Two-Cycle Organic Textbook Project

 

  Prospectus

My objective is to create a unique text that complements the two-cycle pedagogy for teaching organic chemistry. All of the available organic textbooks are organized by either functional group or mechanistic type. The two-cycle pedagogy, a hybrid of these two approaches, has two major educational advantages. Most significantly, students learn and demonstrate the ability to apply more organic chemistry when taught using the two-cycle approach. This enhanced outcome has been observed by those educators who utilize this pedagogy and has been documented in the chemical education literature (1). Additionally, the two-cycle approach provides curricular flexibility for primarily undergraduate institutions that can only staff one organic chemistry sequence for all majors(2). This system allows majors taking only one semester of organic chemistry, and majors requiring two semesters of organic chemistry to take the same first organic course. The available organic texts, however, fail to meet this need because either their first halves do not cover all the functional groups or they do not emphasize the necessary physical properties, essential in a one-semester organic course.

The two-cycle pedagogy of this text, proposed in the mid-1980's and fully described in 1992, melds the traditional functional group and mechanistic approaches. In this pedagogy, the two halves of the text, which represent the two semesters of sophomore organic chemistry, are distinct. The first half of the text takes an overview of organic chemistry that employs the functional group approach, including the rigorous coverage of stereochemistry, aromaticity, and spectroscopy necessary for biology and chemistry majors. The second half of the text utilizes a mechanistic approach organized around chemical reactivity. This comprehensive, but not exhaustive sequence examines the major reaction types, emphasizing the energetics through acid/base, nucleophile/electrophile, and molecular orbital analysis. This approach seeks to build chemical reasoning skills by building upon and emphasizing the underlying principles.

This text will be infused with extensive examples and real-world applications, emphasizing biochemical contexts and green chemistry applications. Biochemical examples will be employed to explain and reinforce concepts intriguing the high percentage of biology and pre-professional students while the use of green chemistry will compliment traditional chemistries, offering novel and timely options for chemistry students. Outlines of this text have been successfully class tested over the past eight years in my classes. This text will contain suitable in-chapter problems and sufficient end-of-chapter problems. A long-term goal is to support this text with web-based ancillaries, including homework and an exam bank. These qualities and ancillaries will create a strong and unique product.

(1) Sartoris, N. E. J. Chem. Educ. 1992, 69, 750-752.

(2) Minter, D. E..; Reinecke, M. G. J. Chem. Educ. 1985, 62, 77-79.

  Table of Contents                      Chapter Samples                         Answers to Problems


  FAQ's


What are the advantages of teaching organic with the 2-cycle pedagogy?


Students learn and retain more organic chemistry when taught using the two-cycle approach. This enhanced outcome has been observed by those educators who utilize this pedagogy and has been documented in the chemical education literature. (Sartoris, N. E. J. Chem. Educ. 1992, 69, 750-752.)

 

How does the first half of the text differ from a one-semester organic text or a GOB text?


This text provides a rigorous presentation of stereochemistry, aromaticity, and spectroscopy appropriate to chemistry and other science majors. The emphasis is on mastering the vocabulary of functional groups and understanding their physical and chemical properties before utilizing this information in a systematic examination of mechanistic organic reactions. Biochemical molecules are introduced, acknowledging their organic functional groups, but their biochemical transformations are not emphasized.

 

Are chemical reactions taught in the first half of this text?

Yes. This text presents formation and identification reactions for each functional group.

 

Why are there no reaction mechanisms presented in the first half of the text?


While the physical-organic description of why and how each reaction occurs is not emphasized, the text presents reactions in a manner designed to train students to focus on functional groups as reaction centers. Overall, this pattern recognition provides a solid foundation for the physical-organic description of reactions in the second half of this text.

 

Where is the multistep synthesis?


The second half of the text, starting with chapter 20, contains the majority of the multistep synthesis. While examples of multistep synthesis occur in the first half of the text, this concept ties the mechanistic chapters together and keeps reaction knowledge fresh.

 

Is the early presentation of spectroscopy essential for the rest of the text?


No. Spectroscopy is introduced early and then provided as a means of characterization at the end of each functional group chapter to provide flexibility. Spectroscopy can be effectively presented at any time in the first semester to prepare students for a better understanding of the mechanistic portion of organic chemistry.

 

What changes need to be made to the laboratory to use the 2-cycle pedagogy?


For most instructors, the 2-cycle pedagogy requires very few content changes to their laboratory. Typically, changing the experiment sequence enables a facile transition to the 2-cycle pedagogy.