Upon completing a synthetic procedure, every chemist is faced with the job of cleaning glassware. Because the compounds present may be dangerous in some way or have unpleasant properties, a little serious chemical thinking is often beneficial before “doing the dishes.” Suppose that you have just completed a synthesis of hexanoyl chloride, perhaps to carry out the reaction in Problem 34(b); first, however, you must clean the glassware contaminated with this acyl halide. Both hexanoyl chloride and hexanoic acid have terrible odors. 

(a) Would cleansing the glassware with soap and water be a good idea? Explain. 

(b) Suggest a more pleasant alternative, based on the chemistry of acyl halides and the physical properties (particularly the odors) of the various carboxylic acid derivatives. 

Data From problem 34 (b)

(b)

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THF CuLi + CI