Deck 20: Carboxylic Acids and Nitriles

Question 1

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.

Answer 1

Question 2

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Answer 2

2-hydroxybenzoic acid

Question 3

Draw: m-chlorobenzoic acid

Answer 3

Question 4

Draw: 2-propenenitrile

Question 5

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Question 6

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Question 7

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Question 8

Even though the para position is one carbon farther from the carboxy group than the meta position,p-cyanobenzoic acid is more acidic than m-cyanobenzoic acid.Explain the differences in acidity between p-cyanobenzoic acid and m-cyanobenzoic acid.

Question 9

What is the correct name for the following structure?

A)2-oxohexanoic acid
B)5-oxohexanoic acid
C)methyl butroxoketone
D)4-ketopentanoic acid

Question 10

Name the following substance.Atoms other than carbon and hydrogen are labeled.

Question 11

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.

Question 12

Explain the differences in acidity between p-methoxybenzoic acid and m-methoxybenzoic acid.

Question 13

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?

Question 14

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Question 15

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Question 16

Draw: 2-propylpentanoic acid

Question 17

Draw: cis-1,3-cyclopentanedicarboxylic acid

Question 18

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.

A)carbonylation
B)carboxylation
C)carbaniolation
D)cationation

Question 19

Name the following substance.Atoms other than carbon and hydrogen are labeled.

Question 20

Draw: cyanoacetic acid

Question 21

In order to produce a carboxylic acid as a product of the Grignard reaction,the Grignard reagent reacts with:

A)CO₂
B)a methyl ketone
C)a methyl ester
D)an aldehyde
E)either or CO₂ a methyl ketone

Question 22

Which of the following is not an acyl derivative of a carboxylic acid?

A)nitrile
B)ester
C)amide
D)acid chloride

Question 23

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

Question 24

In a solution of acetic acid ( ) at physiological pH of 7.3,it is most accurate to represent this substance as:

A)CH₃CO₂H
B)CH₃CO₂^-
C)CH₃CO₂H and CH₃CO₂^-

Question 25

​Draw the mechanism for the preparation of nitriles by dehydration of a primary amide, e.g. ,propanamide,using thionyl chloride.

Question 26

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

A)3.83
B)6.06
C)4.18
D)3.48

Question 27

Which labeled peaks would disappear if D₂O were added to the sample?

A)1
B)2
C)3
D)4
E)All peaks would disappear.

Question 28

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?

A)(¹H NMR)
B)(¹³C NMR)
C)DEPT-90
D)DEPT-135
E)All would distinguish between the two isomers.

Question 29

​Draw the mechanism of the conversion of isopropyl nitrile to an amine.

Question 30

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.

Question 31

Which of the following is not a common feature of both carboxylic acids and nitriles?

A)carbon atom with three bonds to an electronegative atom
B)presence of π bonds
C)can act as electrophiles
D)occur frequently in living organisms
E)All characterize both functional group classes.

Question 32

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.