Carbonyl Compounds 2

Chloride is a good leaving group making the molecule very reactive. This reactivity makes it unsuitable to be used directly as a pharmaceutical drug, but it is useful for synthesizing many different drug molecules.

The reaction of acid chlorides with water results in the formation of carboxylic acids. This reaction is called hydrolysis.

When acid chlorides react with alcohols in the presence of a base, esters are formed.

The reaction of acid chlorides with amines in the presence of a base leads to the formation of secondary amides.

Acid chlorides can be synthesized by reacting a carboxylic acid with thionyl chloride (SOCl2). This reaction replaces the OH group of the carboxylic acid with a chlorine atom.

The reaction of acid chlorides with ammonia (NH3) to produce primary (RNH2) and secondary (R2NH) amines. This reaction is used to synthesize amides.

A reagent that is used to neutralize hydrochloric acid (HCl) during amide synthesis. It can be an amine like triethylamine or pyridine, or a strong base like sodium hydroxide (NaOH).

A type of reaction that replaces a hydroxyl group (-OH) with a chlorine atom (-Cl). It's often used to convert carboxylic acids to acid chlorides.

The process of reducing a nitro group (-NO2) to an amine group (-NH2). This is a key step in the synthesis of procaine, a local anesthetic.

A reagent used in the reduction of nitro groups to amines. It is a form of finely divided nickel that is used as a catalyst in hydrogenation reactions.

A common reaction mechanism used in synthetic chemistry, involving the step-by-step addition of a nucleophile to a carbonyl group.

A local anesthetic used to numb areas of the body. It is synthesized through a series of reactions involving chloroacetyl chloride and diethylamine.

An intermediate compound used in the synthesis of lidocaine. It is formed by the reaction of chloroacetyl chloride with diethylamine.

The carbonyl group (C=O) undergoes nucleophilic addition reactions where a nucleophile attacks the electrophilic carbonyl carbon.

The carbonyl group's carbon changes from sp2 hybridized to sp3 hybridized, resulting in a tetrahedral alkoxide ion intermediate.

Aldehydes generally react faster than ketones in nucleophilic addition reactions. This is due to lower steric hindrance and increased electrophilicity of the carbonyl carbon in aldehydes.

Cyanide anion (CN-) adds to the carbonyl carbon to form a cyanohydrin. The reaction involves a nucleophilic addition followed by a protonation step.

The process of reducing an aldehyde or ketone involves adding a hydride ion (H-) to the carbonyl carbon.

Alkyl groups attached to the carbonyl carbon donate electron density, decreasing the positive charge on the carbonyl carbon and making it less electrophilic.

The nucleophile can approach the carbonyl carbon from above or below the plane of the molecule, creating a chiral center when all four atoms attached to the carbon are different.

Good nucleophiles are those that readily donate electron pairs to the electrophilic carbonyl carbon. Examples include hydride, alkynyl anions, and alkoxides.

A reaction where a hydride ion (H-) is transferred from a reducing agent to a carbonyl group, converting it to an alcohol.

A common reducing agent for carbonyl compounds, often used in organic chemistry. It contains a boron atom with four hydride ions.

Another powerful reducing agent for carbonyl compounds, containing aluminum with four hydride ions. It's more reactive than sodium borohydride.

The product formed when an aldehyde is reduced using a hydride reducing agent like NaBH4 or LiAlH4.

The product formed when a ketone is reduced using a hydride reducing agent like NaBH4 or LiAlH4.

The process where an aldehyde is converted to a carboxylic acid by losing a hydrogen atom. It can be done chemically using oxidizing agents.

A reaction involving the addition of an alcohol to a carbonyl group, leading to the formation of hemiacetals and acetals.

A type of cyclic sugar formed from the intramolecular reaction of D-glucose, with two different anomeric forms: alpha and beta.

Two sugars that differ only in the configuration of the carbon that was the carbonyl group in the open-chain form.

The molecule NADH (nicotinamide adenine dinucleotide) plays a crucial role in biological reduction reactions by donating hydride ions.

The -OH group at C-1 in glucose can be oriented either above or below the plane of the ring, resulting in two structural forms.

Glucose can form rings of different sizes, but the six-membered pyranose ring is the most common.

Acyl substitution reactions involve the replacement of a group attached to a carbonyl carbon by a nucleophile. It is a two-step process: nucleophilic addition to the carbonyl followed by elimination of the leaving group.

Carboxylic acid derivatives react by the same general mechanism, but the reactivity varies depending on how easily the leaving group departs. More basic leaving groups are harder to remove, so the compound is less reactive.

Inductive effects refer to the electron-withdrawing abilities of atoms or groups that influence the electron density at the carbonyl carbon. More electronegative groups withdraw electrons, making the carbonyl carbon more electrophilic and reactive.

Orbital overlap, especially resonance structures, influences the stability and reactivity of carboxylic acid derivatives. More effective overlap leads to greater stability and lower reactivity.

To activate carboxylic acids for reactions, they are often converted into acid halides or anhydrides, which are more reactive due to better leaving groups.

The reaction mechanism of nucleophilic acyl substitution involves a tetrahedral intermediate formed by addition of a nucleophile to the carbonyl carbon. Elimination of the leaving group from this intermediate regenerates the carbonyl group and leads to the substitution product.

The reactivity of carboxylic acid derivatives can be explained by considering the leaving group ability and the electron-withdrawing effects of the substituents. More basic leaving groups are harder to remove, making the compound less reactive.

Amides are the least reactive carboxylic acid derivatives due to strong resonance stabilization. The nitrogen lone pair participates in resonance, resulting in a stable electron-delocalized structure.