{"id":6021,"date":"2020-10-13T12:47:01","date_gmt":"2020-10-13T07:17:01","guid":{"rendered":"http:\/\/astan.lk\/al_virtualclassroom\/?p=6021"},"modified":"2020-10-13T12:47:41","modified_gmt":"2020-10-13T07:17:41","slug":"phenol","status":"publish","type":"post","link":"https:\/\/astan.lk\/al_virtualclassroom\/phenol\/","title":{"rendered":"Phenol"},"content":{"rendered":"<p>Aromatic compounds, in which an -OH group is joined directly to a carbon atom of a benzene ring are called phenols. Alcohols and phenols dissociate in aqueous solutions as shown below.<\/p>\n<p>ROH + H<sub>2<\/sub>O <b><span class=\"content_color\"> <span id=\"MathJax-Element-6-Frame\" class=\"MathJax\" style=\"display: inline; font-style: normal; font-weight: normal; line-height: normal; font-size: 13px; text-indent: 0px; text-align: left; text-transform: none; letter-spacing: normal; word-spacing: normal; word-wrap: normal; white-space: nowrap; float: none; direction: ltr; max-width: none; max-height: none; min-width: 0px; min-height: 0px; border: 0px; padding: 0px; margin: 0px; position: relative;\" tabindex=\"0\" data-mathml=\"&lt;math xmlns=&quot;http:\/\/www.w3.org\/1998\/Math\/MathML&quot;&gt;&lt;mo class=&quot;MJX-variant&quot; stretchy=&quot;false&quot;&gt;&amp;#x21CC;&lt;\/mo&gt;&lt;\/math&gt;\"><span id=\"MathJax-Span-16\" class=\"math\"><span id=\"MathJax-Span-17\" class=\"mrow\"><span id=\"MathJax-Span-18\" class=\"mo\">\u21cc\u00a0<\/span><\/span><\/span><\/span><\/span><\/b>RO<sup>&#8211;<\/sup> + H<sub>3<\/sub>O<sup>+<\/sup><br \/>\n<img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/phenol\/phenolh2oeqm.gif\" \/><\/p>\n<p>Phenols are more acidic than alcohols. This means that in the above equilibria, the equilibrium point for phenols is more towards the right than alcohols. The reason for this is that the stability of phenate ion relative to phenol is greater than the stability of the alkoxide ion relative to the alcohol. The phenate ion is more stable because its negative charge gets delocalized by resonance. In the alkoxide ion there is no such charge dispersion.<\/p>\n<h3><\/h3>\n<h3>Reactions involving cleavage of the O-H bond<\/h3>\n<p>The higher acidity of phenols is confirmed by the following examples too. Although an alcohol reacts with sodium it does not react with NaOH. But phenol reacts with sodium as well as with NaOH. However, phenol is not acidic enough to react with Na<sub>2<\/sub>CO<sub>3<\/sub>.<\/p>\n<p>2 C<sub>6<\/sub>H<sub>5<\/sub>OH + 2Na \u2192 2C<sub>6<\/sub>H<sub>5<\/sub>O<sup>&#8211;<\/sup>\u00a0Na<sup>+<\/sup>+ H<sub>2<\/sub><\/p>\n<p><img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/phenol\/phenolnaoh.gif\" \/><\/p>\n<p>&nbsp;<\/p>\n<h4>Non occurance of nucleophilic substitution reactions by breaking C-O bond<\/h4>\n<p>Unlike alcohols phenols do not undergo nucleophilic substitution reactions because,<\/p>\n<p>(i) the C-O bond is shorter and stronger due to delocalization of lone pair of electrons<br \/>\non the oxygen atom into the benzene ring. This can be shown by resonance.<a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/alc12.png\"><br \/>\n<\/a><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"\" src=\"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/2\/2c\/Phenol_resonance.svg\/2000px-Phenol_resonance.svg.png\" width=\"498\" height=\"130\" \/><\/p>\n<p>(ii) phenyl cation is unstable.<\/p>\n<p>&nbsp;<\/p>\n<h3>The effect of the -OH group on the reactivity of the benzene ring in phenol.<\/h3>\n<p>\u2022 Due to the delocalization of the lone pairs of electrons which were on the oxygen atom with the benzene ring, the ring is rich with electrons. It has become very reactive towards electrophilic reagents. The O-H group of phenol is ortho, para directing. (It is not necessary to explain why the -OH group is ortho, para directing)<\/p>\n<p>\u2022 When the electrophilic substitution reactions of phenol are compared with the corresponding reactions of benzene along with the relevant conditions, it is clear that the benzene ring of phenol, had become more reactive towards electrophiles.<\/p>\n<p>Consider the following examples.<\/p>\n<p><strong>(i) Reacts immediately with bromine water to give a white precipitate of 2,4,6 \u2013 tribromophenol.<\/strong><\/p>\n<p><img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/phenol\/maketbp.gif\" \/><\/p>\n<p>&nbsp;<\/p>\n<p><strong>(ii) For nitration of phenol even dilute HNO<sub>3<\/sub> is sufficiently reactive.<\/strong><\/p>\n<p><b><i>With dilute nitric acid<\/i><\/b><\/p>\n<p>Phenol reacts with dilute nitric acid at room temperature to give a mixture of 2 nitrophenol and 4-nitrophenol.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/phenol\/padding.gif\" width=\"40\" height=\"15\" \/><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/phenol\/make2nitroph.gif\" width=\"370\" height=\"85\" \/><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/phenol\/padding.gif\" width=\"40\" height=\"15\" \/><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/phenol\/make4nitroph.gif\" width=\"346\" height=\"104\" \/><\/p>\n<p>&nbsp;<\/p>\n<p><b><i>With concentrated nitric acid<\/i><\/b><\/p>\n<p>With concentrated nitric acid, more nitro groups substitute around the ring to give 2,4,6-trinitrophenol<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/phenol\/padding.gif\" width=\"40\" height=\"15\" \/><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/phenol\/makepicric.gif\" width=\"366\" height=\"104\" \/><\/p>\n<p>&nbsp;<\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Aromatic compounds, in which an -OH group is joined directly to a carbon atom of a benzene ring are called phenols. Alcohols and phenols dissociate in aqueous solutions as shown below. ROH + H2O \u21cc\u00a0RO&#8211; + H3O+ Phenols are more acidic than alcohols. This means that in the above equilibria, the equilibrium point for phenols [&hellip;]<\/p>\n","protected":false},"author":842,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"footnotes":""},"categories":[14,1670],"tags":[],"class_list":["post-6021","post","type-post","status-publish","format-standard","hentry","category-chemistry","category-unit-10"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v26.9 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Phenol - Learning &amp; Education Portal<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/astan.lk\/al_virtualclassroom\/phenol\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Phenol - Learning &amp; Education Portal\" \/>\n<meta property=\"og:description\" content=\"Aromatic compounds, in which an -OH group is joined directly to a carbon atom of a benzene ring are called phenols. 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