Carboxylic Acid Derivatives 3/19

Physical Properties

  • amides have highest boiling point because carboxylic acids create dimers

  • nitriles have similar boiling point to alcohols.

  • as we go up in weight, boiling points go up.

  • larger and larger sizes= dipole-dipole attraction in ester become less important

Nitriles

  • So polar because there are two pi bonds. Pi electrons aren’t held super tight so it can create a significantly larger dipole than expected, therefore, can form dimer like structures

  • Linear molecule so it can stack very well, increasing its boiling point

Amides

  • Interactions between amides are very strong. Creates long extended networks that stabilize the amide structure, enhancing their thermal stability and contributing to the high melting and boiling points observed in these compounds.

  • Protein is a peptide with a purpose that refers to a chain of amino acids linked by amide bonds (peptide bonds), and their three-dimensional structure is crucial for biological function.

  • Hydrogen bonding along backbone is what keeps the protein in its shape, allowing for the formation of alpha helices and beta sheets, which are essential elements of protein secondary structure. UV light breaks these hydrogen bonds, change shape, and become peptides

Solubility

  • acid derivatives are soluble in common organic solvents such as alcohols, ethers, chlorinated alkanes, and aromatic hydrocarbons

  • acid chlorides and anhydrides will react with nucleophilic solvents such as alcohols

  • small esters, amides, and nitriles are water soluble due to their high polarity and hydrogen bonding

Nucleophilic Acyl Substitution

Go through for basic or neutral conditionsFor acidic conditions, must protonate first then form intermediate
  • Substitution dependent on leaving group and the charge on the carbonyl carbon

    • more positive carbon is= faster attack

    • better leaving group= faster attack (conjugate base of a strong acid, I>Br>Cl>F

Most positive carbon=acid halideSki lift analogy