Bromination of Acetanilide Smiley Lab Report PDF

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Experiment 7: Bromination of Acetanilide

Esther Kadoch 1934019

Presented to Roger Machaalani

Dawson College 202-BZF-05 00002

May 5th, 2021 May 12th, 2021

Data and Results:

Mass of acetanilide used (g)

0.5009

Moles of acetanilide used (mol)

3.706 × 10−3

Mass of empty watch glass (g)

31.5695

Mass of watch glass + product (g)

31.9684

Mass of product obtained after

0.3989

recrystallization (g) Percent yield (%)

Melting point of the product (ºC)

Identification of the product formed

50.28

146-159

4-bromoacetanilde

Sample Calculations: 1. Moles of acetanilide:

n =m ÷M = 0.5009 g ÷ 135.16 g/mol 3.706 × 10−3 mol

2. Mass of the product after recrystallization: Mass of watch glass with the product

mass of empty watch glass

= 31.9684 g −31.5695 g = 0.3989 g

3. Theoretical value of 4-bromoacetanilde: Molar ratio of acetanilide and 4-bromoacetanilde is 1:1. Therefore, there is 3.706 × 10−3 moles of 4-bromoacetanilide.

m =n ÷M m = (3.706 × 10−3 mol ) × 214.059 g/mol = 0.7933 g

4. Percentage yield: Percentage yield

(actual value ÷ theoretical value ) ×100 % = (0.3989 g ÷ 0.7933 g ) × 100 % = 50.28 %

Questions: 1. Show the percent yield calculation. Percentage yield

(actual value ÷ theoretical value ) ×100 % = (0.3989 g ÷ 0.7933 g ) × 100 % = 50.28 %

2. Using curved arrow notation, draw all possible resonance structures of acetanilide.

3. Provide the structure of the production obtained from the experiment.

4. This reaction in principle should give two regioisomers; yet, you obtain only one. Provide a concise explanation to this discrepancy based on the structure of the substituent. The amine nitrogen has a lone pair of electrons. They can be donated to the ring producing an oath and para position. In acetanilide, it’s easier to approach the par position.

5. If the starting material was phenol (also known as hydroxybenzene) instead of acetanilide and an excess of bromine was used, what product(s) would be obtained? Explain. The major product formed would be 2,4,6-tribromophenol. Since the lone pair of nitrogen in acetanilide forms a conjugation with the carbonyl group, it donates less electron density to the ring and is therefore less reactive. Bromination occurs only once in phenol, while it occurs at all three positions, both oath and para to substance....