Deck 15: Carboxylic Acids and Nitriles

Question 1

Draw structures corresponding to each of the following IUPAC names.
Draw:
2-propylpentanoic acid

Answer 1

Question 2

Draw structures corresponding to each of the following IUPAC names.
Draw:
cis-cyclopentane-1,3-dicarboxylic acid

Answer 2

Question 3

Consider the data in the table below to answer the following question(s).
I
Refer to instructions. Explain why cyanoacetic acid and methoxyacetic acid are more acidic than their correspondingly substituted benzoic acid counterparts.

Answer 3

Electron-withdrawing groups, like −CN and −OCH₃, inductively withdraw electron density, which stabilizes the resulting carboxylate anion and thus increases the acidity of the carboxylic acid. These inductive effects are strongly dependent on distance. The −CN and −OCH₃ substituents are closer to the carboxylate in the substituted acetic acids than in the substituted benzoic acids, so their effect is greater.

Question 4

Consider the data in the table below to answer the following question(s).
I
Refer to instructions. Calculate the percent dissociation of 0.100 M solution of m-methoxybenzoic acid.

Question 5

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 6

Consider the data in the table below to answer the following question(s).
I
Refer to instructions. Which of the acids in the table has the strongest conjugate base?

Question 7

At pH 3.80 calculate the % in the dissociated and undissociated form in a 0.00200 M solution of pyruvic acid, pK_a = 2.39.

Question 8

Draw structures corresponding to each of the following IUPAC names.
Draw:
cyanoacetic acid

Question 9

Draw structures corresponding to each of the following IUPAC names.
Draw:
2-chlorobenzoic acid

Question 10

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 instructions. This reaction can be described as a _____ process.

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

Question 11

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 12

Draw structures corresponding to each of the following IUPAC names.
Draw:
prop-2-enenitrile

Question 13

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.
What is the order of increasing reactivity for the following compounds in electrophillic aromatic substitution reactions? (least to most reactive) ​
PK_a

A) IV, I, II, III
B) III, II, I, IV
C) II, III, I, IV
D) III, II, i, IV

Question 14

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 15

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 instructions. Write the complete reaction sequence for the process described above.

Question 16

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.
What is the order of increasing acidity for the following compounds? (least to most)

A) IV, I, III, II
B) IV, II, III, I
C) II, III, I, IV
D) I, III, II, IV

Question 17

An ether solution contains the following components.
2,3,4,5-tetramethylbenzene benzyl alcohol 2-hydroxybenzoic acid
If this solution is extracted with a 5% solution of NaHCO₃, that is immiscible with ether, which components end up in the ether layer and which in the NaHCO₃ layer?

Question 18

Consider the data in the table below to answer the following question(s).
I
Refer to instructions. Draw the structure of the strongest acid in the table.

Question 19

Draw structures corresponding to each of the following IUPAC names.
Draw:
phenylacetonitrile or phenylethanenitrile

Question 20

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 21

What is the major organic product obtained from the following reaction?

A)

B)

C)

D)

Question 22

Which of the following would represent the correct reaction conditions for the following conversion?

A) 1) KMnO₄, 2) LiAlH₄
B) 1) Mg, ether, 2) CO₂, 3) LiAlH₄
C) 1) NaOH, H₂O, 2) LiAlH₄
D) 1) SOCl₂, benzene, 2) LiAlH₄
E) either b or c

Question 23

Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain.
Complete the following reaction sequence with the missing major organic products.

Question 24

What is the major organic product obtained from the following reaction?

A)

B)

C)

D)

Question 25

The product shown can be synthesized by two different pathways as shown by the reaction conditions. Draw the structure of starting materials that should be placed in each of the boxes.

Question 26

What is the major organic product obtained from the following reaction?

A)

B)

C)

D)

Question 27

Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

A) FCH₂COOH > CH₃COOH > F₂CHCOOH
B) FCH₂COOH > CH₃COOH > CH₃OH
C) CH₃CH₂OH > ClCH₂COOH > BrCH₂COOH
D) CH₃COOH > ClCH₂COOH > CH₃OH

Question 28

What is the IUPAC name of the following compound?

A) 5,5-dimethyl-5-phenylpentanoic acid
B) 5-methyl-5-phenylhexanoic acid
C) 2,2-dimethylphenylpropanoic acid
D) 5,5-dimethyl-5-phenylbutanal

Question 29

Which of the following has the highest boiling point?

A) butanoic acid
B) butan-2-ol
C) hexanoic acid
D) heptan-3-one

Question 30

Consider the following ¹H NMR to answer the following question.
Refer to instructions. This compound is known to contain both a −C=O group and an −OH group. Based on this spectrum, this compound would be classified as:

A) aromatic carboxylic acid
B) aliphatic carboxylic acid
C) carbonyl containing an alcohol functional group
D) either a or b

Question 31

Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain.
Choose best method:

Question 32

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Refer to instructions and answer the following questions.
a)Give major product(s): b)Draw the structure of the intermediate product(s) that form(s).

Question 33

Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain.
Choose best method:

Question 34

Draw the structure of (Z)-4-methylhex-3-enoic acid.

Question 35

Which of the following does not represent a similarity between nitriles and carboxylic acids?

A) contain 3 carbon bonds to an electronegative element
B) contain two π bonds.
C) act as electrophiles
D) undergo nucleophilic substitution reactions
E) all of these are characteristic of both nitriles and carboxylic acids.

Question 36

Based on the following IR spectrum, this compound would be classified as:

A) aliphatic carboxylic acid
B) aromatic carboxylic acid
C) aliphatic nitrile
D) aromatic nitrile
E) carbonyl containing an alcohol functional group