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

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

Which textbook do you currently use? Bruice, 7th ed Carey, 9th ed Klein, 1st ed Loudon, 5th ed McMurry, 8th ed Smith, 4th ed Solomons, 11th Wade, 8th ed other

Organizational Overview Book Nomenclature First RxN Chirality Spectroscopy Aromatics Carbonyls Bruice Consolidated Alkenes before reactions before carbonyls after carbonyls NAS before addition Carey Distributed Substitution after aromatics Addition before NAS Klein Distibuted before aromatics Loudon after alkenes McMurry Smith Solomons Wade

Do you currently teach nomenclature Consolidated – Bruice Distributed – others

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?

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.

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

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

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.

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

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

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.

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

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?

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.

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

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

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.

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

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?

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.

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

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

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

Quantitative Results Random? OWL Sapling Web Assign Wiley Plus Mastering Chemistry Connect Nomenclature yes 2 9  20   no 15 1 54 42  11 Provide Products 10 5 60  22 128 159  26 Provide Reagents 4 3 62 28  14 Classify 13 16 20  31 ID Unknowns 6 Equilibrium  7

Quantitative Results (cont) Random? OWL Sapling Web Assign Wiley Plus Mastering Chemistry Connect Mechanism yes   54 no 10 5 1 11 59  Structural 18 15 24  Spectroscopy 6 3  28 Relative Reactivity 4  3 Optical Rotation Multistep Synthesis Steps 32 40 84  54 27

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

Unique Features OWL (Cengage) WileyPLUS 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

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

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

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.

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