Organic Lab Reactions 73

Organic Lab Reactions 73 - 68 ALIPHATIC FLUORINE COMPOUNDS...

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68 ALIPHATIC FLUORINE COMPOUNDS to oleyl alcohol to give a fluorostearyl alcohol of unknown structure. It adds to ketene to form acetyl fluoride, and to cyanic acid in ether solu- tion cooled to — 78° to form carbamyl fluoride, FCONH 2 . 49 Unpublished observations indicate that hydrogen fluoride adds with difficulty to CH 3 CH=CBr 2 , more readily to CH 3 CH=«CC1 2 , and rapidly and quan- titatively to CH 3 CH=CC1F and CH 3 CH=CF 2 . In all cases, a 1,1,1- trihalopropane results exclusively. 6 " A mixture of CH 2 =CC1CH 2 C1 and hydrogen fluoride forms CH 3 CC1FCH 2 C1. 60 The operation consists merely in mixing the re- agents at low temperature in a steel container, sealing, letting stand overnight at room temperature, cooling, pouring onto cracked ice, washing, and distilling. A conversion of about 50% is observed, and the balance of the chloroolefin is recovered. If the operation is altered by keeping the container overnight at 40°, the reaction proceeds to completion, and if excess hydrogen fluoride is present CH3CF2CH2CI
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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