ORGANIC CHEMISTRY TEXTBOOKS AND ONLINE HOMEWORK SYSTEMSJustin 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?

11%11%

11%

11%11%11%

11%

11%11%

1 2 3 4 5 6 7 8 9

1. Bruice, 7th ed2. Carey, 9th ed3. Klein, 1st ed4. Loudon, 5th ed5. McMurry, 8th ed6. Smith, 4th ed7. Solomons, 11th

8. Wade, 8th ed9. 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 before reactions

after aromatics

before carbonyls

Addition before NAS

Klein Distibuted Substitution before reactions

before aromatics

before carbonyls

Addition before NAS

Loudon Distributed Alkenes after alkenes before aromatics

before carbonyls

Addition before NAS

McMurry Distibuted Alkenes before reactions

before aromatics

before carbonyls

Addition before NAS

Smith Distributed Substitution before reactions

before aromatics

before carbonyls

Addition before NAS

Solomons Distributed Substitution before reactions

before aromatics

before carbonyls

Addition before NAS

Wade Distributed Substitution before reactions

before aromatics

before carbonyls

Addition before NAS

Do you currently teach nomenclature

1 2

50%50%1. Consolidated – Bruice

2. 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?

25%

25%

25%

25%1. I currently teach nomenclature

consolidated and am no more likely to change now than before.

2. I currently teach nomenclature consolidated and am now considering a distributed approach.

3. I currently teach nomenclature distributed and am no more likely to change now than before.

4. I currently teach nomenclature distributed and am now considering a consolidated approach.

Do you currently teach the first reaction type as:

1 2

50%50%1. Alkenes – Bruice, Loudon, McMurry

2. 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?

25%

25%

25%

25%1. I currently teach alkenes first and

am not considering change now more than before.

2. I currently teach alkenes first and am considering change now more than before.

3. I currently teach substitution first and am not considering change now more than before.

4. I currently teach substitution first and am considering change now more than before.

Do you currently teach chirality:

1 2

50%50%1. After alkene reactions – Loudon

2. 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?

25%

25%

25%

25%1. I currently teach alkenes before

chirality and am not more likely to teach chirality first now.

2. I currently teach alkenes before chirality and am now more likely to teach chirality first.

3. I currently teach chirality before reactions and am not more likely to teach alkenes first now.

4. I currently teach chirality before reactions and am now more likely to teach alkenes first.

Do you teach spectroscopy:

1 2 3

33% 33%33%1. After aromatics and before carbonyls – Carey

2. Before aromatics and carbonyls – others

3. 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?

20%

20%

20%

20%

20%1. I am unlikely to change how I teach spectscopy based on this discussion.

2. I am now more likely to start teaching spectroscopy after aromatics.

3. I am now more likely to start teaching spectroscopy before aromatics.

4. I am now more likely to start teaching spectroscopy in lecture.

5. I am now more likely to stop teaching spectroscopy in lecture.

Do you currently teach aromatics:

1 2

50%50%1. After carbonyls – Bruice

2. 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?

25%

25%

25%

25%1. I teach aromatics before carbonyls and am not more likely to teach carbonyls first now.

2. I teach aromatics before carbonyls and am now more liokely to teach carbonyls first.

3. I teach carbonyls before aromatics and am not more likely to teach aromatics first now.

4. I teach carbonyls before aromatics and am now more likely to teach aromatic first.

Do you currently teach carbonyls:

1 2 3

33% 33%33%1. CA’s Ald/Ket a-carbonyls - Bruice

2. Ald/Ket CA’s a-carbonyls - others

3. 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?

25%

25%

25%

25%1. I am not considering a change in how I teach carbonyl chemistry based on this conversation.

2. I am now considering teaching CA’s and their derivatives first.

3. I am now considering aldehydes and ketones first.

4. I am now considering teaching a-carbonyl chemistry before CA’s and their derivatives.

Other Unique Features

Green 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?

1 2 3 4 5 6 7

14% 14% 14% 14%14%14%14%1. OWL (Cengage)2. Connect Plus

(McGraw-Hill)3. Mastering

Chemistry (Pearson)

4. Wiley Plus (Wiley)5. Sapling Learning6. Web Assign7. None

Quantitative Results

Random? OWL Sapling Web Assign

Wiley Plus

Mastering Chemistry Connect

Nomenclatureyes 2 9 2 20 no 15 1 54 42 11

Provide Products

yes 10 5 60 no 11 22 10 128 159 26

Provide Reagents

yes 1 4 3 no 11 2 4 62 28 14

Classifyyes 13 no 16 5 20 31

ID Unknownsyes 1 no 3 6 2

Equilibriumyes no 4 1 7 1

Quantitative Results (cont)

Random? OWL Sapling Web Assign

WileyPlus

Mastering Chemistry Connect

Mechanismyes 54 no 10 5 1 11 59 11

Structural no 18 1 5 15 24 5Spectroscopy no 6 3 10 28 10

Relative Reactivity no 6 1 4 4 3 6

Optical Rotation no 3

Multistep Synthesis Steps

yes 32 no 15 40 4 84 54 27

(Non)Unique Features

Randomized questions Hints and feedback Improved student outcomes

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

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 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