{"id":1154,"date":"2017-10-19T13:13:16","date_gmt":"2017-10-19T13:13:16","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&p=1154"},"modified":"2018-10-05T17:40:09","modified_gmt":"2018-10-05T17:40:09","slug":"stereochemistry-of-reactions-addition-of-water-to-a-chiral-alkene","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/stereochemistry-of-reactions-addition-of-water-to-a-chiral-alkene\/","title":{"raw":"Stereochemistry of Reactions: Addition of Water to a Chiral Alkene","rendered":"Stereochemistry of Reactions: Addition of Water to a Chiral Alkene"},"content":{"raw":"
\r\n
\r\n
\r\n

Objectives<\/h3>\r\n
\r\n
\r\n
\r\n\r\nAfter completing this section, you should be able to explain why the addition of H2<\/sub>O to a chiral alkene leads to unequal amounts of diastereomeric products.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n
\r\n
\r\n
\r\n
\r\n

Study Notes<\/h3>\r\nIn the previous section, the addition of water to the achiral alkene produced a racemic mixture of two enantiomeric alcohols. They are produced in equal amounts so the mixture is optically inactive. What would occur if we carried out a similar reaction on a chiral alkene? Consider (S<\/em>)-3-methyl-1-pentene reacting with water (acid catalyzed). Proton addition produces a carbocation intermediate that is chiral (*\u00a0denotes stereogenic centre). That intermediate does not have a plane of symmetry and therefore attack by water is not equal from the top and bottom. This ultimately produces R<\/em> and S<\/em> products in a non 50:50 ratio.\r\n\r\n\"alkene\r\n\r\n<\/div>\r\n<\/div>\r\n
\r\n
\r\n
\r\n

Exercises<\/h3>\r\n
\r\n
\r\n

Question<\/h4>\r\n1.<\/b>\r\n\r\nPredict the products of the following reaction showing stereochemistry.\r\n\r\n\"\"\r\n\r\n<\/div>\r\n
\r\n

Solution<\/h3>\r\n1.\r\n[reveal-answer q=\"990518\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"990518\"]<\/b>\r\n\r\n\"\"\r\n\r\nThe products are diastereomers of one another[\/hidden-answer]<\/b>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n
<\/div>\r\n<\/div>\r\n<\/div>\r\n
\r\n

Contributors<\/h3>\r\n