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Introduction 12 Brief summary of the procedure and its place in the middle school curriculum 15 Constant relevance to real world applications 18 Teacher and student perspectives of the hydrophobicity/fluorophilicity unit 19 Conclusion 23 Hazards 23 CHAPTER 3. Probing the Limitations of Fluorous Content for Tag-Mediated Microarray Formation Abstract Introduction Results and discussion Conclusion Experimental section CHAPTER 4. Automated Solution-Phase Synthesis of the Cell Wall Oligosaccharides of Group A Streptococcus Abstract Introduction iii Results and discussion Conclusion Experimental section CHAPTER 5. Automated Solution-Phase Synthesis of the Cell Wall Oligosaccharides of Staphylococcus aureus Abstract Introduction Results and discussion Conclusion Experimental Section CHAPTER 6. Conclusions and Future Directions ACKNOWLEDGMENTS APPENDIX A. CHAPTER 2 WORKSHEETS 99 APPENDIX B. CHAPTER 3 1 H AND 13 C NMR SPECTRA APPENDIX C. CHAPTER 4 1 H AND 13 C NMR SPECTRA BIBLIOGRAPHY CHAPTER 1 GENERAL INTRODUCTION Dissertation Organization This dissertation is comprised of six different chapters. Chapter 1 is a review of the basic concepts and principles that are involved with chapters 2 thru 5. Chapter 2 reports a hydrophobicity/fluorophilicity unit introduced into the middle school classroom. Chapter 3 discusses the synthetic route of a di-fluorous tag. Comparative studies of the di-fluorous tag versus the mono-fluorous tags were carried out by microarray experiments. Chapter 4 demonstrates the automated solution-phase synthesizer in the synthesis of Group A Streptococcus (GAS) branched oligosaccharide. In chapter 5, Staphylococcus aureus monosaccharides were developed in order to be synthesized by the automated solution-phase synthesizer. This chapter will discuss the difficulties in building the S. aureus monomers and the methodology of the certain protecting groups. Finally, chapter 6 will conclude the dissertation with a summary of the projects and the future directions of each project.