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Organic Chemistry

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HCl is added to t-pentyl alcohol in a vial to synthesize t-pentyl chloride. t-pentyl chloride separates on top and the bottom layer is discarded. Sodium bicarbonate is then used to wash the crude t-pentyl chloride. What is the purpose of this wash and why would it be bad to wash with sodium hydroxide?

  • Organic Chemistry -

    The NaHCO3 wash is to remove the excess HCl that was added initially. Would washing with NaOH reform the alcohol?

  • Organic Chemistry -

    NaOH is a strong base, so it would likely act as a nucleophile and attack the halide making it undergo an elimination reaction, forming an undesired compound.

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