nitration of acetanilide
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 procedure:
The experimental procedure was conducted as per instructions from the chemistry 220 manual. We were told to add 5grams of Acetanilide but due to time constraints I had added 5.05grams. Whilst preparing the mixture of Nitric acid and sulphuric acid, I misjudged the reading on the measuring cylinder once again due to time constraints and consideration toward my fellow peers. As indicated, we were instructed to add the mixture drop wise; I had allowed the tap to run due to a confusion of the tap mechanism. The mixture therefore went up to 20 degrees and dropped gradually back to 11 degrees .After adding a little over 45mL of methanol, in order to start the process of recrystallization, my product was still cloudy. I feel I therefore may have added too much to re-dissolve the product. It took time for my product to break down over the steam and dissolve, yet eventually, suggested by the demonstrator I left it to become fully crystalized once again therefore becoming a ice cold slurry. Thereafter filtration took place.
Reaction Mechanism:
Reference:www.kshitj-school.com & en.wikipedia.org
Melting point of substance prepared:
Para-nitroacetanilide= 214-217 degrees Celsius(http://content.hccfl.edu/faculty/bertrubini/2211%20-%20Electrophilic%20Aromatic%20Substitution.pdf)
Melting point of substance prepared:
Expected yield:
Calculation of yield
Limiting agent –acetanilide
Moles for limiting agent=5.05g/135.16g/mol=0.0374mol
Moles
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 procedure:
The experimental procedure was conducted as per instructions from the chemistry 220 manual. We were told to add 5grams of Acetanilide but due to time constraints I had added 5.05grams. Whilst preparing the mixture of Nitric acid and sulphuric acid, I misjudged the reading on the measuring cylinder once again due to time constraints and consideration toward my fellow peers. As indicated, we were instructed to add the mixture drop wise; I had allowed the tap to run due to a confusion of the tap mechanism. The mixture therefore went up to 20 degrees and dropped gradually back to 11 degrees .After adding a little over 45mL of methanol, in order to start the process of recrystallization, my product was still cloudy. I feel I therefore may have added too much to re-dissolve the product. It took time for my product to break down over the steam and dissolve, yet eventually, suggested by the demonstrator I left it to become fully crystalized once again therefore becoming a ice cold slurry. Thereafter filtration took place.
Reaction Mechanism:
Reference:www.kshitj-school.com & en.wikipedia.org
Melting point of substance prepared:
Para-nitroacetanilide= 214-217 degrees Celsius(http://content.hccfl.edu/faculty/bertrubini/2211%20-%20Electrophilic%20Aromatic%20Substitution.pdf)
Melting point of substance prepared:
Expected yield:
Calculation of yield
Limiting agent –acetanilide
Moles for limiting agent=5.05g/135.16g/mol=0.0374mol
Moles