Experiment 7 Electrophilic Aromatic Substitution Of Salicyamide

Improved Essays
Experiment 7
Electrophilic Aromatic Substitution Of Salicyamide
Name: Lidia Santiana Palha
Student number: s3333523
Email-address: lidiapalha@gmail.com
Name of demonstrator: H.Helbert

Reaction Equation Summary

Salicylamide and sodium iodide are dissolved in ethanol, and stirred and cooled to 0.
After that household bleach was added while stirring vigorously, solution changed from colorless to pale yellow. Sodium thiosulphate and hydrochloric acid were added aswell.
Product collected by vacuum filtration and recrystallized from 96% ethanol. IR- and H-
NMR-spectrum were taken to determine the location of the I+. I had a yield of 0,7 g
(2,66mmol, 18,2%). The iodide’s position is opposite of the –OH group.

Salicylamide
…show more content…
Sodium thiosulphate and hydrochloric acid were added aswell.
Product collected by vacuum filtration and recrystallized from 96% ethanol. IR- and H-
NMR-spectrum were taken to determine the location of the I+. I had a yield of 0,7 g
(2,66mmol, 18,2%). The iodide’s position is opposite of the –OH group.

Salicylamide and sodium iodide are dissolved in ethanol, and stirred and cooled to 0.
After that household bleach was added while stirring vigorously, solution changed from colorless to pale yellow. Sodium thiosulphate and hydrochloric acid were added aswell.
Product collected by vacuum filtration and recrystallized from 96% ethanol. IR- and H-
NMR-spectrum were taken to determine the location of the I+. I had a yield of 0,7 g
(2,66mmol, 18,2%). The iodide’s position is opposite of the –OH group.
Salicylamide and NaI were dissolved in ethanol and cooled in a water bath. Then household bleach was added while stirring vigorously. Then NaOCl and HCl were added as well. Product was collected by vacuum filtration and then recrystallized from 96% ethanol and obtained a yield of 2,07g (54%). IR- and H-NMR-spectrum were taken. The Iodide is in the para position (also known as 5-iodosalicylamide), this is confirmed by the IR and the
…show more content…
The second part is the reformation of the double bond. Since iodide is a large atom, it can’t be just placed anywhere, according to the resonance structures, the most stable is C (in Fig.2).
The most stable is C, because the OH and the NH2 give steric hindrance. Also because –OH is a strong activating group (electron donating substituent) and the NH2 is a deactivating group (withdraws electrons from the ring). Therefore –OH is ortho, para directing and -NH2 is meta deactivating. With all this in mind, positions 3 and 5 are more likely (on carbon 2 and 4 on the NMR). 5 is more likely and not 3 because of steric hindrance.
Experimental
In a 100ml round bottomed flask, salicylamide (2.0g, 14.6mmol, 1eqiuv) and sodium iodide (2.4g, 16mmol, 1.1equiv) were dissolved in absolute ethanol (40ml). The solution was stirred and cooled to 0°C using a water bath. The flask was removed from the ice bath then household beach (4%, 272.2ml, 1.2equiv) was added to the solution while stirring vigorously. Solution changed from colourless to dark red-brown to pale yellow. After a short time, sodium thiosulfate (10%, 10ml) was added. HCL (10%, 10ml) was added to acidify the reaction. The precipitate was collected by vacuum filtration and recrystallized from ethanol (96%). Both starting and product

Related Documents

  • Great Essays

    The ter-polymerization solution was left for 24 hr at room temperature to complete the polycondensation reaction. Ammonia solution, 10 mL of 33 % NH4OH diluted by 20 mL of distilled water, was added drop wisely until a deep brown precipitate was produced. The filtered precipitate (EB) was washed with sufficient amount of deionized water then washed by ethanol to remove residual oxidant, unreacted monomer and oligomer until the filtrate became colorless and oven dried at 60 °C for overnight. The deep brown dried powder produces PANI-AA-o-PDA (PAAAPDAK1). The gained terpolymer yield was calculated to be 88.3 % utilizing the subsequent compatible…

    • 1458 Words
    • 6 Pages
    Great Essays
  • Improved Essays

    Ethyl vinyl ether was used to protect –OH on glycidol based on a literature reported protocal.59 In a typical procedure, 0.675 mol glycidol and 200 mL ethyl vinyl ether were loaded in a round-bottom flask, to which 1.25 g TsOH was then added. The reaction was allowed to proceed at room temperature (RT) for 3h. The resulting mixture was then purified by washing with 100 ml saturated aqueous solution of NaHCO3 for 3 times. The organic layer obtained was dried by MgSO4. After filtration of MgSO4, the excess ethyl vinyl ether was removed by rotary evaporation.…

    • 988 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    Water content : The American Society for Testing and Materials(ASTM) standard method D95 was used from ensuring the water content of the oily sludge. The oily sludge was heated with benzene(solvent) which co-distilled with the water in the sample in a fume cupboard .Condensed solvent and water were continuously separate and the water settled as the bottom layer. The condensed liquid containing water and hydrocarbon was transferred to a graduated cylinder. A water layer with higher density was at the bottom of the cylinder. The volume of the water was then used in calculating the water content in the sample (using the density of water of 1g/cm3 ).…

    • 935 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    Step 2-Synthesis Essay

    • 1160 Words
    • 5 Pages

    Here the gas mixture is introduced at the bottom of a column and passed up through a counter-current of cold water. 96% of the ammonia in the gas is absorbed by the water, leaving a gas mixture that is used as a fuel gas to heat the primary reformer. The ammonia is distilled out of the ammonia-water mixture, condensed and then pumped to join the rest of the ammonia from the ammonia synthesizer. Urea manufacturing 1) Heat recovery The heat of the reaction in which ammonium carbamate produces steam at 7 brag. This is used in the decomposition and evaporation sections for…

    • 1160 Words
    • 5 Pages
    Improved Essays
  • Improved Essays

    Urea Synthesis Lab Report

    • 988 Words
    • 4 Pages

    This liquid effluent is let down to 27 atm and fed to a special flash-evaporator containing a gas-liquid separator and condenser. Unreacted NH3, CO2 and H2O are thus removed and recycled. An aqueous solution of carbamate-urea is passed to the atmospheric flash drum where further decomposition of carbamate takes place. NH2COONH4 2NH3 + CO2 The pressure is then reduced and a solution of urea dissolved in water and free of other impurities remains. At each stage the unconsumed reactants are absorbed into a water solution which is recycled to the secondary reactor.…

    • 988 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    Bacillus Subtilis

    • 1799 Words
    • 8 Pages

    Remove the cap from the bottle containing the culture of Bacillus subtilis. Pass the neck through the Bunsen burner flame 2-3 times. Remove a few drops of culture with the sterile dropping pipette. Flame the bottle neck again and replace the cap. Lift the lid of the Petri dishes.…

    • 1799 Words
    • 8 Pages
    Improved Essays
  • Decent Essays

    Stir the solution and heat it until the solid dissolves. Now add 6.5 mL of HCl to this solution. Cool thoroughly in an ice-water bath. In a separate beaker, make up a solution of 3.7 g of sodium nitrite in 10 mL of water. Take a small beaker and weigh out about 5 g of ice and pour it into the conical flask having the reaction mixture.…

    • 2234 Words
    • 9 Pages
    Decent Essays
  • Improved Essays

    Sulphamic Acid Case Study

    • 2390 Words
    • 10 Pages

    The ammonium bisulphate is separated by the filtration in form of the ammonium sulphate. So it is neutralization of crystallization of the sulphamic acid. The manufacture of sulphamic acid from the reactants urea, sulphuric acid, and SO3 and heated at about 75º C to 85º C. CO (NH2)2 + H2SO4 + SO3 → 2NH2SO3H + CO2 When the sulphur trioxide is reacting with the ammonia, contain amidosulfonic acid and imido-disulfonic acid is obtained. From the resulting solution sulphamic acid precipitates in high give up. (Leclercq, P. & Luternauer, J.…

    • 2390 Words
    • 10 Pages
    Improved Essays
  • Improved Essays

    Isobutylene Research Paper

    • 1817 Words
    • 8 Pages

    MX 2301 is the Mixer in this stage of the process that mixes isobutylene that comes from (V 3101, V 3102) with Methanol from Methanol drum (V 2303). Next, Isobutylene and Methanol reacted in reactor (R 2301) to produce 95% of MTBE at a pressure that equals 3400 kpagauge and temperature of 120o C. In addition, butane column (V 2304) is available and it has two objectives, which are reaching 98% to 99% of MTBE production and distillation of MTBE from other components such as Methanol and unreacted isobutylene. MTBE transferred to the storage tanks and the other compounds go to Water wash column (V 2306). V 2306 is the next column that extracts Methanol from the mixture of Methanol and unreacted Isobutylene. Extraction process occurred by…

    • 1817 Words
    • 8 Pages
    Improved Essays
  • Great Essays

    Dehydration Lab Report

    • 1082 Words
    • 5 Pages

    2. Removing a beta-hydrogen besides the methyl group to form a stable product. 3. The most stable carbocation is a tertiary carbon, which means the major product is going to be a tri-substituted alkene (mendelset.com). The overall reaction for the dehydration of 2-methylcyclohexanol…

    • 1082 Words
    • 5 Pages
    Great Essays