The order of addition of the bases is important. What would have happened if you instead treated the initial mixture of benzoic acid, 2 - napthol and 1,4-dimethoxybenzene with a 1M NaOH aqueous solution instead of the saturated NaHCO3 solution? How would the separation of the compounds be affected? What would change?

How do you construct a flow chart using extraction to separate a mixture of the 3 solids used below if dicholoromethane is the solvent and any other reagents can be used. The 3 solids are: pyrazole, p-chlorobenzoic acid, and benzophenone.

a) To a solution of 10 g (60 mmol) of 3-nitrophenylacetic acid in 120 ml of ethanol were added 20 ml of a saturated 5 solution of hydrogen chloride in ethyl acetate and the mixture was heated at reflux for 4 hours, cooled and left to stand at room temperature for 18 hours. The mixture was evaporated and the residue was partitioned between 120 ml of diethyl ether and 100 ml of saturated aqueous sodium 10 bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 10.3 g. (82%) of ethyl 3-nitrophenylacetate as a pale yellow oil. [NMR spectrum (250 MHz) 81.25(t) (3H), 83.68(s) (2H), 84.6(q) (2H), 86.5-86.7(m) (3H), 87.09(dd) (1H)].

6. Identify compound X in the scheme below. Ph LiAlH4 Et₂O then aqueous workup Dess-Martin or Ley or Swern or PDC compound X