Organic Chemistry textbooks and online homework systems

1. Organic Chemistry textbooks and online homework systems Justin Houseknecht (Wittenberg University, Ohio)

2. Overview • Eight best-selling organic textbooks • Listed on next slide • Focus on organization • Corresponding online homework systems • Cengage’s OWL – McMurry • McGraw Hill’s Connect Plus – Carey, Smith • Pearson’s Mastering Chemistry – Bruice, Wade • Wiley’s Wiley Plus – Klein, Solomons • Sapling Learning – any, McMurry • Web Assign – any, McMurry

3. Which textbook do you currently use? • Bruice, 7thed • Carey, 9thed • Klein, 1sted • Loudon, 5thed • McMurry, 8thed • Smith, 4thed • Solomons, 11th • Wade, 8thed • other

4. Organizational Overview

5. Do you currently teach nomenclature • Consolidated – Bruice • Distributed – others

6. Nomenclature • What are the pros and cons of teaching nomenclature as a single unit instead of the distributed model? • Other textbooks with the consolidated approach?

7. Which statement describes you? • I currently teach nomenclature consolidated and am no more likely to change now than before. • I currently teach nomenclature consolidated and am now considering a distributed approach. • I currently teach nomenclature distributed and am no more likely to change now than before. • I currently teach nomenclature distributed and am now considering a consolidated approach.

8. Do you currently teach the first reaction type as: • Alkenes – Bruice, Loudon, McMurry • Substitution - others

9. First reaction type • What are the pros and cons of teaching alkenes before substitution – elimination reactions? • Other textbooks that present alkene reactions first?

10. Which statement describes you? • I currently teach alkenes first and am not considering change now more than before. • I currently teach alkenes first and am considering change now more than before. • I currently teach substitution first and am not considering change now more than before. • I currently teach substitution first and am considering change now more than before.

11. Do you currently teach chirality: • After alkene reactions – Loudon • Before reactions - others

12. Chirality • What are the pros and cons of teaching chirality after alkene reactions? • Other textbooks that introduce chirality after alkene reactivity?

13. Which statement describes you? • I currently teach alkenes before chirality and am not more likely to teach chirality first now. • I currently teach alkenes before chirality and am now more likely to teach chirality first. • I currently teach chirality before reactions and am not more likely to teach alkenes first now. • I currently teach chirality before reactions and am now more likely to teach alkenes first.

14. Do you teach spectroscopy: • After aromatics and before carbonyls – Carey • Before aromatics and carbonyls – others • Lab topic only

15. Spectroscopy • What are the pros and cons of teaching spectroscopy in lecture? • What are the pros and cons of teaching spectroscopy after aromatics rather than prior to aromatics? • What other textbooks approach this in a unique manner?

16. Which statement describes you? • I am unlikely to change how I teach spectscopy based on this discussion. • I am now more likely to start teaching spectroscopy after aromatics. • I am now more likely to start teaching spectroscopy before aromatics. • I am now more likely to start teaching spectroscopy in lecture. • I am now more likely to stop teaching spectroscopy in lecture.

17. Do you currently teach aromatics: • After carbonyls – Bruice • Before carbonyls - others

18. Aromatics • What are the pros and cons of teaching aromatics after carbonyl chemistry? • What other textbooks introduce aromatics after carbonyl chemistry?

19. Which statement describes you? • I teach aromatics before carbonyls and am not more likely to teach carbonyls first now. • I teach aromatics before carbonyls and am now more liokely to teach carbonyls first. • I teach carbonyls before aromatics and am not more likely to teach aromatics first now. • I teach carbonyls before aromatics and am now more likely to teach aromatic first.

20. Do you currently teach carbonyls: • CA’s  Ald/Ket  a-carbonyls - Bruice • Ald/Ket  CA’s  a-carbonyls - others • Ald/Ket  a-carbonyls  CA’s

21. Carbonyls • What are the pros and cons of teaching carboxylic acids and their derivatives before aldehydes and ketones? • What are the pros and cons of teaching a-carbonyl reactions before carboxylic acids and their derivatives? • What other textbooks have unique approaches to carbonyl chemistry?

22. Which statement describes you? • I am not considering a change in how I teach carbonyl chemistry based on this conversation. • I am now considering teaching CA’s and their derivatives first. • I am now considering aldehydes and ketones first. • I am now considering teaching a-carbonyl chemistry before CA’s and their derivatives.

23. Other Unique Features • Green Chemistry • Bruice, Loudon, McMurry, Smith, Wade • Combinatorial Chemistry • Carey and McMurry • Mid-text Introduction of MO Theory • Carey and Smith

24. Online Homework Systems • Relevance • Examined Aldehydes and Ketones chapters of: • Cengage’s OWL – McMurry • McGraw Hill’s Connect Plus – Carey, Smith • Pearson’s Mastering Chemistry – Bruice, Wade • Wiley’s Wiley Plus – Klein, Solomons • Sapling Learning – any, McMurry • Web Assign – any, McMurry

25. What online homework system do you currently use? • OWL (Cengage) • Connect Plus (McGraw-Hill) • Mastering Chemistry (Pearson) • Wiley Plus (Wiley) • Sapling Learning • Web Assign • None

26. Quantitative Results

27. Quantitative Results (cont)

28. (Non)Unique Features • Randomized questions • Hints and feedback • Improved student outcomes

29. Unique Features • OWL (Cengage) • Instruction oriented – Simulations and Tutorials • Very little synthesis practice • Easy to use / few choices • Includes many end-of-chapter questions • WileyPLUS • Opposite OWL – 32 RANDOM synthesis questions • 14 random mechanism questions + linked mechanisms • Includes most book questions, all test bank questions

30. Unique Features • Connect and LearnSmart (McGraw-Hill) • Connect is mostly book questions, but not all questions from book are included • More multiple choice • Drawing interface was frustrating • LearnSmart useful for student self-assessment • Mastering Chemistry (Pearson) • Primarily book and test bank questions • Apparently no random items, but easy to pool

31. Unique Features • Sapling Learning • Between OWL and WileyPLUS • Answers not available online (?) • Well-balanced • Web Assign • Rather limited wrt mechanism and synthesis

32. Conclusions • Most are highly viable options with OWL and WileyPLUS impressing me the most. • I’m happy to show anyone around these systems later today or tomorrow.

33. Acknowledgments • Kevin Bond, Wittenberg class of 2014 • Zach Gamble, Sapling Learning • Sean Hickey, University of New Orleans, WileyPLUS • Stephanie Kahle, McGraw Hill