Q: Which of the following is a correct statement about the spectroscopy of carboxylic acids?

They show a broad O-H stretch around $$2500-3300\ \text{cm}^{-1} in IR $$spectra

Question 1

Which of the following is the correct IUPAC name for the compound with the structure $$CH_3CH_2OCH_2CH_3$$?

Accepted Answer

Diethyl ether

Question 2

Which reagent would you use to synthesize an ether via the Williamson ether synthesis from 1-bromopropane and sodium methoxide?

Accepted Answer

$$CH_3ONa$$

Question 3

What is the major organic product when diethyl ether is treated with excess concentrated hydrobromic acid ($$HBr$$)?

Accepted Answer

Ethanol and ethyl bromide

Question 4

Which of the following best describes the mechanism for the acid-catalyzed opening of an epoxide with methanol?

Accepted Answer

Methanol attacks the more substituted carbon after protonation of the epoxide oxygen

Question 5

Which of the following statements about the reactivity of aldehydes and ketones is correct?

Accepted Answer

Aldehydes are generally more reactive than ketones toward nucleophilic addition

Question 6

Which of the following is the correct sequence for the formation of an epoxide from an alkene using a peroxycarboxylic acid?

Accepted Answer

Alkene reacts with peroxycarboxylic acid to form an epoxide in a single step

Question 7

A student wants to convert benzyl alcohol to benzoic acid. Which reagent would be most effective for this transformation?

Accepted Answer

$$KMnO_4$$ with acidic workup

Question 8

Which of the following best describes the product of the reaction between acetone and hydrogen cyanide ($$HCN$$)?

Accepted Answer

A cyanohydrin

Question 9

Which of the following carboxylic acids is expected to have the lowest pKa value?

Accepted Answer

Trichloroacetic acid

Question 10

Which of the following statements about Fischer esterification is correct?

Accepted Answer

It is an equilibrium process that requires an acid catalyst

Question 11

Which of the following is the correct application of the Henderson-Hasselbalch equation for a carboxylic acid with $$pK_a = 4.8$$ and a solution pH of $$6.8$$?

Accepted Answer

$$\displaystyle \frac{[A^-]}{[HA]} = 100$$

Question 12

Which of the following is a correct statement about the Baeyer-Villiger oxidation?

Accepted Answer

It converts ketones to esters using a peroxyacid

Question 13

Which of the following is the correct product of the Wittig reaction between benzaldehyde and methyltriphenylphosphonium ylide?

Accepted Answer

Styrene ($$C_6H_5CH=CH_2$)

Question 14

Which of the following best describes the reduction of a carboxylic acid with $$LiAlH_4$$?

Accepted Answer

The carboxylic acid is reduced to a primary alcohol

Question 15

Which of the following is the correct order of boiling points for the following compounds: ethanol, acetic acid, and diethyl ether?

Accepted Answer

Acetic acid \u003e ethanol \u003e diethyl ether

Question 16

Which of the following is the correct IUPAC name for the cyclic ether commonly known as THF?

Accepted Answer

Tetrahydrofuran

Question 17

A chemist wants to synthesize a carboxylic acid by reacting an alkyl halide with cyanide ion followed by acidic hydrolysis. Which inorganic source is being used to introduce the carboxyl group?

Accepted Answer

$$CN^-$$

Question 18

Which of the following best describes the product of the acid-catalyzed hydration of formaldehyde?

Accepted Answer

A geminal diol

Question 19

Which of the following is a correct statement about the spectroscopy of carboxylic acids?

Accepted Answer

They show a broad O-H stretch around $$2500-3300\ 	ext{cm}^{-1} in IR $$spectra

Question 20

Which of the following is the correct mechanism for the formation of a cyclic acetal from a ketone and a diol under acidic conditions?

Accepted Answer

Nucleophilic attack by the diol, followed by proton transfers and loss of water

Study Guide: Ethers, Epoxides, Aldehydes, Ketones, and Carboxylic Acids

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