{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Solutions_Manual_for_Organic_Chemistry_6th_Ed 463

Solutions_Manual_for_Organic_Chemistry_6th_Ed 463 - 19-49(a...

Info icon This preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
19-49 (a) When guanidine is protonated, the cation is greatly stabilized by resonance, distributing the positive charge over all atoms (except H): N H 1 NH 2 NH 2 NH2 .. II .. w .. II .. .. I .. + I H,N-C-NH, H,N-C-NH, �H,N- -NH, �H'N= NH, NH, } I + H2N-C=NH2 . (b) The unprotonated molecule has a resonance form shown below that the protonated molecule cannot have. Therefore, the unprotonated form is stabilized relative to the protonated form. This greater stabilization of the unprotonated fonn is reflected in weaker basicity. .. -o + / / . H2N N - \ :0: .. (c) Anilines are weaker bases than aliphatic amines because the electron pair on the nitrogen is shared with the ring, stabilizing the system. There is a steric requirement, however: the p orbital on the N must be parallel with the p orbitals on the benzene ring in order for the electrons on
Image of page 1
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