Electrophilic Aromatic Substitution – Nitration of Bromobenzene

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Electrophilic Aromatic Substitution – Nitration of Bromobenzene Summary: This reaction demonstrates the nitration of bromobenzene by electrophilic aromatic substitution and allows students to test the directing effects of a bromo substituent. The reaction is carried out using concentrated sulfuric and nitric acids. Reference: Nitration of Bromobenzene, Experimental Organic Chemistry, Gilbert and Martin, 5th Edition, p. 515 Chemical Name Amount per Purchasing cost per Aldrich Catalog # 100 100 students ($) students (g EH&S or mL) Bromobenzene B57702 800mL $17.49 Sulfuric acid, conc. 258105 305mL $6.28 *C Nitric acid, conc. 438073 200mL $7.86 Ethanol, 95% 459836 1250mL $58.13 Electrophilic Aromatic Substitution of Salicylamide – A Greener Approach Summary: This reaction allows for students to study the directing effects of electron donating and electron withdrawing groups on the substitution of a benzene ring by using sodium iodide and household bleach (sodium hypochlorite). Reference: A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory, Eby, E. and Deal, S. T., Green Chemistry, 2008, 85, 1426-1428 Chemical Name Amount per Purchasing cost per Aldrich Catalog # 100 100 students ($) students (g EH&S or mL) Salicylamide 50 g 860417 $14.90 Ethanol, absolute 1000 mL 459836 $77.50 Sodium iodide 60 g 383112 $19.27 * Sodium hypochlorite (6% w/v) 10 mL 239305 $23.63 * Hydrochloric acid, 10% 250 mL $0.98 320331 Ethanol, 95% 500 mL $38.75 459836 Comparison: Electrophilic Aromatic Substitution Comparison of greener and traditional lab: • Greener method eliminates the use of concentrated sulfuric and nitric acid and bromobenzene • Greener method employs a guided-inquiry approach Purchasing costs Waste (per 100 “Greener” benefits students) Greener method $175.03 1.9 L liquid waste Traditional method $89.76 2.5 L liquid waste Other greener lab options to explore: • A simple and practical halogenation of activated arenes using potassium halide and oxone in water- acetonitrile medium, Synth. Comm. 2001, 31 (13), 2021-2027 * Very high hazard EHS Key: Physical hazard High hazard Toxicity/Health hazard Moderate hazard PBT Low hazard No data.

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Vapor Phase Nitration of Butane in a Fused Salt Reactor Frank Slates Adams Iowa State University
Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1961 Vapor phase nitration of butane in a fused salt reactor Frank Slates Adams Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Chemical Engineering Commons Recommended Citation Adams, Frank Slates, "Vapor phase nitration of butane in a fused salt reactor " (1961). Retrospective Theses and Dissertations. 2472. https://lib.dr.iastate.edu/rtd/2472 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. This dissertation has been 61-6173 microfilmed exactly as received ADAMS, Jr., Frank Slates, 1931— VAPOR PHASE NITRATION OF BUTANE IN A FUSED SALT REACTOR. Iowa State University of Science and Technology Ph.D., 1961 Engineering, chemical University Microfilms, Inc., Ann Arbor, Michigan VAPOR PHASK NITRATION OF BUTANE IN A FUSED SALT REACTOR by Frank Slates Adams, Jr. A Dissertation Submitted to the Graduate Faculty in Partial Fulfillment of The Requirements for the Degree of DOCTOR OF PHIDSOPHÏ Major Subject: Chemical Engineering Approved: Signature was redacted for privacy. In Charge of Major Work Signature was redacted for privacy. Head of Major Department Signature was
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