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The Reactivity and Selectivity of the Reaction of Sulfur Trioxide and Bromobenzene

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The Reactivity and Selectivity of the Reaction of Sulfur Trioxide and Bromobenzene Brigham Young University BYU ScholarsArchive Theses and Dissertations 1970-06-01 The reactivity and selectivity of the reaction of sulfur trioxide and bromobenzene Sullivan E. Blau Brigham Young University - Provo Follow this and additional works at: https://scholarsarchive.byu.edu/etd BYU ScholarsArchive Citation Blau, Sullivan E., "The reactivity and selectivity of the reaction of sulfur trioxide and bromobenzene" (1970). Theses and Dissertations. 8171. https://scholarsarchive.byu.edu/etd/8171 This Dissertation is brought to you for free and open access by BYU ScholarsArchive. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of BYU ScholarsArchive. For more information, please contact [email protected], [email protected]. &.V 1-022-- .. 85? f'J?O THE REltC'I 1IVITY A..1\10SELECTIVITY OF THE REACTION OF SULFUR TRIOXIDE AND BROMOBENZENB A Dissertation Presen·t:.ed to the Department of Cha~istry Brigham Young University \ In Partia.l Fulfillment of the Requirements tor the Degree Doctor of ~hilosophy by Sullivan E. Blau J·une 1970 This dissertation, by Sullivan E. Blau, i.s accepted in its present form by the DepaS"tmeht of Chemistry of Brigham Young University as satisfying the dissertation requirement for the degree of Doctor of Philosophy. ii ACKNOWLEDGMENTS I would like to express appreciation to the staff and faculty in the Department of Chemis·try, Brigham Young University, for cont.inued assistance and support during my tenure here. Dr. K. LeRoi Nelson is due special thanks for his interest, assistance and understanding extended to me in spite of many other responsibilities and demands for his time and consideration. __,_ iii TABLE OF CONTENTS ACKNOWLEDGMENTS• • • • • • • • • • • • • • • • • • • • iii LIST OF TABLES• •• • • • • • • • • • • • • • • • • • • vi LIST OF ILLUSTRATIONS • • • • • • • • • • • • • • • • .viii Chapt,;:r I. INTRODUCTIONAND BACKGROUND • • • • • • • • • • l Electrophilic P..romatic Substitution Reactivity and Selectivity Electrophilic Aromatic Substitution Reactions on Bromobenzene II. AROt-iATIC STJLFO:NATION • • • • • • • • • • • * • • 19 Secondary Reactions Secondary Reactions and Their Effects on Relative Rates Secondary Reactions and Their Effects on Isomer Distribution Kinetic Isotope Effects Reversibility III. RESULTS AND DISCUSSION. • ••••• • • •• • • 39 Sul.fodehalogenation Calculation of Relative Rates 'l'est for 'X'hermodynamic vs. Kinetic Control Analysis of the Data for Secondary Reactions Isomer Distribution for the sulfonation of Bromobenzene Calculation of the Partial Rate Factors Error Ana.lysis iv Chapter Page lV. EXPERIMENTALSECTION • • fj • • • • • • • • • • • 71 Preparation of the' Isomers of Bromo- benzenesulfonic Acid Salts Preparation of Radioactive sulfur Trioxide Preparation of Radioactive Benzene Purification of Benzene and Bromobenzene Sulfonation Procedure Analysis of the Isomer Distribution EXperiments Analysis of Competitive sulfonation EXperiments LIST OF REFER~CES • •••• • • • • • •• • • • • • • • 86 APPENDIXES A. Generation of Data t.o Test the Effects of secondary Reactions .............. 94 B. Design of a Flow Apparatus for the Study of the Bromination of Olefins • • • • • • • • • • J.C.l2 c. A Research Proposal, A Study cf the Stability and Reactions of the Cy,.:!lopentenyl Free Radical ••••••••••••••••• lll D. Manuscript for Publication: Reactivity and selectivity of t'he Reaction of sulfu.t Trioxide and Bro:mobenzene •••••••••• 117 . V LIST OF TABLES Table Page 1. Correlation of Halogenation Rates with Complex Stabilities • • • • • • • • • • • • • • • • • • 8 2. Selectivity and Reactivity of Electrophilic Substitutions on Toluene ••••••••• • • • 10 3. Partial Rate Factors for Electrophilic Substitutions on Bromobenzene ••• • • • • • • 14 4. Reactions Having Large Deviations from the Selectivity Relationship ••••••••• • • • 16 s. Isomerization and Desulfonation of Toluene- sulfonic Acids •••••••••••••• • • • 22 6. Data Generated with a Primary Reaction Rate Ratio of 20, a Secondary Reaction Rate Ratio of 2 and A1/B1 of 1.0 ••••••••••••• 29 · 7. Data Generated with a Primary Reaction Rate Ratio of 20, a Secondary Reaction Rate Ratio of 2 and A1/B 1 of o.s ••••••••••••• 29 s. Data Generated with a Primary Reaction Rate Ratio of 2, a Secondary Reaction Rate Ratio . of 20 and A1/B 1 of 1.0 ••••••••••••• 29 9. Data Generated with a Primary Reaction Rate Ratio of 20, a Seoondary Reaction Rate Ratio of 2 and Ai/B1 of 1.0 ••••••••••••• 35 10. Data Generated with a Primary Reaction Rate Ratio of 20, a Secondary Reaction Rate Ratio of 2 and Ai /Bi of O • 5 • • • • • , • • • • • • • • 3 5 11. Data Generated with a Primary Reaction Rate Ratio of 20, a Secondary Reaction Rate Ratio of 2 and A1/B 1 of 2.0 ••••••••••••• 35 12. Products of the Conversion of Bromobenzene- sulfonic Acid to the Sulfonyl Chloride by Phosphorous Pentachloride •••••••• • • • 43 vi 'l'able Page 13. Products of the Conversion of Iodobenzene- sulfonic Acid to the sulfonyl Chloride by Phosphorus Pentachloride •••••••••••• 44 14. Experimental Data for the Relative Rate 46 Determination of' J.te~eft4\WBrmnobenzene. ' • • • • • 1.5. Relative Rates as Determined for Varying Initial Ratios of Benzene and Bromobenzene • • • 48 16. Equilibriu.~ Constant Calculation to Test Thermodynamic Control ••••••••••••• 50 17. Relative Rate Determination Utilizing Gas Chromatographic Separation of the sulfonyl Chlorides • • • • • • • • • • • • • • • • • • • 52 18. Relative Rate Determination Utilizing Labeled Benzene •••••••••• • • • • • • 53 Moles of the Final Products in the Competitive Sulfonation of Benzene and Bromobenzene •• • • 57 20. Counti.ng Data for the Isomer Distribution Determination • * ••••••••••• • • • • 62 21. Isomer Distribution of Bromobenzenesulfcnic Acid. 64 22. The Isomer Distributions in the Sulfonation of- the Halobenzenes • • • • • • • • • • • • • • 65 23. Ortho/Para Ratios for the Sulfonation of Bromobenzene •••••••••••••• • • • e 65 24. Ortho/Para Ratios for Runs 20 through 24. • • • • 66 25. Partial Rate Factors for the Sulfonation of Bromobenzene ••• • • • • • • • • • • • • • • • 67 26. Isomer Distribution and Partial Rate Factors for Low so3 Concentration •••••••• • • • 68 27. Precision of the Measurements Used in the Calculation of Relative Rates •••••• • • • 69 28. Melting Points of the s-Benzylisothiouronium Salts of the Bromobenzenesulfonic Acids •••• 74 vii -, /~ ,_ ' ;- ,,, A ., • ' LIST OF ILLtiSTRATIONS Figure Page 1. Dewar's Proposed rr-Complex Mechanism for Electrophilic Aromatic Substitutions •• • • • • 2 2. Nelson and Brown•s Mechanism for Electrophilic Aromatic Substitutions ••••••••••• • • 6 3. Energy Diagram for a Typical Electrophilic Aromatic Substitution Reaction ••••• • • • • 7 4. Reactivity and Selectivity of Reagents on Toluene • • • • • • • • • • • • • • • • • • • • 13 s. Extension of the Reactivity-selectivity Diagram to Other Monosubstituted Benzenes ••••••• 13 6. Reactivity and selectivity of Electrophilic Reagents on Bromobenzene •••••••• • • • • 18 7. Christensen's Reaction Sequence for sulfur Trioxide sulfonation Reactions ••••• • • • • 26 a. secondary Reaction Effects in Mechanism I • • • • 30 9. Variations in ASH/BSH in Mechanism I •••• • • • 31 10. Secondary Reaction Effects in Mechanism II. • • • 36 11. Variations in ASH/BSH in Mechanism II • • • • • • 37 12. Chromatogram of the Products of the Brorno- benzenesulfonic Acid Conversion by Phosphorous Pentachloride ••••••••••••••••• 42 13. Apparent Relative Rates as a Function of Initial Benzene/Bromobenzene Ratios •••• e • 47 14. Variations in the Ratio of the Product sulfonic Acids with Sulfur Trioxide concentrations as Determined by Gas Chromatography •••••••• 54 viii Figure Page 15. Variations in the Ratio of the Product sulfonic Acids with Sulfur Trioxide Concentrations as 1 Determined by c 4 Analysis ••••••••• • • 55 16. Moles of Sulfonic Acid Products as a Function of Sulfur Trio..~id~ Cori~entration by Gas Chromatographic Anal~sis •••••••••• • • 58 17. Moles of sulfonic Acid Products as a FUnction of sulfur Trioxide Concentration by cl 4 Analysis •••••••••••••••••• 59 18. Isotope Exchange Reactor ••••• .- ••••••• 75 1 19. vacuum Line for c 4-Benzene Preparation • • • • • 76 20. The Sulfonation Apparatus •••••••••••• 78 21. Calibration of the Flowmeter • • • • • • • • • • • 106 22. The Bromination Apparatus • • • • • • • • • • • • 109 _i..x CHAPTER.I INTRODUCTIONAND BACKGROUND Electro~hilic Aromatic Substitution Considerable research has been dedicated to the detailing of the mechanism of electrophilic aromatic substitution reactions. Although significant success has been achieved in these efforts, there remain a number of points to be clarified. The observations that aromatic hydrocarbons exhibit a significant solubility in liquid hydrogen fluoride, 69 whereas aliphatic hydrocarbons are insoluble under the same conditions, led to the reasonable conclusion that an interaction between the HF and the aromatic system occurs. It was found subsequently that a number of systems showed similar reactions with the aromatic nucleus, silver ion,l hydrogen chloride and hydrogen bromide, 17 among others. McCaulay and Lien76 noted that the solubilit.y of a number of aromatic compounds in liquid HF was greatly increased upon the addition of boron trifluoride. Simj.larJ.y, it was observed that aluminum chloride was not by itself soluble in toluene, but upon the addition of HCl, the solution became intensely colorea. 16 Dissolving aluminun, bromide and HBr in
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