multi-step synthesis uses aniline as the starting reagent to synthesize five compounds employing several reactions such as acetylation‚ diazo coupling‚ nitration‚ bromination‚ and hydrolysis. The isolated products were analyzed with TLC and spectral data that determined most products were pure while some had a few impurities indicated by GC‚ LC‚ and a wide melting point range was shown for products 2 and 3. The presence of water in product 2 and 7 was indicated by the IR. Acetanilide and diazoaminobenzene
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Introduction:The purpose of this lab was to determine the activating effect of aniline‚ phenol‚ anisole and acetanilide after reacting with pyridinum tribromide in order to undergo electrophilic aromatic substitution. The melting point of the isolated products were measured against the standards in order to determine how strong of an ortho/para activator the compound was based on the product(s) and melting point obtained. Theory: Electrophilic aromatic substitution is an organic reaction that takes
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Relative Reactivity of Anilines Abstract: Various Anilines were tested with Br2/HBr solution‚ the products were crystallized and melting points attained to verify relative reactivity. My assignment‚ 2‚4-Dibromoanisol‚ was prepared in a yield of 52% with a melting point of 55-58 C . Reaction: Mechanism: Procedure: Anisole (0.35mL‚ 0.0378mol) was obtained and placed in a pre-weighed 25 mL round bottom flask‚ along with 2.5 mL of glacial acetic acid and a magnetic stir bar. Then the
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BROMINATION OF ACETANILIDE OBJECTIVE Aim of the experiment was too brominate acetaldehyde to form p-bromoacetanilide. INTRODUCTION Acetanilide is a chemical compound with the chemical formula of C6H5NH(COCH3). It is a crystalline solid that is prepared by acetylation of analine and is widely used in the dye industry. This crystalline solid is an odourless solid chemical that has a flake or leaf like appearance. It is also known as N phenylacetamide‚ acetanil or acetanilide. Its former
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Synthesis of Acetanilide By: Rick Whitely April 9‚ 2013 Organic Chemistry Lab 1; Professor J. Hutchison Recrystallization is a common method of purifying organic substances through the differences in solubility at different temperature. In this experiment‚ acetanilide was produced by acetylation of aniline with acetic anhydride. The crude acetanilide was dissolved in a solvent in a heated water bath. The solution was cooled slowly in an ice bath as crystals form out. As the compound crystallizes
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Synthesis of Acetanilide Reaction O NH2 + H3C C O O C CH3 O N C CH3 H + H3C O C OH Aniline Acetic anhydride Acetanilide Acetic acid Purpose: Acetanilide is a useful precursor to many pharmaceuticals such as acetaminophen and penicillin. Experimental Procedure. (Estimated time: 1.5 h.) Unless otherwise noted‚ all manipulations should be done in the chemical fume hood. Place 100 µL of aniline into a tared 10 X 75-mm test tube (standing in a small beaker or Erlenmeyer flask). Now add
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Learning Activity 1 Preparation of Acetanilide Abstract Recrystallization is a common method of purifying organic substances through the difference in solubility at different temperature. In this experiment‚ acetanilide was produced by acetylation of aniline with acetic anhydride. The crude acetanilide was dissolved in a solvent in a heating water bath. The solution was cooled slowly in an ice bath as crystals form out. As the compound crystallizes from the solution‚ molecules of other compounds
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Bromination of Acetanilide Objective: The objective of this experiment was to use melting point and NMR to determine which of two isomers‚ ortho or para‚ would most likely form after brominating Acetanilide through electrophilic aromatic substitution. Procedure/Observations: 1. Weigh out ~280 mg of acetanilide in a 10 mL r.b. flask with a stir bar. 2. Then‚ add 2.0 mL of glacial acetic acid using a calibrated Pasteur pipet. 3. Stir the mixture until all of the acetanilide has dissolved
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Bromination of Acetanilide Introduction: Bromination of acetanilide to 4-bromoaniline was studied in this experiment. One of the most important mechanism with the reaction of aromatic compounds is the electrophilic aromatic substitution reactions(wade‚2013). The electrophilic aromatic substitution enable scientists to make substituted aromatic compounds. However‚ substitution groups affect the electrophilic substitution mechanism. A nitrogen atom attached to hydrogen is learned to be a powerful
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CHEMISTRY 220 PRACTICAL REPORT PRACTICAL 1 Title: Nitration of Acetanilide Aim : To observe how an Aromatic electrophilic Substitution reaction takes place via the nitration of Acetanilide i.e. how hydrogen on a carbon chain is replaced with a nitro group. Reagents and Chemicals: • Acetanilide (5g) • Glacial acetic acid (5mL) • Concentrated sulphuric acid (10mL &1.5mL) • Concentrated Nitric acid (2.0mL) • Methanol (30-50mL) Modification to experimental
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