Functional Group Chemistry - Carbonyls

A set of question and answer flashcards based on the lecture about functional group chemistry focusing on carbonyls, their properties, reactivity, and biological significance.

What are the three main types of compounds that contain carbonyl groups?

Carboxylic acids, aldehydes, and ketones.

What is the typical geometric structure of a carbonyl group (C=O)?

Trigonal planar, with sp2 hybridization of carbon and oxygen.

What role do carbonyl groups typically play in chemical reactions?

They act as electrophiles in nucleophilic addition reactions.

What is the hybridization of carbon in carbonyl compounds?

sp2 hybridized.

How do aldehydes compare to ketones in terms of reactivity?

Aldehydes are generally more reactive than ketones in nucleophilic addition reactions.

What is the effect of protonation on the reactivity of carbonyl compounds?

Protonation increases the electrophilicity of the carbonyl carbon, making it more susceptible to nucleophilic attack.

What is the acidity range (pKa) for typical carboxylic acids?

The pKa values for most aliphatic and aromatic carboxylic acids fall within the range of 3 to 5.

What kind of interactions do carbonyl groups typically participate in regarding drug molecules?

Hydrogen bonding and dipole-dipole interactions.

What is the mechanism for acyl substitutions in carboxylic acid derivatives?

Nucleophile adds to the carbonyl carbon, forms a tetrahedral intermediate, and then expels a leaving group. Nucleophilic substitution

How do alcohols compare to carboxylic acids in terms of acidity?

Carboxylic acids are stronger acids than alcohols because of resonance stabilization of the carboxylate anion.

What is the significance of the Bürgi-Dunitz angle in relation to carbonyl reactions?

It influences the steric crowding and approach of nucleophiles to the carbonyl carbon.

What is keto-enol tautomerization?

It is the interconversion between the keto form and the enol form of carbonyl compounds.

What determines the class of carboxylic acid derivatives?

The group bonded to the acyl carbon determines the class: -OH (carboxylic acid), -Cl (acid chloride), etc.

What are examples of biologically relevant carboxylic acid derivatives mentioned in the lecture?

Acetyl-coenzyme A, adenosine-5'-triphosphate (ATP).

What reaction leads to the formation of the carboxylate ion in carboxylic acids?

The transfer of a proton from the carboxylic acid to water. Deprotonation