Question 1

Which of the following statements best explains why carboxylic acids are more acidic than alcohols?

Accepted Answer

The carboxylate ion is stabilized by resonance, distributing the negative charge over two oxygen atoms.

Question 2

Which of the following carboxylic acids is expected to be the most acidic based on the substituent effects shown in the provided data?

Accepted Answer

$$\mathrm{Cl_3CCO_2H}$$

Question 3

What is the correct IUPAC name for the following compound: $$\mathrm{HOOC{-}CH_2${-}CH_2${-}COOH}$$?

Accepted Answer

Succinic acid

Question 4

Which reagent would you use to selectively reduce a carboxylic acid in the presence of an ester?

Accepted Answer

$$\mathrm{BH_3$}$$

Question 5

A student wants to synthesize butanoic acid from 1-bromopropane. Which sequence of reactions would achieve this transformation?

Accepted Answer

1. $$\mathrm{NaCN}$$, 2. $$\mathrm{H_3O^+}$$

Question 6

Which of the following best describes the effect of an electron-withdrawing group (such as $$\mathrm{NO_2$}) on $$the acidity of benzoic acid?

Accepted Answer

It increases the acidity by stabilizing the carboxylate ion.

Question 7

Given the following equilibrium: $$\mathrm{RCO_2H + H_2O \rightleftharpoons $$RCO_2$$^- + H_3O^+}$$, which expression correctly represents the acid dissociation constant $$K_a$$?

Accepted Answer

$$K_a = \frac{[$$RCO_2$$^-][H_3O^+]}{[RCO_2H]}$$

Question 8

Which of the following methods would NOT result in a one-carbon extension of the carbon chain when preparing a carboxylic acid?

Accepted Answer

Oxidation of a primary alcohol

Question 9

Which of the following carboxylic acids is the least acidic based on the provided pKa values?

Accepted Answer

$$\mathrm{CH_3CO_2H}$$

Question 10

Which of the following is a correct statement about the solubility of carboxylic acids and their salts?

Accepted Answer

Carboxylate salts are generally more water-soluble than their corresponding carboxylic acids.

Question 11

Which of the following is the correct order of increasing acidity for the following acids: acetic acid, bromoacetic acid, and propanoic acid?

Accepted Answer

Propanoic acid \u003c Acetic acid \u003c Bromoacetic acid

Question 12

Which of the following is NOT a carboxylic acid derivative?

Accepted Answer

A nitrile

Question 13

Which of the following reagents can be used to oxidize a primary alcohol to a carboxylic acid?

Accepted Answer

$$\mathrm{$$CrO_3$$, H_2SO_4} ($$Jones reagent)

Question 14

Which of the following statements about the preparation of carboxylic acids from alkyl benzenes is correct?

Accepted Answer

The side chain must contain at least one benzylic hydrogen for oxidation to occur.

Question 15

Which of the following best explains why the acidity of carboxylic acids increases with the addition of more electronegative substituents?

Accepted Answer

Electronegative substituents stabilize the negative charge on the carboxylate ion through inductive effects.

Question 16

Which of the following is the correct formula for the pKa of a carboxylic acid?

Accepted Answer

$$pK_a = -\log K_a$$

Carboxylic Acids and Nitriles: Structure, Properties, Acidity, and Synthesis

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