215F07-notes-10-5-07 - Chem 215 F07 Notes Dr Masato Koreeda...

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

View Full Document Right Arrow Icon
Chem 215 F07 Notes – Dr. Masato Koreeda - Page 1 of 4. Date: October 5, 2007 Chapter 15: Carboxylic Acids and Their Derivatives – Acyl Transfer Reactions O R Z an acyl group bonded to an electronegative atom (Z) R OH O carboxylic acid R X O acid halide* X = halogen R O O acid anhydride R OR' O ester R SR' O thioester R NR' 2 O amide R' O R F O R Cl O R Br O acid fluoride acid chloride acid bromide R I O acid iodide * acid halides R C Z O sp 2 hybridized; trigonal planar making it relatively "uncrowded" The electronegative O atom polarizes the C=O group, making the C=O carbon "electrophilic." R C Z O R C Z O R C Z O R C Z O ! ! ! The basicity and size of Z determine how much this structure contributes to the hybrid. hybrid Resonance contribution by Z The more basic Z is, the more it donates its electron pair, and the more resonance structure * contributes to the hybrid. * Trends in basicity: Cl O R' O OH OR' NR' 2 weakest base strongest base increasing basicity similar basicity As the basicity of Z increases, the stability of R Z O increases because of added resonance stabilization.
Image of page 1

Info icon This 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