Carboxylic acid derivatives

Introducing reactions of carboxylic acid derivatives.

Esterification of acetic acid with ethanol:

Steps:

1. Carbonyl group in acetic acid is protonated;
2. Hydroxyl group in ethanol attacks the protonated carbonyl;
3. Hydroxyl group in the intermediate is protonated, and subsequently eliminated as a water molecule;
4. Proton on carbonyl group dissociates, forming ethyl acetate.

Lithium aluminum hydride reacts with ethyl acetate:

Steps:

1. Hydride ion in lithium aluminum hydride adds to the carbonyl group in ester;
2. Tetrahedral intermediate eliminates an ethoxy anion to generate an aldehyde;
3. Hydride ion in lithium aluminum hydride adds to the carbonyl group in aldehyde;
4. rotonation of alcohol anion forms the final product.

Lithium aluminum hydride reacts with dimethylformamide:

Steps:

1. Hydride in lithium aluminum hydride adds to the carbonyl group in amide;
2. The formed intermediate binds to aluminum hydride, and then eliminates an aluminum-oxygen species to generate an iminium ion;
3. Hydride in aluminum-oxide species adds to the C=N of iminium ion to form the imine product.