Question

how can you remove sodium bisulfate during extraction for synthesis 1-bromobutane lab

how can you remove sodium bisulfate during extraction for synthesis 1-bromobutane lab

Homework Answers

Answer #1

Actually you don't need to remove perse. That compound is in one of the layer (the aqueous layer) and the organic, which contains the 1-bromobutane. However, let me put you the part of the extraction here once again:

An excess of sulfuric acid is used in the experiment to provide a strongly acidic medium for the protonation of the alcohol. Sulfuric acid, which is a dehydrating agent, also combines with the water that is formed as a product of the substitution reaction. A number of side reactions occur in this reaction. 1-Butanol can react with HSO4 - ions present in solution to yield a hydrogen sulfate ester (ROSO3H). This inorganic ester, in turn, can undergo elimination to yield 1-butene (a gas that is lost during the reflux and work-up) or substitution with 1-butanol to yield di-n-butyl ether (which must be removed during work-up). Another side reaction that occurs is oxidation of the 1 -butanol by either H2SO4 or Br+ (formed by oxidation of Brby H2SO4). At the end of the reaction, the mixture consists of two phases. The upper layer contains the desired 1-bromobutane plus organic by-products, and the lower layer contains the inorganic components. The work-up techniques in this experiment consist of four steps: (1) an initial steam distillation; (2) extraction ; (3) drying ; and (4) a final distillation to purify the product. In the steam distillation, the water and 1-bromobutane co-distil, leaving the inorganic compounds behind in the distillation residue. Unfortunately, di-n-butyl ether, butanoic acid, and unreacted 1 -butanol also co-distil with water and must be removed from the distillate by extraction. The first extraction, a water wash, removes some of the 1-butanol, which is slightly soluble in water. The second extraction is with cold, concentrated sulfuric acid. (If the acid is not cold, extensive charring of the organic material will occur.) Each of the two major impurities (1- butanol as di-n-butyl ether) and the minor impurity (butanoic acid) contains an oxygen atom. In strong acid, each of these compounds is protonated to yield a sulfuric acid-soluble salt. 1- Bromobutane does not form a salt with sulfuric acid; consequently, it remains in the separatory funnel as a separate layer. This extraction is thus an example of a chemically active extraction. A subsequent extraction with aqueous sodium hydroxide solution removes any sulfuric acid clinging to the sides of the separatory funnel. The wet alkyl halide is then dried with anhydrous calcium chloride. Calcium chloride is the drying agent of choice in this reaction because it forms complexes with any residual alcohol, as well as with water. After drying, the 1-bromobutane is purified by distillation.

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