Question

Orgo II Tutorial: Introduction to Carboxylic Acid Derivatives

Answer 1

\({\bf{Physical~Properties:}}\) of carboxylic acids
- high BP's and water solubility due to presence of C=O bond
- pkas in the 4-5 region
- acid strength increases w/ charge delocalization, often through the presence of electron withdrawing groups (note: this is an inductive not a resonance effect)

\({\bf{List~of~Derivatives:}}\) will be going in detail into the physical properties, synthesis, and reactions of these derivatives, but for now, know what they are

I would also add dicarboxylic acids (acids with two COOH groups instead of 1) and nitriles (componds with the CN triple bond)

Answer 2

\({\bf{Preparation~of~Carboxylic~Acids:}}\)
- oxidation of alkenes
> oxidation through KMnO4, OH-, heat mechanism OR through ozonolysis
in both of these methods the double bond is cleaved and an O is added to either end of the cleaved DB





- oxidation of aldehyde (Tollen's): Ag2O + THF/H2O will convert aldehyde to carboxylic acid
- oxidation of primary alcohol: jones oxidation (Cr reagent)

Answer 3

- hydrolysis of cyanohydrin (addition of HCN to a ketone followed up by acid)
> CN can also be added to alkyl halide to create a carboxylic acid via the same intermediate; extends the alkyl halide by 1 carbon

R-X + CN --> RCN --> add acid --> RCOOH



- grignards: create the grignard reagent, then adding CO2 with H3O+ will create R-COOH. note that the usual limitations on grignards still apply, so be on the watch for incompatible groups.

Answer 4

\({\bf{Acyl~Addition~Mechanism~and~Reactivity:}}\)


Reactivity: based on LG ability
acyl halides > anhydrides > esters > amines

generally, it is easier to synthesis a less reactive compound from a more reactive compound, rather than the other way around

Answer 5

Anyway, that's the end of my tutorial, I hope it was a helpful resource. Source material is Organic Chemistry 12th edition by Solomons, et. al.