A chemist attempted the synthesis of (R)-2-fluoropentane from (S)-2-pentanol. Un

Question

A chemist attempted the synthesis of (R)-2-fluoropentane from (S)-2-pentanol. Unfortunately, the chemist was not very successful and did not observe the desired product. Of the suggestions below, which is the best suggestion for producing the desired product in the highest yield? A) Change the solvent from CH3OH to (CH3)2S0 (DMSO) and change the starting material from a secondary alcohol to a primary alkyl halide. B) Change the solvent from CH3OH to (CH3)2S0 (DMSO) and change the starting material from (S)-2-pentanol to (S)-2-bromopentane. C) Change the solvent to H2O and make the substrate a tertiary alkyl halide. D) Change only the solvent from CH3OH to (0-13)2S0 (DMSO). E) Change only the starting material from (S)-2-pentanol to (S)-2-bromopentane. Which of the following compounds gives a single E2 product on reaction with sodium ethoxide, NaOCH2CH3?

Explanation / Answer

b) change the solvent from methanol to DMSO and change the starting material from (S)-2-pentanol to (S)-2-bromo pentane.

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