HW05Key - If a reaction intermediate is a resonance hybrid,...

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

View Full Document Right Arrow Icon
Graded Homework Problem #05 – Answer Key Deadline : 3:00 p.m., Monday, 2/11/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When the geminal diol shown below is heated in water containing a catalytic amount of sulfuric acid, a reaction occurs which produces water and cyclohexanone as the major products: O H OH H 2 SO 4 (cat.), Δ H 2 O (solvent) O + O H 2 Propose a mechanism to account 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.
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: If a reaction intermediate is a resonance hybrid, it is only necessary to draw the most important contributing resonance structure. You may assume that hydronium (H3O+) is present under the given reaction conditions. (Hint : The mechanism of acid-catalyzed ketone hydration that we discussed in lecture is reversible .) O H OH H O H H O H O H H H O H O H H O H H O H (plus resonance) O H O H H H O H...
View Full Document

This note was uploaded on 04/30/2008 for the course PHY 317L taught by Professor Ritchie/lang during the Fall '08 term at University of Texas at Austin.

Ask a homework question - tutors are online