Question 1

Which of the following reagents is most commonly used to selectively reduce esters to aldehydes in organic synthesis?

Accepted Answer

DIBAL-H

Question 2

What is the major product when cyclohexanone reacts with ethylene glycol in the presence of an acid catalyst?

Accepted Answer

A cyclic acetal

Question 3

Which of the following statements best explains why the pK\_a of acetic acid ($$CH\_3COOH) is $$lower than that of ethanol ($$CH\_3CH\_2OH$$)?

Accepted Answer

The carboxylate ion is stabilized by resonance

Question 4

A student attempts to protect a primary alcohol using TBDMS-Cl and imidazole. What is the purpose of this protection step in a multi-step synthesis?

Accepted Answer

To prevent the alcohol from reacting with other reagents

Question 5

Which of the following is the correct IUPAC name for the compound with the structure $$CH\_3CH\_2COOH$$?

Accepted Answer

Propanoic acid

Question 6

When a Grignard reagent ($$RMgBr) $$reacts with formaldehyde ($$HCHO$$), what is the major organic product after acidic workup?

Accepted Answer

A primary alcohol

Question 7

Which method is most suitable for the oxidation of a primary alcohol to a carboxylic acid?

Accepted Answer

KMnO\_4

Question 8

A chemist wants to separate a mixture of benzoic acid and benzyl alcohol. Which technique would be most effective?

Accepted Answer

Extraction using aqueous NaOH

Question 9

Which of the following best describes the mechanism of nucleophilic addition to an aldehyde?

Accepted Answer

The nucleophile attacks the carbonyl carbon, followed by protonation of the oxygen

Question 10

Which of the following is a correct statement about the effect of electron-withdrawing groups (EWGs) on the acidity of carboxylic acids?

Accepted Answer

EWGs increase the acidity by stabilizing the carboxylate ion

Question 11

A student is given a mixture of hexanoic acid and hexanol. Which spectroscopic technique would best distinguish between these two compounds?

Accepted Answer

IR spectroscopy, looking for a strong absorption near $$1700\ 	ext{cm}^{-1}$$

Question 12

Which of the following reactions is used to prepare carboxylic acids from primary alcohols?

Accepted Answer

Oxidation with KMnO\_4

Question 13

What is the expected product when benzaldehyde reacts with methylmagnesium bromide ($$CH\_3MgBr) $$followed by acidic workup?

Accepted Answer

1-Phenylethanol

Question 14

Which protecting group is commonly used for alcohols and can be removed by treatment with fluoride ion?

Accepted Answer

TBDMS group

Question 15

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

Accepted Answer

Propanoic acid \u003c Acetic acid \u003c Formic acid

Question 16

A chemist performs a retro-synthetic analysis of ethyl benzoate. Which starting materials would be required for its synthesis via Fischer esterification?

Accepted Answer

Benzoic acid and ethanol

Question 17

Which of the following is a key difference between the reactivity of aldehydes and ketones toward nucleophilic addition?

Accepted Answer

Aldehydes are more reactive due to less steric hindrance and greater electrophilicity

Question 18

Which reagent would you use to convert a carboxylic acid to its corresponding methyl ester?

Accepted Answer

Methanol and acid catalyst

Question 19

A student treats a ketone with NaBH\_4. What is the expected product?

Accepted Answer

An alcohol

Question 20

Which of the following best describes the effect of resonance on the stability of the carboxylate ion?

Accepted Answer

Resonance delocalizes the negative charge, increasing stability

Aldehydes, Ketones, and Carboxylic Acids: Mechanisms, Properties, and Reactions

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