Question 1

Which of the following statements best explains why carboxylic acids have higher boiling points than alcohols of similar molecular weight?

Accepted Answer

Carboxylic acids can form two hydrogen bonds per molecule, leading to dimer formation.

Question 2

What is the correct IUPAC name for the compound with the structure $$\mathrm{CH_3CH_2CH_2CN}$$?

Accepted Answer

Butanenitrile

Question 3

Which method would NOT synthesize a carboxylic acid from an alkyl benzene?

Accepted Answer

Reduction with $$\mathrm{$$LiAlH_4$$}$$

Question 4

Which of the following bases can deprotonate acetic acid ($$pK_a = 4.8$$)?

Accepted Answer

Water ($$pK_a = 15.7)$$

Question 5

Which structural feature makes the conjugate base of acetic acid more stable than that of phenol?

Accepted Answer

The conjugate base of acetic acid has two resonance structures that delocalize the negative charge over two oxygen atoms.

Question 6

Which of the following would increase the acidity of a carboxylic acid?

Accepted Answer

Adding an electron-withdrawing group closer to the carboxy group.

Question 7

What is the correct name for the salt formed when propanoic acid reacts with potassium hydroxide?

Accepted Answer

Potassium propanoate

Question 8

Which of the following is the correct formula for calculating the isoelectric point ($$pI) of an $$amino acid?

Accepted Answer

$$pI = \frac{pK_a(\mathrm{COOH}) + pK_a(\mathrm{NH_3$^+})}{2}$$

Question 9

Which of the following statements about the physical properties of carboxylic acids is TRUE?

Accepted Answer

Carboxylic acids can hydrogen bond with water, increasing their solubility.

Question 10

Which of the following compounds is responsible for the sting of some ants?

Accepted Answer

Formic acid

Question 11

Which of the following reactions is used to prepare nitriles from alkyl halides?

Accepted Answer

SN2 substitution with $$\mathrm{CN^-}$$

Question 12

Which IR absorption is characteristic of the C=O group in carboxylic acids?

Accepted Answer

$$\sim 1710\ \mathrm{cm}^{-1}$$

Question 13

Which of the following statements about amino acids is FALSE?

Accepted Answer

Amino acids are uncharged neutral molecules in water.

Question 14

Which of the following is the correct product when a nitrile is hydrolyzed in acidic conditions?

Accepted Answer

A carboxylic acid

Question 15

Which of the following best describes the hybridization and geometry of the carbon atom in the cyano group ($$\mathrm{C\equiv N}) of a $$nitrile?

Accepted Answer

sp hybridized, linear

Question 16

Which of the following would make benzoic acid more acidic?

Accepted Answer

Adding a nitro group to the ring

Question 17

Which of the following is the correct NMR chemical shift range for the O—H proton in carboxylic acids?

Accepted Answer

$$10-12\ \mathrm{ppm}$$

Question 18

Which of the following is the correct name for the compound with two carboxy groups on a three-carbon chain?

Accepted Answer

Malonic acid

Question 19

Which of the following is a common use for sodium benzoate?

Accepted Answer

As a fungal growth inhibitor and preservative in soft drinks

Carboxylic Acids and Nitriles (Chapter 19)

Study Guide - Practice Questions