Exam 20: Carboxylic Acids and Nitriles

Draw the structure of the reactant needed to form the following upon treatment with SOCl₂ at a moderately elevated temperature.Atoms other than carbon and hydrogen are labeled.

A sample is known to contain either hexanoic acid or 3-methylpentanoic acid.Which of the following spectra would not distinguish between the two isomers?

Exhibit 20-2 Consider the data below to answer the following question(s). When CO₂ is bubbled through an ether solution of benzylmagnesium bromide,and the resulting mixture is acidified,phenylacetic acid is produced.Any unreacted benzylmagnesium bromide is converted to toluene in the acidification step. -Refer to Exhibit 20-2.Write the complete reaction sequence for the process described above.

Draw: cis-1,3-cyclopentanedicarboxylic acid

Propose a synthesis of the anti-inflammatory drug Ibuprofen from benzene.Show all reagents and all intermediate structures.Assume that ortho and para isomers can be separated.

Exhibit 20-2 Consider the data below to answer the following question(s). When CO₂ is bubbled through an ether solution of benzylmagnesium bromide,and the resulting mixture is acidified,phenylacetic acid is produced.Any unreacted benzylmagnesium bromide is converted to toluene in the acidification step. -Refer to Exhibit 20-2.This reaction is described as a _____ process.

​Draw the mechanism of the basic hydrolysis of methyl nitrile to yield methyl amide,which is then hydrolyzed to yield an acetate ion.

A solution of glycolic acid is prepared such that the glycolic acid is 69% dissociated.Calculate the pH of this solution.( )

Exhibit 20-2 Consider the data below to answer the following question(s). When CO₂ is bubbled through an ether solution of benzylmagnesium bromide,and the resulting mixture is acidified,phenylacetic acid is produced.Any unreacted benzylmagnesium bromide is converted to toluene in the acidification step. -Refer to Exhibit 20-2.How could you separate phenylacetic acid from toluene?

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Draw: m-chlorobenzoic acid

Draw the structure of the product formed when the following is treated with 1) NaOH (aq) and 2) H₃O⁺.Explain,if necessary how the product would be affected if the treatment with acid were omitted.