Lecture23outline-1 - I Review In the presence of base and...

Info icon This preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
I. Review • In the presence of base and alcohol, carboxylic acids only undergo deprotonation and do not react further • In the presence of acid and alcohol, carboxylic acids are activated toward nucleophilic attack that leads to a tetrahedral intermediate that ultimately yields an ester (Fischer esterification) • Esters and acids are similar thermodynamically, so esters can be hydrolyzed to acids in the presence of water • The mechanism of this reaction is exactly the reverse of the mechanism for esterification • When hydroxy groups are in the same molecule as a carboxylic acid, strong acid catalyzes intramolecular nucleophilic addition to form cyclic esters called lactones • Amines react with carboxylic acids to form ammonium carboxylates that leave behind small concentrations of the reactants • Due to the low concentrations of the reactive species, amide formation from amines and acids requires heating • Acid chlorides can be formed by heating carboxylic acids with SOCl 2
Image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern