lab4orgo - BRANDEIS UNIVERSITY CHEMISTRY 29A PRELAB WRITEUP...

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BRANDEIS UNIVERSITY CHEMISTRY 29A PRELAB WRITEUP AND EXPERIMENTAL REPORT SHEET NAME_ T.A.’S NAME DATE_________ EXPERIMENT # __4_____ TITLE Nitration of a benzene ring Purpose: To synthesize nitromethyl benzonate by electrophilic aromatic substitution PRELIMINARY WRITEUP* (INCLUDING EQUATIONS, TABLE OF MATERIALS, THEIR AMOUNTS AND CONSTANTS. AND PRELAB QUESTIONS. Place these questions on the reverse of this page) (* use reverse of both sheets if necessary) Substance Purpose Melting Point (degrees Celsius) Molecular Weight (g/mol) Theoretical amount used (g) Other notes Water Removal of water soluble impurities from product, and crystallization N/A N/A N/A Methanol Used to remove impurities from product and as primary solvent for recrysallization (it dissolved the nitro methyl benzoate at high temp and did not at low temp) N/A N/A 0.2 mL + equal weight of product Density = 0.7918g/mL Sulfuric Acid Reacts with nitric acid to form nitronium- complex which leads to nitroinum ion formation, and protonates methyl benzoate to allow for electrophilic substitution N/A N/A 0.2mL + 6mL Nitric Acid Reacts with sulfuric acid and water to form nitronium N/A N/A 0.2mL Nitro Methyl Benzonate product 78 181.15 N/A Water (Ice) To crystallize the product out of the mother liquid N/A N/A 2.5 Nitronium Reactive intermediary used as the electrophile in electrophilic substitution N/A N/A In situ Highly reactive intermediary Methyl benzoate Source a of aromatic ring, requires protonation to activate it for easier electrophilic substitution N/A 136.16 0.3g Density = 1.09g/ mL EXPERIMENTAL PROCEDURES* (include in preliminary writeup) 1. mix 6 mL of sulfuric acid and 0.3 g methyl benzonate in a reaction tube on ice 2. stir completely and cool to 0C 3. mix 0.2mL sulfuric acid and 0.2mL nitric acid on ice 4. add the nitronium solution dropwise to the methyl benzonate solution 5. keep on ice during addition and mix thoroughly
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This note was uploaded on 09/21/2008 for the course CHEM 29B taught by Professor Cziplack during the Spring '08 term at Brandeis.

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lab4orgo - BRANDEIS UNIVERSITY CHEMISTRY 29A PRELAB WRITEUP...

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