{"id":37821,"date":"2025-06-26T06:30:56","date_gmt":"2025-06-26T06:30:56","guid":{"rendered":"https:\/\/gaviki.com\/blog\/?p=37821"},"modified":"2025-06-26T06:30:58","modified_gmt":"2025-06-26T06:30:58","slug":"consider-the-oxalate-ion-c2o4-2","status":"publish","type":"post","link":"https:\/\/gaviki.com\/blog\/consider-the-oxalate-ion-c2o4-2\/","title":{"rendered":"Consider the oxalate ion, C2O4^-2."},"content":{"rendered":"\n<p>Consider the oxalate ion, C2O4^-2. Draw the Lewis structure, including all equivalent resonance structures. Are all carbon-oxygen bonds the same in this ion? If so, give the bond order. If not, give the bond order for each unique bond. b) The oxalate ion is the anion of oxalic acid, H2C2O4, an oxo-acid. Oxalic acid is found in rhubarb leaves and is toxic. Draw the Lewis structure for oxalic acid. Are all carbon-oxygen bonds the same in this ion? If so, give the bond order. If not, give the bond order for each unique bond. c) Consider HC2O4^-. Draw the Lewis structure for oxalic acid. Are all carbon-oxygen bonds the same in this molecule? If so, give the bond order. If not, give the bond order for each unique bond<\/p>\n\n\n\n<p><strong><mark style=\"background-color:rgba(0, 0, 0, 0)\" class=\"has-inline-color has-vivid-cyan-blue-color\">The Correct Answer and Explanation is:<\/mark><\/strong><\/p>\n\n\n\n<h3 class=\"wp-block-heading\">a) <strong>Lewis Structure of Oxalate Ion (C\u2082O\u2084\u00b2\u207b)<\/strong><\/h3>\n\n\n\n<p>Oxalate ion has the formula C\u2082O\u2084\u00b2\u207b, with two carbon atoms and four oxygen atoms. Each carbon atom forms three bonds: one to another carbon and two to oxygens. The ion carries a total charge of \u22122.<\/p>\n\n\n\n<p>There are <strong>two major resonance structures<\/strong> where the negative charges are delocalized among the oxygen atoms. Each carbon is double-bonded to one oxygen and single-bonded to another, but in different patterns.<\/p>\n\n\n\n<p><strong>Resonance Structures:<\/strong><\/p>\n\n\n\n<pre class=\"wp-block-preformatted\">mathematicaCopyEdit<code>  O\u207b       O\n   \\       \/\/\n    C \u2014 C\n   \/\/       \\\n  O        O\u207b\n\n  O        O\u207b\n   \\\\       \/\n    C \u2014 C\n   \/       \\\\\n O\u207b        O\n<\/code><\/pre>\n\n\n\n<p><strong>Bond Order Analysis:<\/strong><\/p>\n\n\n\n<p>The carbon-oxygen bonds alternate between single and double in the resonance structures, but resonance causes the actual bond lengths to be equalized. Since each C\u2014O bond is either a single or double bond in different structures, and there are 4 C\u2014O bonds with 2 double bonds total across structures, the <strong>average bond order is 1.5<\/strong>. Therefore, <strong>all C\u2014O bonds are equivalent<\/strong> due to resonance, with a bond order of <strong>1.5<\/strong>.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">b) <strong>Lewis Structure of Oxalic Acid (H\u2082C\u2082O\u2084)<\/strong><\/h3>\n\n\n\n<p>Oxalic acid has two carboxylic acid groups: HO\u2013C(=O)\u2013C(=O)\u2013OH.<\/p>\n\n\n\n<p><strong>Structure:<\/strong><\/p>\n\n\n\n<pre class=\"wp-block-preformatted\">scssCopyEdit<code>HO\u2014C(=O)\u2014C(=O)\u2014OH\n<\/code><\/pre>\n\n\n\n<p>Each carbon is double bonded to one oxygen and single bonded to a hydroxyl group (\u2013OH). There are no equivalent resonance structures affecting the entire molecule like in the oxalate ion.<\/p>\n\n\n\n<p><strong>Bond Order Analysis:<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Each carbon has <strong>one C=O (double bond)<\/strong> and <strong>one C\u2013OH (single bond)<\/strong>.<\/li>\n\n\n\n<li>So, <strong>not all carbon\u2013oxygen bonds are the same<\/strong>.<\/li>\n\n\n\n<li>Bond order for C=O is <strong>2<\/strong>, and for C\u2013OH is <strong>1<\/strong>.<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">c) <strong>Lewis Structure of Hydrogen Oxalate Ion (HC\u2082O\u2084\u207b)<\/strong><\/h3>\n\n\n\n<p>This is the monoanion of oxalic acid. It contains one protonated carboxylic acid (COOH) and one deprotonated carboxylate (COO\u207b) group.<\/p>\n\n\n\n<p><strong>Structure:<\/strong><\/p>\n\n\n\n<pre class=\"wp-block-preformatted\">mathematicaCopyEdit<code>HO\u2014C(=O)\u2014C(\u2013O\u207b)=O\n<\/code><\/pre>\n\n\n\n<p>The carboxylate group (COO\u207b) has <strong>resonance<\/strong> between its two oxygen atoms, while the carboxylic acid group (COOH) does not.<\/p>\n\n\n\n<p><strong>Bond Order Analysis:<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>In COOH group: C=O is bond order 2, C\u2013OH is bond order 1.<\/li>\n\n\n\n<li>In COO\u207b group: both C\u2013O bonds are resonance-stabilized and have <strong>bond order 1.5<\/strong>.<\/li>\n<\/ul>\n\n\n\n<p>So, <strong>not all carbon\u2013oxygen bonds are the same<\/strong> in HC\u2082O\u2084\u207b:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>One C=O: bond order 2<\/li>\n\n\n\n<li>One C\u2013OH: bond order 1<\/li>\n\n\n\n<li>Two C\u2013O in COO\u207b group: bond order 1.5 each.<\/li>\n<\/ul>\n\n\n\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"852\" height=\"1024\" src=\"https:\/\/gaviki.com\/blog\/wp-content\/uploads\/2025\/06\/learnexams-banner8-980.jpeg\" alt=\"\" class=\"wp-image-37823\" srcset=\"https:\/\/gaviki.com\/blog\/wp-content\/uploads\/2025\/06\/learnexams-banner8-980.jpeg 852w, https:\/\/gaviki.com\/blog\/wp-content\/uploads\/2025\/06\/learnexams-banner8-980-250x300.jpeg 250w, https:\/\/gaviki.com\/blog\/wp-content\/uploads\/2025\/06\/learnexams-banner8-980-768x923.jpeg 768w\" sizes=\"auto, (max-width: 852px) 100vw, 852px\" \/><\/figure>\n","protected":false},"excerpt":{"rendered":"<p>Consider the oxalate ion, C2O4^-2. Draw the Lewis structure, including all equivalent resonance structures. Are all carbon-oxygen bonds the same in this ion? If so, give the bond order. If not, give the bond order for each unique bond. b) The oxalate ion is the anion of oxalic acid, H2C2O4, an oxo-acid. Oxalic acid is [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-37821","post","type-post","status-publish","format-standard","hentry","category-quiz-questions"],"_links":{"self":[{"href":"https:\/\/gaviki.com\/blog\/wp-json\/wp\/v2\/posts\/37821","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/gaviki.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/gaviki.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/gaviki.com\/blog\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/gaviki.com\/blog\/wp-json\/wp\/v2\/comments?post=37821"}],"version-history":[{"count":1,"href":"https:\/\/gaviki.com\/blog\/wp-json\/wp\/v2\/posts\/37821\/revisions"}],"predecessor-version":[{"id":37824,"href":"https:\/\/gaviki.com\/blog\/wp-json\/wp\/v2\/posts\/37821\/revisions\/37824"}],"wp:attachment":[{"href":"https:\/\/gaviki.com\/blog\/wp-json\/wp\/v2\/media?parent=37821"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/gaviki.com\/blog\/wp-json\/wp\/v2\/categories?post=37821"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/gaviki.com\/blog\/wp-json\/wp\/v2\/tags?post=37821"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}