Chem 353-34

Chem 353-34 - 3 A student exposed R-1-bromo-2-propanol to...

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Post Lab Questions – Williamson Ether Synthesis (You may write the answers only in your notebook for the post lab questions if you choose.) 1. Write a mechanism for the cleavage of butyl isopropyl ether with HI at 100°C to form exclusively isopropyl alcohol and 1-iodobutane. Explain why butyl alcohol and isopropyl iodide are not formed in the reaction. 2. Crown ethers, like the one shown below, could potentially be substituted for the tetrabutylammonium bromide phase transfer catalyst used for this experiment. Explain how crown ether can also act as a phase transfer catalyst.
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Unformatted text preview: 3. A student exposed R-1-bromo-2-propanol to sodium hydroxide, isolated an optically active product, and collected the proton NMR below. What is the structure of the compound that the student isolated? 4. Which of the hydrogens from the answer to the question above are diastereotopic? 5. Another student performed the same reaction as in question #3, isolated an optically inactive product, and collected the proton NMR below. What is the structure of the compound that this student isolated?...
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This note was uploaded on 04/06/2011 for the course CHEM 353 taught by Professor Bronson during the Winter '11 term at BYU.

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