{"id":1148,"date":"2017-10-19T13:14:21","date_gmt":"2017-10-19T13:14:21","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&p=1148"},"modified":"2018-10-05T17:38:52","modified_gmt":"2018-10-05T17:38:52","slug":"stereochemistry-of-reactions-addition-of-water-to-an-achiral-alkene","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/stereochemistry-of-reactions-addition-of-water-to-an-achiral-alkene\/","title":{"raw":"Stereochemistry of Reactions: Addition of Water to an Achiral Alkene","rendered":"Stereochemistry of Reactions: Addition of Water to an Achiral Alkene"},"content":{"raw":"
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Objectives<\/h3>\r\n
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\r\n\r\nAfter completing this section, you should be able to account for the stereochemistry of the product of the addition of water to an alkene in terms of the formation of a planar carbocation.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n
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Study Notes<\/h3>\r\nOrganic reactions in the laboratory or in living systems can produce chiral centres. Consider reaction of 1-butene with water (acid catalyzed). Markovnikov regiochemistry occurs and the OH adds to the second carbon. However, both R<\/em> and S<\/em> products occur giving a racemic (50\/50) mixture of 2\u2011butanol. How does this occur? The proton addition to 1\u2011butene results in a planar carbocation intermediate. A molecule of water is then equally likely to attack from the top or the bottom of this cation to produce either (S<\/em>)\u20112\u2011butanol or (R<\/em>)\u20112\u2011butanol, respectively.\"mechanism\r\n\r\n \r\n\r\n<\/div>\r\n<\/div>\r\n
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Contributors<\/h3>\r\n