Synthesis of 1-bromopentane Lab Worksheet Introduction/Summary This experiment utilizes SN2 chemistry to convert 1-pentanol (n-pentanol) to...
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Synthesis of 1-bromopentane Lab Worksheet Introduction/Summary This experiment utilizes SN2 chemistry to convert 1-pentanol (n-pentanol) to 1-bromopentane (n-bromopentane). The nucleophile for the reaction is bromide (Br-). The nucleophile in this lab is generated from an aqueous solution of sodium bromide. The sulfuric acid acts as a catalyst in converting the -OH functional group of pentanol to a better leaving group (water). The by-products for this lab are 1-pentene, di-n-pentyl ether, and the starting alcohol (n- pentanol). By-products can be removed by extraction using concentrated sulfuric acid. The product can then be removed from sulfuric acid, since it does not mix with H2SO, and will remain as a separate layer. H .SO OH Na Br Procedure (thanks to NileRed) Watch the following video using this link: https://www.youtube.com/watch?v=Y4bC_buRAmk Questions - Please neatly handwrite your answers to the follow questions. (You do not need to re-write the questions, just number your answers accordingly!) 1. Show the FULL mechanism for the conversion of 1-pentanol to 1-bromopentane, include the name of the mechanism ( i.e. E1 or E2, Sn1 or Sn2). 2. Look up and write down the following physical properties: a. density, MW, BP of 1-pentanol b. density, MW, and BP of 1-bromopentane 3. To illustrate how the by-products (1-pentene and di-n-pentyl ether) form, show the full mechanism for the formation of both, include the name of the mechanism. 4. In this reaction, HBr is made "in situ" - what does "in situ" mean? 5. What is meant by "reflux"? What key pieces of laboratory glassware are needed to perform a reflux? 6. After refluxing and allowing the reaction mixture to cool, why is the upper layer the 1-bromopentane product? 7. Around the 8-minute mark, NileRed mentions the "work up" of the reaction that he will eventually do. What is meant by "work up" ? 8. During the work-up, how does sulfuric acid get rid of any unreacted 1-pentanol starting material? 9. Why does the organic layer appear "cloudy" when water is present? 10. Show the calculations for the theoretical yield and %-yield for this reaction.

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