Imines and Acetals Mechanisms

Equilibrium Position

The state where the rate of the forward reaction equals the rate of the reverse reaction

NaBH3CN Reactivity

Less reactive due to the weaker hydride donor ability compared to NaBH4

Hemiacetals

Formed in acidic or basic conditions when carbonyls react with alcohols

Acetals Catalyst

Necessary due to weak nucleophilicity of alcohol and poor leaving group ability of OH-

Dean Stark Apparatus

Device used to remove water from a reaction mixture to favor acetal formation

Protecting Groups

Acetals used to prevent nucleophilic addition in carbonyls, removable by hydrolysis

Electrophilicity

Property of having a low energy LUMO to accept an electron pair

Sterics in Ketones

More hindered than aldehydes due to bulky R groups

Electron Density in Ketones

Higher at C, making them less electrophilic than aldehydes

Esters and Amides Electrophilicity

Reduced by resonance effects in the molecule

Prochiral Carbonyls

Non-symmetrical carbonyls that can be converted into chiral compounds

Hydrolysis of Esters

Decomposition by water, possible under acidic or basic conditions

Acyl Halides Reactivity

Determined by electronegativity and leaving group ability, leading to easy hydrolysis

Acid Anhydrides

Contain two carbonyl groups, highly reactive due to resonance stabilization

Electrophilic Carbon

Carbon atom in a molecule that accepts an electron pair during a reaction