Organic Reactions: Esters, Carboxylic Acids, and Acid Chlorides

Flashcards covering reactions, conditions, and specific observations for esters, carboxylic acids, and acid chlorides based on lecture notes.

Acid hydrolysis of Ester

A reaction using $dilute\,HCl$ or $dilute\,H_2SO_4$ with heat to convert an ester into a carboxylic acid and an alcohol.

Alkaline hydrolysis of Ester

A reaction involving $NaOH(aq)$ or $KOH(aq)$ and heat that produces a carboxylate salt ($CH_3-C-O^-$) and an alcohol.

Reduction of Esters or Carboxylic Acids

A process using the reducing agent $LiAlH_4$ to produce alcohols (e.g., $CH_3CH_2OH$).

Redox reaction of Carboxylic Acid with $Na(s)$

A reaction that produces a carboxylate salt ($CH_3-C-ONa$) and $H_2(g)$, characterized by the observation of effervescence of hydrogen gas.

Acid-base reaction of Carboxylic Acid with $Na_2CO_3(s)/(aq)$

A reaction resulting in a carboxylate salt ($CH_3-C-ONa$), $H_2O$, and $CO_2(g)$, characterized by the observation of effervescence of carbon dioxide gas.

Nucleophilic (acyl) substitution with anhydrous $PCl_5$

A reaction with a carboxylic acid that forms an acid chloride ($CH_3-C-Cl$), producing misty, white fumes of $HCl$.

Oxidation to form Carboxylic Acid

The conversion of alcohols or aldehydes using $K_2Cr_2O_7$ or $KMnO_4$ and $dilute\,H_2SO_4$ under heat (reflux).

Esterification (Carboxylic Acid)

Nucleophilic (acyl) substitution of a carboxylic acid with an alcohol (e.g., $CH_3CH_2OH$) using $conc.\,H_2SO_4$ catalyst and heat.

Hydrolysis of Acid Chloride

A nucleophilic (acyl) substitution reaction with $H_2O$ at room temperature ($r.t.$) to form a carboxylic acid ($CH_3-C-OH$).

Ester formation from Acid Chloride

A reaction with an alcohol at room temperature ($r.t.$) to form an ester; unlike carboxylic acids, this method does not require heat or concentrated acid catalysts.

Reaction of Acid Chloride with Phenol

A reaction that forms an ester only in the presence of a trace of $NaOH$.

Amide formation from Acid Chloride

The reaction of an acyl chloride with $NH_3$ or an amine (e.g., $CH_3CH_2NH_2$) at room temperature ($r.t.$) to produce an amide.

Carboxylic Acid and Amine at room temperature

An acid-base reaction occurs instead of amide formation, generating an alkyl ammonium carboxylate salt ($RNH_3^+ RCOO^-$).

Reactivity of Acyl Chlorides

Highly reactive due to two highly electronegative atoms ($Cl$ and $O$) making the carbon atom of the acyl group extremely electron deficient and susceptible to nucleophilic attack.