"250px\" height=\"170px\" \/>\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 <img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05131443\/Axial_chirality_of_spiro_compound.png\" alt=\"Axial_chirality_of_spiro_compound.png\" width=\"288px\" height=\"176px\" \/><\/p>\r\n<p class=\"paragraph\">A Chiral molecule has a\u00a0mirror image that cannot line up\u00a0with it perfectly- the mirror images are non superimposable. The mirror images are called <a title=\"Enantiomers\" href=\"\/Organic_Chemistry\/UMM_chemwiki_project\/Conformation_and_Stereochemistry\/Enantiomers\" rel=\"internal\"><strong class=\"bold\">enantiomers<\/strong><\/a>. But why are chiral molecules so interesting? A chiral molecule and its enantiomer have the same chemical and physical\u00a0properties(boiling point, melting point,polarity, density\u00a0etc...). It turns out that many of our biological molecules such as our DNA, amino acids and sugars, are chiral molecules.<\/p>\r\n<p class=\"paragraph\">It is pretty interesting that our hands seem to serve the same purpose but most people are only able to use one of their hands to write. Similarily this is true with chiral biological molecules and interactions. Just like your left\u00a0hand will not fit properly in your\u00a0right glove, one of the enantiomers of a molecule may not work the same way in your body.<\/p>\r\n<p class=\"paragraph\">This must mean that enantiomers have properties that\u00a0make them unique to their mirror images. One\u00a0of these\u00a0properties is that\u00a0they cannot have a <strong class=\"bold\">plan<\/strong><strong class=\"bold\">e of<\/strong><strong class=\"bold\"> <a class=\"internal\" title=\"Physical Chemistry\/Symmetry\" href=\"\/Physical_Chemistry\/Symmetry\" rel=\"internal\">symmetry<\/a><\/strong> or an internal mirror plane. So, a chiral\u00a0molecule\u00a0cannot be divided in two\u00a0mirror image halves. Another property of chiral molecules\u00a0is optical activity.<\/p>\r\nOrganic compounds, molecules created around a chain of carbon atom (more commonly known as carbon backbone), play an essential role in the chemistry of life. These molecules derive their importance from the energy they carry, mainly in a form of potential energy between atomic molecules. Since such potential force can be widely affected due to changes in atomic placement, it is important to understand the concept of an <a class=\"internal\" title=\"Inorganic Chemistry\/Descriptive Chemistry\/Transition Metals and Coordination Complexes\/Coordination Chemistry\/Isomers\" href=\"https:\/\/chem.libretexts.org\/Core\/Inorganic_Chemistry\/Coordination_Chemistry\/Properties_of_Coordination_Compounds\/Isomers\" rel=\"internal\">isomer<\/a>, a molecule sharing same atomic make up as another but differing in structural arrangements. This article will be devoted to a specific isomers called stereoisomers and its property of <a title=\"Organic Chemistry\/Chirality\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Chirality\" rel=\"internal\">chirality<\/a> (Figure 5.1.1).\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"353\"]<img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05131445\/molecule.png\" alt=\"\" width=\"353\" height=\"162\" \/> Figure 1. Two enantiomers of a tetrahedral complex. Image used with permission from Wikipedia[\/caption]\r\n\r\n\r\n<div>\r\n\r\nThe concepts of steroisomerism and chirality command great deal of importance in modern <a title=\"Organic Chemistry\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\" rel=\"internal\">organic chemistry<\/a>, as these ideas helps to understand the physical and theoretical reasons behind the formation and structures of numerous organic molecules, the main reason behind the energy embedded in these essential chemicals. In contrast to more well-known constitutional isomerism, which develops isotopic compounds simply by different atomic connectivity, stereoisomerism generally maintains equal atomic connections and orders of building blocks as well as having same numbers of atoms and types of elements.\r\n\r\nWhat, then, makes stereoisomers so unique? To answer this question, the learner must be able to think and imagine in not just two-dimensional images, but also three-dimensional space. This is due to the fact that stereoisomers are isomers because their atoms are different from others in terms of spatial arrangement.\r\n<div id=\"section_2\">\r\n\r\n\r\n<h3 class=\"editable\">Spatial Arrangement<\/h3>\r\nFirst and foremost, one must understand the concept of spatial arrangement in order to understand stereoisomerism and chirality. Spatial arrangement of atoms concern how different atomic particles and molecules are situated about in the space around the organic compound, namely its carbon chain. In this sense, spatial arrangement of an organic molecule are different another if an atom is shifted in any three-dimensional direction by even one degree. This opens up a very broad possibility of different molecules, each with their unique placement of atoms in three-dimensional space .\r\n\r\n<\/div>\r\n<div id=\"section_3\">\r\n\r\n\r\n<h3 class=\"editable\">Stereoisomers<\/h3>\r\n<a title=\"Organic Chemistry\/Virtual Textbook of OChem\/Stereoisomers\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Chirality\/Stereoisomers\" rel=\"internal\">Stereoisomers <\/a>are, as mentioned above, contain different types of isomers within itself, each with distinct characteristics that further separate each other as different chemical entities having different properties. Type called entaniomer are the previously-mentioned mirror-image stereoisomers, and will be explained in detail in this article. Another type, diastereomer, has different properties and will be introduced afterwards.\r\n<div id=\"section_4\">\r\n\r\n\r\n<h4 class=\"editable\">Enantiomers<\/h4>\r\nThis type of stereoisomer is the essential mirror-image, non-superimposable type of stereoisomer introduced in the beginning of the article. Figure 3 provides a perfect example; note that the gray plane in the middle demotes the mirror plane.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"396\"]<img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05131447\/Figure_3a.jpg\" alt=\"\" width=\"396\" height=\"304\" \/> Figure 2.[\/caption]\r\n\r\nNote that even if one were to flip over the left molecule over to the right, the atomic spatial arrangement will not be equal. This is equivalent to the left hand - right hand relationship, and is aptly referred to as 'handedness' in molecules. This can be somewhat counter-intuitive, so this article recommends the reader try the 'hand' example. Place both palm facing up, and hands next to each other. Now flip either side over to the other. One hand should be showing the back of the hand, while the other one is showing the palm. They are not same and non-superimposable. This is where the concept of chirality comes in as one of the most essential and defining idea of stereoisomerism.\r\n\r\n<\/div>\r\n<div id=\"section_5\">\r\n\r\n\r\n<h4 class=\"editable\">Chirality<\/h4>\r\n<a title=\"Organic Chemistry\/Chirality\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Chirality\" rel=\"internal\">Chirality<\/a> essentially means 'mirror-image, non-superimposable molecules', and to say that a molecule is chiral is to say that its mirror image (it must have one) is not the same as it self. Whether a molecule is chiral or achiral depends upon a certain set of overlapping conditions. Figure 5.1.1 shows an example of two molecules, chiral and achiral, respectively. Notice the distinct characteristic of the achiral molecule: it possesses two atoms of same element. In theory and reality, if one were to create a plane that runs through the other two atoms, they will be able to create what is known as bisecting plane: The images on either side of the plan is the same as the other (Figure 5.1.3).\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"263\"]<img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05131449\/Figure_4.jpg\" alt=\"Figure 4.jpg\" width=\"263\" height=\"277\" \/> Figure 3.[\/caption]\r\n\r\n\r\n\r\nIn this case, the molecule is considered 'achiral'. In other words, to distinguish chiral molecule from an achiral molecule, one must search for the existence of the bisecting plane in a molecule. All chiral molecules are deprive of bisecting plane, whether simple or complex. As a universal rule, no molecule with different surrounding atoms are achiral. Chirality is a simple but essential idea to support the concept of stereoisomerism, being used to explain one type of its kind. The chemical properties of the chiral molecule differs from its mirror image, and in this lies the significance of chilarity in relation to modern organic chemistry.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_6\">\r\n\r\n\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\r\n \t<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\r\n \t<li>William Reusch, Professor Emeritus (<a class=\"external\" title=\"http:\/\/www.msu.edu\/\" href=\"http:\/\/www.msu.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Michigan State U.<\/a>), <a class=\"external\" title=\"http:\/\/www.cem.msu.edu\/~reusch\/VirtualText\/intro1.htm\" href=\"http:\/\/www.cem.msu.edu\/%7Ereusch\/VirtualText\/intro1.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Virtual Textbook of\u00a0Organic\u00a0Chemistry<\/a><\/li>\r\n \t<li><a title=\"Organic_Chemistry_With_a_Biological_Emphasis\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\" rel=\"internal\">Organic Chemistry With a Biological Emphasis <\/a>by\u00a0<a class=\"external\" title=\"http:\/\/facultypages.morris.umn.edu\/~soderbt\/\" href=\"http:\/\/facultypages.morris.umn.edu\/%7Esoderbt\/\" target=\"_blank\" rel=\"external nofollow noopener\">Tim Soderberg<\/a>\u00a0(University of Minnesota, Morris)<\/li>\r\n \t<li>Jim Clark (<a class=\"external\" title=\"http:\/\/www.chemguide.co.uk\" href=\"http:\/\/www.chemguide.co.uk\" target=\"_blank\" rel=\"external nofollow noopener\">Chemguide.co.uk<\/a>)<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>","rendered":"<div class=\"elm-header\">\n<div class=\"elm-header-custom\">\n<div class=\"textbox learning-objectives\">\n<h3>Objectives<\/h3>\n<div class=\"elm-header\"><\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<div id=\"skills\">\n<p>After completing this section, you should be able to<\/p>\n<ol>\n<li>use molecular models to show that only a tetrahedral carbon atom satisfactorily accounts for the lack of isomerism in molecules of the type CH<sub>2<\/sub>XY, and for the existence of optical isomerism in molecules of the type CHXYZ.<\/li>\n<li>determine whether two differently oriented wedge-and-broken-line structures are identical or represent a pair of enantiomers.<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<div>\n<div class=\"textbox key-takeaways\">\n<h3>Key Term<\/h3>\n<p>Make certain that you can define, and use in context, the key term below.<\/p>\n<ul>\n<li>enantiomer<\/li>\n<\/ul>\n<\/div>\n<div class=\"textbox\">\n<div id=\"note\">\n<h3 class=\"boxtitle\">Study Notes<\/h3>\n<p>Stereoisomers are isomers that differ in spatial arrangement of atoms, rather than order of atomic connectivity. One of their most interesting type of isomer is the mirror-image stereoisomers, a non-superimposable set of two molecules that are mirror image of one another. The existance of these molecules are determined by concept known as <strong>chirality<\/strong>. The word \u201cchiral\u201d was derived from the Greek word for hand, because our hands display a good example of chirality since they are non-superimposable mirror images of each other.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_1\">\n<h3 class=\"editable\">Introduction<\/h3>\n<p class=\"paragraph\">The opposite of chiral is <strong class=\"bold\">achiral<\/strong>. Achiral objects are superimposable with their mirror images. For example, two pieces of paper are achiral. In contrast, chiral molecules, like our hands, are non superimposable\u00a0mirror images of each other. Try to line up your left hand perfectly\u00a0with your right hand, so that the palms are both facing in the same directions.\u00a0Spend\u00a0about a minute doing this. Do you see that they cannot line up exactly?\u00a0\u00a0 The same thing applies to some\u00a0molecules<\/p>\n<p class=\"paragraph\"><img decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05131441\/Chirality_with_hands.jpg\" alt=\"Chirality_with_hands.jpg\" width=\"250px\" height=\"170px\" \/>\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 <img decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05131443\/Axial_chirality_of_spiro_compound.png\" alt=\"Axial_chirality_of_spiro_compound.png\" width=\"288px\" height=\"176px\" \/><\/p>\n<p class=\"paragraph\">A Chiral molecule has a\u00a0mirror image that cannot line up\u00a0with it perfectly- the mirror images are non superimposable. The mirror images are called <a title=\"Enantiomers\" href=\"\/Organic_Chemistry\/UMM_chemwiki_project\/Conformation_and_Stereochemistry\/Enantiomers\" rel=\"internal\"><strong class=\"bold\">enantiomers<\/strong><\/a>. But why are chiral molecules so interesting? A chiral molecule and its enantiomer have the same chemical and physical\u00a0properties(boiling point, melting point,polarity, density\u00a0etc&#8230;). It turns out that many of our biological molecules such as our DNA, amino acids and sugars, are chiral molecules.<\/p>\n<p class=\"paragraph\">It is pretty interesting that our hands seem to serve the same purpose but most people are only able to use one of their hands to write. Similarily this is true with chiral biological molecules and interactions. Just like your left\u00a0hand will not fit properly in your\u00a0right glove, one of the enantiomers of a molecule may not work the same way in your body.<\/p>\n<p class=\"paragraph\">This must mean that enantiomers have properties that\u00a0make them unique to their mirror images. One\u00a0of these\u00a0properties is that\u00a0they cannot have a <strong class=\"bold\">plan<\/strong><strong class=\"bold\">e of<\/strong><strong class=\"bold\"> <a class=\"internal\" title=\"Physical Chemistry\/Symmetry\" href=\"\/Physical_Chemistry\/Symmetry\" rel=\"internal\">symmetry<\/a><\/strong> or an internal mirror plane. So, a chiral\u00a0molecule\u00a0cannot be divided in two\u00a0mirror image halves. Another property of chiral molecules\u00a0is optical activity.<\/p>\n<p>Organic compounds, molecules created around a chain of carbon atom (more commonly known as carbon backbone), play an essential role in the chemistry of life. These molecules derive their importance from the energy they carry, mainly in a form of potential energy between atomic molecules. Since such potential force can be widely affected due to changes in atomic placement, it is important to understand the concept of an <a class=\"internal\" title=\"Inorganic Chemistry\/Descriptive Chemistry\/Transition Metals and Coordination Complexes\/Coordination Chemistry\/Isomers\" href=\"https:\/\/chem.libretexts.org\/Core\/Inorganic_Chemistry\/Coordination_Chemistry\/Properties_of_Coordination_Compounds\/Isomers\" rel=\"internal\">isomer<\/a>, a molecule sharing same atomic make up as another but differing in structural arrangements. This article will be devoted to a specific isomers called stereoisomers and its property of <a title=\"Organic Chemistry\/Chirality\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Chirality\" rel=\"internal\">chirality<\/a> (Figure 5.1.1).<\/p>\n<div style=\"width: 363px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05131445\/molecule.png\" alt=\"\" width=\"353\" height=\"162\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 1. Two enantiomers of a tetrahedral complex. Image used with permission from Wikipedia<\/p>\n<\/div>\n<div>\n<p>The concepts of steroisomerism and chirality command great deal of importance in modern <a title=\"Organic Chemistry\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\" rel=\"internal\">organic chemistry<\/a>, as these ideas helps to understand the physical and theoretical reasons behind the formation and structures of numerous organic molecules, the main reason behind the energy embedded in these essential chemicals. In contrast to more well-known constitutional isomerism, which develops isotopic compounds simply by different atomic connectivity, stereoisomerism generally maintains equal atomic connections and orders of building blocks as well as having same numbers of atoms and types of elements.<\/p>\n<p>What, then, makes stereoisomers so unique? To answer this question, the learner must be able to think and imagine in not just two-dimensional images, but also three-dimensional space. This is due to the fact that stereoisomers are isomers because their atoms are different from others in terms of spatial arrangement.<\/p>\n<div id=\"section_2\">\n<h3 class=\"editable\">Spatial Arrangement<\/h3>\n<p>First and foremost, one must understand the concept of spatial arrangement in order to understand stereoisomerism and chirality. Spatial arrangement of atoms concern how different atomic particles and molecules are situated about in the space around the organic compound, namely its carbon chain. In this sense, spatial arrangement of an organic molecule are different another if an atom is shifted in any three-dimensional direction by even one degree. This opens up a very broad possibility of different molecules, each with their unique placement of atoms in three-dimensional space .<\/p>\n<\/div>\n<div id=\"section_3\">\n<h3 class=\"editable\">Stereoisomers<\/h3>\n<p><a title=\"Organic Chemistry\/Virtual Textbook of OChem\/Stereoisomers\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Chirality\/Stereoisomers\" rel=\"internal\">Stereoisomers <\/a>are, as mentioned above, contain different types of isomers within itself, each with distinct characteristics that further separate each other as different chemical entities having different properties. Type called entaniomer are the previously-mentioned mirror-image stereoisomers, and will be explained in detail in this article. Another type, diastereomer, has different properties and will be introduced afterwards.<\/p>\n<div id=\"section_4\">\n<h4 class=\"editable\">Enantiomers<\/h4>\n<p>This type of stereoisomer is the essential mirror-image, non-superimposable type of stereoisomer introduced in the beginning of the article. Figure 3 provides a perfect example; note that the gray plane in the middle demotes the mirror plane.<\/p>\n<div style=\"width: 406px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05131447\/Figure_3a.jpg\" alt=\"\" width=\"396\" height=\"304\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 2.<\/p>\n<\/div>\n<p>Note that even if one were to flip over the left molecule over to the right, the atomic spatial arrangement will not be equal. This is equivalent to the left hand &#8211; right hand relationship, and is aptly referred to as &#8216;handedness&#8217; in molecules. This can be somewhat counter-intuitive, so this article recommends the reader try the &#8216;hand&#8217; example. Place both palm facing up, and hands next to each other. Now flip either side over to the other. One hand should be showing the back of the hand, while the other one is showing the palm. They are not same and non-superimposable. This is where the concept of chirality comes in as one of the most essential and defining idea of stereoisomerism.<\/p>\n<\/div>\n<div id=\"section_5\">\n<h4 class=\"editable\">Chirality<\/h4>\n<p><a title=\"Organic Chemistry\/Chirality\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Chirality\" rel=\"internal\">Chirality<\/a> essentially means &#8216;mirror-image, non-superimposable molecules&#8217;, and to say that a molecule is chiral is to say that its mirror image (it must have one) is not the same as it self. Whether a molecule is chiral or achiral depends upon a certain set of overlapping conditions. Figure 5.1.1 shows an example of two molecules, chiral and achiral, respectively. Notice the distinct characteristic of the achiral molecule: it possesses two atoms of same element. In theory and reality, if one were to create a plane that runs through the other two atoms, they will be able to create what is known as bisecting plane: The images on either side of the plan is the same as the other (Figure 5.1.3).<\/p>\n<div style=\"width: 273px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05131449\/Figure_4.jpg\" alt=\"Figure 4.jpg\" width=\"263\" height=\"277\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 3.<\/p>\n<\/div>\n<p>In this case, the molecule is considered &#8216;achiral&#8217;. In other words, to distinguish chiral molecule from an achiral molecule, one must search for the existence of the bisecting plane in a molecule. All chiral molecules are deprive of bisecting plane, whether simple or complex. As a universal rule, no molecule with different surrounding atoms are achiral. Chirality is a simple but essential idea to support the concept of stereoisomerism, being used to explain one type of its kind. The chemical properties of the chiral molecule differs from its mirror image, and in this lies the significance of chilarity in relation to modern organic chemistry.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_6\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\n<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\n<li>William Reusch, Professor Emeritus (<a class=\"external\" title=\"http:\/\/www.msu.edu\/\" href=\"http:\/\/www.msu.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Michigan State U.<\/a>), <a class=\"external\" title=\"http:\/\/www.cem.msu.edu\/~reusch\/VirtualText\/intro1.htm\" href=\"http:\/\/www.cem.msu.edu\/%7Ereusch\/VirtualText\/intro1.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Virtual Textbook of\u00a0Organic\u00a0Chemistry<\/a><\/li>\n<li><a title=\"Organic_Chemistry_With_a_Biological_Emphasis\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\" rel=\"internal\">Organic Chemistry With a Biological Emphasis <\/a>by\u00a0<a class=\"external\" title=\"http:\/\/facultypages.morris.umn.edu\/~soderbt\/\" href=\"http:\/\/facultypages.morris.umn.edu\/%7Esoderbt\/\" target=\"_blank\" rel=\"external nofollow noopener\">Tim Soderberg<\/a>\u00a0(University of Minnesota, Morris)<\/li>\n<li>Jim Clark (<a class=\"external\" title=\"http:\/\/www.chemguide.co.uk\" href=\"http:\/\/www.chemguide.co.uk\" target=\"_blank\" rel=\"external nofollow noopener\">Chemguide.co.uk<\/a>)<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n","protected":false},"author":44985,"menu_order":2,"template":"","meta":{"_candela_citation":"[]","CANDELA_OUTCOMES_GUID":"","pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-743","chapter","type-chapter","status-publish","hentry"],"part":22,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/743","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/users\/44985"}],"version-history":[{"count":3,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/743\/revisions"}],"predecessor-version":[{"id":2070,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/743\/revisions\/2070"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/22"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/743\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=743"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=743"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=743"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=743"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}