{"id":6010,"date":"2020-10-13T12:24:23","date_gmt":"2020-10-13T06:54:23","guid":{"rendered":"http:\/\/astan.lk\/al_virtualclassroom\/?p=6010"},"modified":"2020-10-13T12:37:22","modified_gmt":"2020-10-13T07:07:22","slug":"alkane-alkene-alkyne","status":"publish","type":"post","link":"https:\/\/astan.lk\/al_virtualclassroom\/alkane-alkene-alkyne\/","title":{"rendered":"Alkanes, Alkenes, Alkynes"},"content":{"rendered":"<h3><span style=\"text-decoration: underline;\">Alkanes<\/span><\/h3>\n<p>\u2022 In alkanes all the bonds are either C-C or C-H bonds. The polaritiy of those C-C and C-H bonds are low. Therefore, they do not react with common polar reagents (eg. OH<sup>&#8211;<\/sup> , CN<sup>&#8211;<\/sup> , H<sup>+<\/sup> ) under normal conditions.<\/p>\n<h4><strong><span style=\"text-decoration: underline;\">Chlorination <\/span><\/strong><\/h4>\n<p>Alkanes react with the reagents such as Cl<sub>2<\/sub> and Br<sub>2<\/sub> that undergo easy homolytic cleavage to generate free radicals.<\/p>\n<p>The mechanism of the chlorination of methane is given below.<\/p>\n<p>Initiation step<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/c.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-9536\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/c.png\" alt=\"\" width=\"245\" height=\"57\" \/><\/a><\/p>\n<p>Chain propagation steps<\/p>\n<p>The Cl. free radical generated in the initiation step abstracts a H atom from the methane molecule by homolysis of the C-H bond.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/c1.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-9534\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/c1.png\" alt=\"\" width=\"244\" height=\"44\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<p>The .CH<sub>3<\/sub> free radical then reacts with a Cl<sub>2<\/sub> molecule forming CH<sub>3<\/sub>Cl and generate<br \/>\nanother .Cl free radical which can continue the chain reaction.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/c2.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-9533\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/c2.png\" alt=\"\" width=\"223\" height=\"47\" \/><\/a><\/p>\n<p>Chain termination steps<br \/>\nCombination of free radicals in the reaction mixture to form stable molecules, results in the termination of chains.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/c3.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-9532\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/c3.png\" alt=\"\" width=\"232\" height=\"114\" \/><\/a><\/p>\n<h3><\/h3>\n<h3>Reactions of alkenes<\/h3>\n<p>\u2022 The loosely bound \u03c0 electron cloud which lies above and below the plane of the<br \/>\nethylene molecule is capable of attracting electrophilic reagents.<\/p>\n<p>\u2022 A molecule or an ion that can accept a pair of electrons is referred to as an electrophile.<\/p>\n<h4><\/h4>\n<h4>Addition of hydrogen halides<\/h4>\n<p>\u2022 Here, the hydrogen atom which is the electron deficient pole of HBr molecule acts as an electrophile and attacks the double bond. During these electrophilic addition reactions, intermediate carbocations are formed.<\/p>\n<p>&nbsp;<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"\" src=\"http:\/\/www.chemguide.co.uk\/mechanisms\/eladd\/ethhbreq1.GIF\" width=\"254\" height=\"20\" \/><\/p>\n<p>Stability of carbocations follows the following order.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ccs.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-9539\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ccs-300x110.png\" alt=\"\" width=\"300\" height=\"110\" \/><\/a><\/p>\n<p>\u2022 When alkyl groups are attached to the positively charged C atom of the carbocation, the stability of the cation increases. The reason for this is the release of electrons by the alkyl groups through C-C \u03c3\u00a0bonds towards the positively charged carbon atom to which they are attached. This results in spreading the positive charge thereby stabilizing the ion.<\/p>\n<p>\u2022 In the electrophilic addition reactions of hydrogen halides to asymmetric alkenes, two different carbocations can be formed after the bonding of the electrophile. Out of these the more stable carbocation forms more easily.<\/p>\n<p><img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alkenes\/propenehcl.gif\" \/><\/p>\n<p>&nbsp;<\/p>\n<p>\u2022 The more stable carbocation is obtained when the electrophile gets attached to the carbon atom to which the highest number of hydrogen atoms are attached.<\/p>\n<p>\u2022 After studying reactions of a large number of alkenes, this observation has been generalized as Markownikoff\u2019s rule.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"\" src=\"http:\/\/www.chemguide.co.uk\/mechanisms\/eladd\/ethhbrmech.GIF\" width=\"398\" height=\"103\" \/><\/p>\n<p>&nbsp;<\/p>\n<p>\u2022 Hydrogen bromide adds in the opposite way to this rule when there are peroxides in the reaction medium. The reason for this is that in the presence of peroxides the reaction of hydrogen bromide and the alkenes takes place via a free radical mechanism. It is not expected to describe this mechanism.<\/p>\n<p><img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alkenes\/propenehbr2.gif\" \/><\/p>\n<p>This change of the direction of addition (Anti-Markownikoff\u2019s addition) is not exhibited by the other hydrogen halides.<\/p>\n<p>&nbsp;<\/p>\n<h4>Addition of bromine to alkenes<\/h4>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/b.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-10883\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/b.png\" alt=\"\" width=\"278\" height=\"35\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<p><strong>Mechanism<\/strong><br \/>\n\u2022 When a molecule of Br<sub>2<\/sub> approaches the \u03c0 electron cloud of an alkene molecule, it gets polarized . The positive end of the dipole then reacts with the alkene, transferring a Br<sup>+<\/sup> \u00a0ion to it during the reaction (by heterolytic cleavage of the Br-Br bond) forming a cyclic bromonium ion.<\/p>\n<p>\u2022 In the second step of the reaction, a Br<sup>&#8211;<\/sup> ion acting as a nucleophile, forms a bond to one of the carbon atoms bonded to Br<sup>+<\/sup> . The bond formed by that carbon atom to Br<sup>+<\/sup>\u00a0 is broken during this step, giving an open chain structure again.<\/p>\n<p><img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/mechanisms\/eladd\/ethbr2mech2a.GIF\" \/><\/p>\n<p><img decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/mechanisms\/eladd\/ethbr2mech2b.GIF\" \/><\/p>\n<h4><\/h4>\n<h4>Addition of sulphuric acid to alkenes and the hydrolysis of the product obtained.<\/h4>\n<p>\u2022 Here, proton acts as an electrophile and HSO4<sup>&#8211;<\/sup> ion acts a nucleophile<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alkenes\/ethh2so4eq.gif\" width=\"337\" height=\"21\" \/><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alkenes\/ethhso4hydr.gif\" width=\"410\" height=\"25\" \/><\/p>\n<p>&nbsp;<\/p>\n<h4>Reaction of alkenes with cold alkaline KMnO<sub>4<\/sub><\/h4>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alkenes\/dioleqn4.gif\" width=\"423\" height=\"76\" \/><\/p>\n<h4><\/h4>\n<h4>Catalytic hydrogenation<\/h4>\n<p>eg-Ethene reacts with hydrogen in the presence of a finely divided nickel catalyst at a temperature of about 150\u00b0C. Ethane is produced.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alkenes\/padding.gif\" width=\"40\" height=\"15\" \/><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/www.chemguide.co.uk\/organicprops\/alkenes\/c2h4hydrog.gif\" width=\"236\" height=\"28\" \/><\/p>\n<p>&nbsp;<\/p>\n<h3>Reactions of alkynes<\/h3>\n<p>\u2022 Alkynes have two \u03c0 bonds which react independantly and undergo electrophilic addition reactions with reagents that add to alkenes.<\/p>\n<p>&nbsp;<\/p>\n<h4>Addition of bromine<\/h4>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ab.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-10889\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ab.png\" alt=\"\" width=\"291\" height=\"121\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<h4>Addition of hydrogen halides<\/h4>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ahh.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-10888\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ahh.png\" alt=\"\" width=\"280\" height=\"61\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<h4>Addition of water<\/h4>\n<p>\u2022 In the presence of Hg <sup>2+<\/sup> and dilute sulphuric acid, one molecule of water gets added on to alkynes.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/aw.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-10887\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/aw-300x45.png\" alt=\"\" width=\"393\" height=\"59\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<p>\u2022 The rapid rearrangement of the enol to the aldehyde is due to the high stability of \u00a0 \u00a0 \u00a0C = O.<\/p>\n<p>&nbsp;<\/p>\n<h4>Catalytic hydrogenation of alkynes<\/h4>\n<p>\u2022 In the presence of catalysts such as finely powdered Pt, Pd or Ni alkynes react with hydrogen to give alkanes. The reaction can be stopped at the intermediate alkene stage by using a Pd\/BaSO<sub>4<\/sub> catalyst poisoned by quinoline.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ahy.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-10891\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ahy-300x183.png\" alt=\"\" width=\"300\" height=\"183\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<p>\u2022 In the alkynes, H-C\u2261C-Hand R-C\u2261C-H the H attached to the C that forms the triple bond (terminal hydrogen) shows acidic properties. The acidic H in these alkynes can be displaced by metals.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/a.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-10892\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/a-300x109.png\" alt=\"\" width=\"347\" height=\"126\" \/><\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Alkanes \u2022 In alkanes all the bonds are either C-C or C-H bonds. The polaritiy of those C-C and C-H bonds are low. Therefore, they do not react with common polar reagents (eg. OH&#8211; , CN&#8211; , H+ ) under normal conditions. Chlorination Alkanes react with the reagents such as Cl2 and Br2 that undergo [&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":[14,1666],"tags":[],"class_list":["post-6010","post","type-post","status-publish","format-standard","hentry","category-chemistry","category-unit-08"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v26.9 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Alkanes, Alkenes, Alkynes - 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\/alkane-alkene-alkyne\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Alkanes, Alkenes, Alkynes - Learning &amp; Education Portal\" \/>\n<meta property=\"og:description\" content=\"Alkanes \u2022 In alkanes all the bonds are either C-C or C-H bonds. 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