{"id":6019,"date":"2020-10-13T12:48:00","date_gmt":"2020-10-13T07:18:00","guid":{"rendered":"http:\/\/astan.lk\/al_virtualclassroom\/?p=6019"},"modified":"2020-10-13T12:49:09","modified_gmt":"2020-10-13T07:19:09","slug":"alcohol","status":"publish","type":"post","link":"https:\/\/astan.lk\/al_virtualclassroom\/alcohol\/","title":{"rendered":"Alcohols"},"content":{"rendered":"<p>Monohydric alcohols can be classified into three types as primary, secondary and tertiary.<\/p>\n<p>Primary alcohols<\/p>\n<p><img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/primary.gif\" \/><\/p>\n<p>&nbsp;<\/p>\n<p>Secondary alcohols<\/p>\n<p><img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/secondary.gif\" \/><\/p>\n<p>&nbsp;<\/p>\n<p>Tertiary alcohols<\/p>\n<p><img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/tertiary.gif\" \/><\/p>\n<p>&nbsp;<\/p>\n<h4>Physical properties<\/h4>\n<p>In alcohols the \u2013OH bond is polarized as &#8211; R &#8211; O <sup>\u03b4-<\/sup> -H <sup>\u03b4+<\/sup> . Hence, due to the inter molecular hydrogen bonds formed between alcohol molecules, their boiling points have higher values compared to the alkanes and ether with comparable relative molecular masses. The boiling point increases in going down the series of alcohols.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/pp.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-10677\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/pp-300x108.png\" alt=\"\" width=\"300\" height=\"108\" \/><\/a><\/p>\n<p>The above diagram shows how the inter- molecular hydrogen bonds exist in ethanol. Alcohols which have low relative molecular mass are soluble in water. The solubility of alcohols in water is due to the \u2013 OH group which can forms H &#8211; bonds with water molecules. The non polar alkyl group in the alcohol molecule is a hindrance to the solubility in water. In going down the homologous series of alcohols the size of the non- polar alkyl group gradually increases relative to the \u2013OH group.<\/p>\n<p>&nbsp;<\/p>\n<h3>Reactions involving cleavage of the O-H bond<\/h3>\n<h4>(i) Reaction with sodium<\/h4>\n<p><img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/ethanolna.gif\" \/><\/p>\n<p>Alcohols behave as acids and react with sodium liberating hydrogen and forming sodium alkoxides. The alkoxide ion is a strong nucleophile and also a strong base.<\/p>\n<p>&nbsp;<\/p>\n<h4>(ii) Reaction with carboxylic acids (Acylation of alcohols)<\/h4>\n<p>Alcohols react with carboxylic acids to form esters. For this esterification reaction, concentrated H<sub>2<\/sub>SO<sub>4<\/sub> acid acts as a catalyst.<\/p>\n<p>The esterification reaction is both slow and reversible. The equation for the reaction between an acid RCOOH and an alcohol R&#8217;OH (where R and R&#8217; can be the same or different) is:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/padding.gif\" width=\"40\" height=\"15\" \/><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/estergeneq.gif\" width=\"358\" height=\"51\" \/><\/p>\n<p>So, for example, if you were making ethyl ethanoate from ethanoic acid and ethanol, the equation would be:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/padding.gif\" width=\"10\" height=\"15\" \/><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/ethetheqn.gif\" width=\"421\" height=\"52\" \/><\/p>\n<h3><\/h3>\n<h3>Nucleophilic substitution reactions that take place by the cleavage of C-O bond<\/h3>\n<h4>(i)Reaction with\u00a0PCl<sub>3<\/sub> or PCl<sub>5<\/sub><\/h4>\n<p>Alcohols react with PCl<sub>3<\/sub> or PCl<sub>5<\/sub> to give alkyl chlorides.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/rohpcl3eqn.gif\" width=\"457\" height=\"17\" \/><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/rohpcl5eqn.gif\" width=\"427\" height=\"15\" \/><\/p>\n<h4><\/h4>\n<h4>(ii) Reaction with hydrogen halides<\/h4>\n<p>&nbsp;<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ac1.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-10682\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ac1.png\" alt=\"\" width=\"230\" height=\"40\" \/><\/a><\/p>\n<p>Alcohols under go nucleophilic substitution reaction with HBr to give the corresponding alkyl bromides. Protonation of the O atom converts the -OH group into a better leaving group.<br \/>\n<a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ac.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-10683\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ac-300x106.png\" alt=\"\" width=\"300\" height=\"106\" \/><\/a>In this reaction Br- ion acts as a nucleophile and the leaving group is H2O.<\/p>\n<h4><\/h4>\n<h4>(iii) Reaction with anhydrous ZnCl<sub>2<\/sub> and conc. HCl (Lucas test)<\/h4>\n<p>In this reaction, R-OH is converted to R-Cl. ZnCl<sub>2<\/sub> is used as a catalyst. Because alkyl halides are insoluble in water, as the raction proceeds the reaction mixture becomes cloudy and turbid. The time taken for the turbidity to appear, after the mixing of reagents, can be used to distinguish between primary, secondary and tertiary alcohols.<\/p>\n<p>Under the provided reaction conditions the above nucleophilic substitution reaction takes place in two steps. Tertiary alcohols form stable intermediate tertiary carbocations and therefore, <strong>tertiary alcohols in the presence of the Lucas reagent forms a turbidity in a very short time. Secondary alcohols take longer time and primary alcohols react very slowly.<\/strong><\/p>\n<h4><\/h4>\n<h3>Elimination reactions<\/h3>\n<p>Alcohols undergo an elimination reaction when treated with conc. H<sub>2<\/sub>SO<sub>4<\/sub> or when heated with alumina to a higher temperature. The reaction in which a molecule of water is eliminated from an alcohol is the dehydration of alcohols. Here, an alkene is formed as the product of the reaction.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/alc.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-10686\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/alc-300x89.png\" alt=\"\" width=\"300\" height=\"89\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<h3>Oxidation of alcohols<\/h3>\n<p>The product of oxidation depends on primary, secondary or tertiary nature of the alcohol. Oxidation of alcohols can be carried out with H<sup>+<\/sup>\/KMnO<sub>4<\/sub> or H<sup>+<\/sup>\/K<sub>2<\/sub>Cr<sub>2<\/sub>O<sub>2<\/sub> or H<sup>+<\/sup>\/CrO<sub>3<\/sub>.<\/p>\n<p>&nbsp;<\/p>\n<p>(i) Primary alcohols<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alcohols\/makeacidsimple2.gif\" width=\"299\" height=\"56\" \/><\/p>\n<p>In the presence of the above mentioned oxidizing agents primary alcohols first give aldehydes. These are further oxidized to carboxylic acids. If pyridinium chlorochromate [C<sub>5<\/sub>H<sub>5<\/sub>NH<sup>+<\/sup>CrO<sub>3<\/sub>Cl] is used, the reaction can be stopped at the stage where aldehyde is formed.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/alcl.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-10687\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/alcl.png\" alt=\"\" width=\"259\" height=\"175\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<p>(ii) Secondary alcohols are oxidized to give ketones.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/alcl1.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-10688\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/alcl1.png\" alt=\"\" width=\"287\" height=\"75\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<p>(iii)Tertiary alcohols<br \/>\nNormally the tertiary alcohols do not undergo oxidation under conditions that primary and secondary alcohols are oxidized.<\/p>\n<p>&nbsp;<\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Monohydric alcohols can be classified into three types as primary, secondary and tertiary. Primary alcohols &nbsp; Secondary alcohols &nbsp; Tertiary alcohols &nbsp; Physical properties In alcohols the \u2013OH bond is polarized as &#8211; R &#8211; O \u03b4- -H \u03b4+ . Hence, due to the inter molecular hydrogen bonds formed between alcohol molecules, their boiling points [&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-6019","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>Alcohols - 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\/alcohol\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Alcohols - Learning &amp; Education Portal\" \/>\n<meta property=\"og:description\" content=\"Monohydric alcohols can be classified into three types as primary, secondary and tertiary. 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