{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

POD10Key - important contributing resonance structures not...

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

View Full Document Right Arrow Icon
Problem of the Day #10 Answer Key Deadline : IN CLASS on W 7/28/2010 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Consider the isomerization reaction shown below: Propose a mechanism for this overall transformation. Use curved arrows to show movement of pairs of electrons, and be sure to draw structures of all important reaction intermediates. If a reaction intermediate is a resonance hybrid, please write structures for all
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: important contributing resonance structures, not just the most important one! OH O H O H HO O O A proton on the C atom is removed by the base toyield a resonance-stabilized enolate anion: Reprotonation then occurs on the C atom to yield the rearranged product. The "arrow pushing" is shown using the most important contributing resonance structure of the enolate anion: O O H OH O OH (cat.) H 2 O O...
View Full Document

{[ snackBarMessage ]}

Ask a homework question - tutors are online