CH201 LAB 3 P- Bromoacetanilide synthesis ................ PDF

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experiment 3 as described above in the title please open the file and check out the report as the original copy ...............................................................................................................................................................................................

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MELVINA MANSITA KRISHNA S11157774 ORGANIC CHEMISTRY CH201 LAB 3

Pre-Lab

SYNTHESIS OF P-BROMOACETANILIDE Aim P-Bromo Acetanilide Preparation (Brominating reaction). Introduction Brominating of acetanilide can be affected by shaping atomic bromine in a hydrobromic corrosive arrangement with potassium bromate. The acetanilide helpful gathering contains usual reinforced electrons which, by reverberation, will cancel out the carbocation middle of the road utilitarian. As a result, the set is both triggering (reacts faster than benzene) and ortho/para coordinating (so the reverberation adjustment can take place). Under these unmistakably acidic conditions, the typical iron tribromide impetus isn't needed because acetanilide is sufficiently electron-rich (the carbocation is balanced out in acidic media). C8H8BrNO Precious stones soften at 168°C, are solvents of benzene, chloroform, and ethyl acetic acid derivations, and are insoluble in cold-water. They are used as a pain reliever and antipyretic. The ortho- and para-isomers are mixed in the bromoacetanilde object, but the para-isomer is less soluble in this fluid dissolvable and will take form out of solution (Armstrong.2001) Furthermore, the aim of this research is to combine p-bromoacetanilde. The reaction of acetanilide with bromine is seen in the situation below.

Procedure

REACTION:

25/01/16 Preparaon of p -Bromoaniline Equaon 1 NH 2

NH O O

O O

Equaon 2 NH O

Br 2

NH Br 2

O

Equa on 3

Data table (5 m) RESULTS TABLE Reagents Acetanilide

Mr (g/mol) 135.165

Mass (g) 6.75

Moles (mol) 0.05

Volume (mL) 22.5

Bromine

79.90

8.5

0.11

2.65

Glacial acetic acid

60.05

23.625

0.39

22.5

P-Bromo acetanilide

214.062

0.69

0.0032

Calculation Mass of acetanilide = 0.94 g (Experimental Yield) Molar Mass (p-Bromo acetanilide) = n × Mr = 0.0032 mol × 214.062 g/mol = 0.68 g (Theoretical yield) Percentage yield:

Percentage yield

Melting point ⸰ C

138.24 %

160 – 164

Experimental yield/ Theoretical yield × 100% 0.94g/0.68g × 100% Percentage yield= 138.24%

Data analysis and comparison In this experiment, according to the writing, the predicted melting point of p-bromoacetanilde is 159.4 degrees Celsius (Pen Scratch pad science), which is right as opposed to the test range of 120 to 160 degrees Celsius. Furthermore, some real changes were noted when doing the analyses. When cold corrosive was applied to acetanilide, the color changed to purple, and when it was left for a few minutes, the color changed to milky. Since the acetanilide in our bunches was so easily dissolved, there was no need to warm it. Finally, our item's rate yield did not meet our standards because it was incredibly low, which was due to anticipated trial blunders. Post-Lab question 1) Reaction of aniline with liquid bromine Aniline and bromine liquid react to form 2,4,6-Tribromoaniline. As a result, we must exert control over the reaction (to stop joining three bromine atoms to benzene ring and stop it by joining only one bromine atom at para position). if 4-Bromoaniline needs to be prepared. 2) The para product is more prominent and less soluble in water than the ortho product. As a result, the para is readily separated and subjected to acetic group hydrolysis. Conclusion: The final result framed at the conclusion of this trial was p-Bromo acetanilide. The softening point of pBromo acetanilide was discovered to be in the range of 160°C to 164°C, which is close to the writing temperature. Furthermore, the p-bromo acetanilide rate yield was 6.45, which was exceptionally low and did not meet our expectations....