MPharm Programme - PHA114 Carbonyl Compounds 1

<p>fraction of HA ionised = 1 + antilog10(pKa - pH) (D)</p> Signup and view all the answers

<p>99% (D)</p> Signup and view all the answers

<p>Nucleophilic addition reactions (B)</p> Signup and view all the answers

<p>C=O (C)</p> Signup and view all the answers

<p>120° (D)</p> Signup and view all the answers

<p>They can donate protons to water. (C)</p> Signup and view all the answers

<p>Carboxylate anions are resonantly stabilized. (D)</p> Signup and view all the answers

<p>Acetic acid (A)</p> Signup and view all the answers

<p>Ethers (D)</p> Signup and view all the answers

<p>It involves a hydrogen atom bonded to an electronegative atom. (D)</p> Signup and view all the answers

<p>C=O is shorter and stronger than C=C. (B)</p> Signup and view all the answers

<p>Acyl halide (C)</p> Signup and view all the answers

<p>Penicillin N (A)</p> Signup and view all the answers

<p>Hydrolysis (B)</p> Signup and view all the answers

<p>Lactone (C)</p> Signup and view all the answers

<p>Secondary amide (B)</p> Signup and view all the answers

<p>Increase the acidity (A)</p> Signup and view all the answers

<p>It decreases the carboxylate's willingness to lose H (C)</p> Signup and view all the answers

<p>pKa = 0.64 (D)</p> Signup and view all the answers

<p>The functional group attached to the acyl carbon (A)</p> Signup and view all the answers

<p>Acid chlorides (C)</p> Signup and view all the answers

<p>Esters (B)</p> Signup and view all the answers

<p>It increases the electrophilicity of the carbonyl carbon (B)</p> Signup and view all the answers

<p>Nucleophilic attack on carbonyls (A)</p> Signup and view all the answers

<p>Polar nature of the carbonyl group (C)</p> Signup and view all the answers

<p>They participate in nucleophilic carboxyl substitution reactions (D)</p> Signup and view all the answers

<p>Hydrolysis can occur under acidic or basic conditions (B)</p> Signup and view all the answers

<p>Increase in acidity (C)</p> Signup and view all the answers

<p>Hydrides (B)</p> Signup and view all the answers

The negatively charged form of a carboxylic acid, formed by the loss of a proton (H+). It has a characteristic resonance structure with a negative charge delocalized between the two oxygen atoms.

A measure of the acidity of a weak acid. It reflects the equilibrium constant of the dissociation of the acid into its conjugate base and a proton.

The pH at which a weak acid is 50% ionized, meaning half of the acid molecules are in their undissociated form (HA) and half are in their ionized form (A-).

The proportion of a weak acid that exists in its ionized form (A-) at a specific pH.

The dependence of the fraction ionized of a weak acid on the pH of the solution. As the pH increases (becomes more basic), the fraction ionized also increases as the acid loses its proton and becomes more deprotonated.

A functional group consisting of a carbon atom double bonded to an oxygen atom and single bonded to a hydrogen atom. Often found in aldehydes.

A functional group consisting of a carbon atom double bonded to an oxygen atom and single bonded to two carbon atoms.

A functional group consisting of a carbon atom double bonded to an oxygen atom and single bonded to a hydroxyl group. Often found in organic acids.

A functional group consisting of a carbon atom double bonded to an oxygen atom and single bonded to a halogen atom. Often found in acyl halides.

A functional group consisting of a carbon atom double bonded to an oxygen atom and single bonded to an oxygen atom that is also single bonded to a hydrocarbon group. Often found in esters.

A functional group consisting of a carbon atom double bonded to an oxygen atom and single bonded to another carbonyl group.

A cyclic ester. A functional group consisting of a carbon atom double bonded to an oxygen atom and single bonded to an oxygen atom that is also single bonded to the same carbon chain.

A functional group consisting of a carbon atom double bonded to an oxygen atom and single bonded to an amino group. Often found in amides.

A functional group consisting of a carbon atom double bonded to an oxygen atom and single bonded to a sulfur atom that is also single bonded to a hydrocarbon group. Often found in thioesters.

A functional group consisting of a carbon atom triple bonded to a nitrogen atom. Often found in nitriles.

A non-covalent interaction that occurs between a hydrogen atom bonded to an electronegative atom and a lone pair of electrons on another electronegative atom.

The ability of a molecule to donate a proton to another molecule.

A measure of the acidity of a molecule. The lower the Ka, the weaker the acid.

The stabilizing effect of resonance on the carboxylate anion, making it more stable and therefore making the carboxylic acid a stronger acid.

Electron-withdrawing groups (EWGs) increase the acidity of carboxylic acids by pulling electrons towards themselves, enhancing the resonance stabilization of the carboxylate anion.

Electron-donating groups (EDGs) decrease the acidity of carboxylic acids by pushing electrons towards the carboxyl group, reducing the resonance stabilization of the carboxylate anion.

Carboxylic acids, esters, amides, anhydrides, and acid chlorides are all derivatives of carboxylic acids, differing in the group attached to the acyl carbon.

The reactivity of carboxylic acid derivatives decreases in the following order: acid chloride > anhydride > ester > amide > carboxylate.

Carboxylic acid derivatives can be interconverted through nucleophilic acyl substitution reactions. All can be converted back to the parent carboxylic acid by acidic or basic hydrolysis.

The carbonyl group is polar due to the electronegativity difference between carbon and oxygen, making the carbonyl carbon electrophilic and susceptible to nucleophilic attack.

The reactivity of carbonyl compounds can be enhanced by protonation of the carbonyl oxygen, making the carbonyl carbon more electrophilic and prone to nucleophilic attack.

Strong nucleophiles can directly attack the carbonyl carbon without requiring activation. Weak nucleophiles require activation, often achieved through acid catalysis.

Nucleophilic addition reactions are reversible, with the direction of equilibrium dependent on factors like reaction conditions and relative stabilities of reactants and products.

Nucleophiles can be negatively charged or neutral species containing an electron-rich center that can donate electrons to the carbonyl carbon.

The Bürgi-Dunitz angle describes the preferred trajectory of a nucleophile attacking a carbonyl carbon. It is approximately 107 degrees.

Thioesters and acyl phosphates are important biological carboxylic acid derivatives, playing key roles in metabolism and energy transfer.

Acetyl coenzyme A (Acetyl-CoA) is a critical thioester derivative involved in many metabolic reactions, particularly in energy production.

ATP (adenosine triphosphate) is a crucial acyl phosphate derivative that serves as the primary energy currency in living organisms.

Nucleophilic carboxyl substitution reactions are common in biological systems and often involve enzymes that catalyze these transformations.