Web-Based Interactive Orgnaic Chemistry Homework

Web-based programs have the potential to change the way we teach sdence, but for instructors to invest the time and resources required to adopt them, such programs must have greater pedagogical value than traditional methods. We have developed a Web-based interactive organic chemistry program, ACE Organic (formerly EPOCH), that is unique and uniquely useful in several ways. ACE generally requires a student to draw a chemical structure or a sequence of chemical structures, and, if a student's response is incorrect, ACE provides feedback that explains why the response is incorrect and makes suggestions to guide the student to the correct answer. Over the last 2.5 years, we have added the following new question types to ACE, which were incorporated into the commercial version of ACE in early 2007: * Mechanism questions. Students can now draw a sequence of chemical structures and curved arrows representing electron flow, just as they do on paper. * Conformation questions. Students can now draw or modify a chemical structure with three-dimensional information. * Lewis structure questions. Our standard drawing tool, MarvinSketch®, adds unshared electrons and implicit H atoms automatically and alerts students to valence errors. We have now developed a new, much less chemically aware drawing tool to permit students to draw (correct and incorrect) Lewis structures. * Label-the-atom questions. Students can now mark the atom in a structure that is most acidic, most nucleophilic, etc., or they can mark every stereogenic atom, or they can label every atom according to its hybridization or stereotopicity. * Multiple-choice, fill-in-the-blank (with pulldown menus), and rank-in-order questions. We now propose adding the following new question types to ACE. * Multistep synthesis questions. Students will be given a target, a description of permissible starting materials, and a set of permissible reagents, and they will design and draw a multistep synthetic scheme. * Free-response questions. Students will explain a concept in natural English, and ACE will evaluate the response and give appropriate feedback. We also plan to evaluate the effectiveness of the recently added question types in improving students' performance in courses. Evaluations of ACE by third parties have suggested that ACE does have a measurable and positive effect on students' understanding of and ability in organic chemistry. Intellectual merit: We will continue to develop and evaluate a Web-based homework program designed for organic chemistry that already has far greater capabilities than any program heretofore developed. Broader impact: We have created a unique and uniquely valuable teaching and learning tool for a difficult course that is taken by large numbers of students across a wide variety of disciplines, and we will continue to expand is scope to reach all corners of the course. Our partnership with the Prentice Hall division of Pearson Education, which funded the initial development of ACE and continues to invest in its support and evaluation, will permit wide dissemination of future versions of ACE.