QCM : Carbonyl Chemistry Masterclass — 9 questions

Questions et réponses du QCM

1. What is the carbonyl functional group characterized by?

A carbon atom single-bonded to two oxygen atoms
A carbon atom double-bonded to an oxygen atom (>C=O)
A carbon atom bonded to a nitrogen atom (C≡N)
A carbon atom bonded to a hydroxyl group (-OH)

A carbon atom double-bonded to an oxygen atom (>C=O)

Explication

The carbonyl functional group is characterized by a carbon atom double-bonded to an oxygen atom (>C=O), which is fundamental in aldehydes, ketones, and other related compounds.

2. Who developed the Gatterman-Koch reaction for synthesizing aromatic aldehydes?

Gatterman and Koch, 1904
Fischer and Baeyer, 1890
Rosenmund and Schmitt, 1920
Wittig and Zeeman, 1910

Gatterman and Koch, 1904

Explication

The Gatterman-Koch reaction, used for synthesizing aromatic aldehydes like benzaldehyde, was developed by Gatterman and Koch in 1904. This is a well-documented historical fact in organic chemistry.

3. What is the primary purpose of oxidizing primary alcohols with mild oxidants like PCC in preparation methods?

To dehydrate alcohols into alkenes
To synthesize ketones from secondary alcohols
To convert aldehydes into carboxylic acids efficiently
To produce aldehydes selectively without further oxidation to acids

To produce aldehydes selectively without further oxidation to acids

Explication

Oxidizing primary alcohols with mild oxidants like PCC is specifically used to produce aldehydes selectively, stopping oxidation at the aldehyde stage without further oxidation to acids. This controlled oxidation is essential for synthesizing aldehydes in laboratory and industrial settings.

4. Arrange the following aldehydes and ketones in order of increasing molecular size based on their physical states at room temperature.

Methanal as a solid, ethanal as a gas, higher aldehydes and ketones as liquids
Methanal as a gas, ethanal as a solid, higher aldehydes and ketones as liquids
Methanal as a gas, ethanal as a liquid, higher aldehydes and ketones as solids
Methanal as a liquid, ethanal as a solid, higher aldehydes and ketones as gases

Methanal as a gas, ethanal as a liquid, higher aldehydes and ketones as solids

Explication

Methanal (formaldehyde) is gaseous at room temperature due to its small size and low molecular weight. Ethanal (acetaldehyde) is a volatile liquid, and higher aldehydes and ketones have larger molecular weights, making them liquids or solids at room temperature. This sequence reflects the typical physical states of aldehydes and ketones as their molecular size increases.

5. How do aldehydes and ketones differ in their bonding and reactivity?

Ketones have a carbonyl group bonded to two hydrogen atoms, whereas aldehydes have it bonded to two alkyl groups.
Aldehydes have a carbonyl group bonded to a hydrogen, making them more reactive than ketones, which have two alkyl groups attached to the carbonyl carbon.
Aldehydes and ketones both have the same bonding structure but differ in their physical states at room temperature.
Aldehydes are less reactive than ketones because they have more alkyl groups attached to the carbonyl carbon.

Aldehydes have a carbonyl group bonded to a hydrogen, making them more reactive than ketones, which have two alkyl groups attached to the carbonyl carbon.

Explication

Aldehydes have a carbonyl group bonded to a hydrogen atom and a carbon chain, which makes them more electrophilic and generally more reactive than ketones, which have two alkyl groups attached to the carbonyl carbon, providing steric hindrance and electron donation that reduce reactivity.

6. Who proposed the Gatterman-Koch reaction for synthesizing aromatic aldehydes?

Gatterman and Koch
August Kekulé
Robert Burns Woodward
Louis Pasteur

Gatterman and Koch

Explication

The Gatterman-Koch reaction was proposed by Gatterman and Koch in 1904 as a method to synthesize aromatic aldehydes, especially benzaldehyde, from benzene derivatives using carbon monoxide and hydrogen chloride in the presence of catalysts.

7. How does the resonance stabilization of the conjugate base influence the acidity of carboxylic acids?

It increases acidity by stabilizing the conjugate base.
It has no effect on acidity, which is determined solely by the strength of the O-H bond.
It decreases acidity by destabilizing the conjugate base.
It decreases acidity by making the conjugate base less likely to accept protons.

It increases acidity by stabilizing the conjugate base.

Explication

Resonance stabilization of the conjugate base disperses the negative charge over two oxygen atoms, making the conjugate base more stable and thus increasing the acidity of the carboxylic acid.

8. Which reagent would you use in the laboratory to selectively oxidize a primary alcohol to an aldehyde without further oxidation to a carboxylic acid?

Pyridinium chlorochromate (PCC)
Potassium permanganate (KMnO₄)
Potassium dichromate (K₂Cr₂O₇)
Sodium borohydride (NaBH₄)

Pyridinium chlorochromate (PCC)

Explication

PCC is a mild oxidizing agent that selectively oxidizes primary alcohols to aldehydes without further oxidation to acids. Potassium dichromate and potassium permanganate are stronger oxidants that tend to oxidize aldehydes further to carboxylic acids. Sodium borohydride is a reducing agent, not an oxidant, so it would not oxidize alcohols.

9. What is the key structural component responsible for the chemical reactivity of aldehydes and ketones in industrial applications?

Amino group (-NH₂)
Carbonyl group (>C=O)
Hydroxyl group (-OH)
Ether linkage (-O-)

Carbonyl group (>C=O)

Explication

The carbonyl group (>C=O) is the key structural component in aldehydes and ketones that determines their reactivity and makes them useful in various industrial applications. Its polarity and resonance stabilization influence their chemical behavior, enabling reactions such as nucleophilic addition.

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Carbonyl group — structure?

C=O double bond, sp2 hybridized carbon.

Aldehydes — nomenclature?

Named with -al suffix, chain numbered from aldehyde carbon.

Ketones — nomenclature?

Named with -one suffix, numbered from nearest carbonyl.

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