Note that ammonia gas is produced during the reaction and usually can be detected during the reflux of the benzonitrile with the sodium hydroxide solution
Purpose: To create benzoic acid by hydrolyzing a nitrile in basic and acidic conditions and to compare if the reaction is a better reaction than the Grignard reaction.
Chem Rxn is …
Background: Another way to make benzoic acid with amine involved is hydrolyzing a nitrile. Hydrolysis of Nitriles can occur under acidic and/or basic condition. In this reaction the basic condition would make the benzonitirle turn into an amide and the acidic condition would turn the amide into benzoic acid. The first part of the reaction is to heat the nitrile with sodium hydroxide under refluxation. The hydroxide group would add to the benzonitirle with heat as a catalyst. Then during refluxing the nitrogen would protonate from the water and make it more electrophilic and after rearrangements and deprotonations ammonia gas will be released because it will become a good leaving group. In the acidic condition, the reaction has be under cool temps when acid is being added. The oxygen is protonated from the hydrochloride and becomes benzoic acid.
Methods: IR spectra, recrystallization, melting point, vacuum filtration, refluxing.
MSDS:
Benzonitrile
Molecular Weight: 103.12 g/mole
oiling Point: 190.7°C
Melting Point: -12.8°C
Solubility: Insoluble in cold water.
Combustible. Keep away from heat. Keep away from sources of ignition.
Very hazardous in case of eye contact (irritant). Hazardous in case of skin contact
density?: ?1.0 g/ml
Benzoic Acid
Molecular Weight: 122.12 g/mole
Boiling Point: 249.2°C
Melting Point: 122.4°C
Solubility: Very slightly soluble in cold water
May be combustible at high temperature.
Keep away from heat. Keep away from sources of ignition.
Keep container tightly closed. Keep container in a cool, well-ventilated area.
Hazardous in case of skin contact (irritant), of eye contact (irritant), of ingestion, of inhalation
1.08 g/mL
Hydrochloric acid
36.46 g/mol
Boiling Point: 108.58 C
Melting Point: -62.25°C
Solubility: Soluble in cold water, hot water, diethyl ethe
Non-flammable.
Very hazardous in case of skin contact (corrosive, irritant, permeator), of eye contact (ir
Keep locked up.. Keep container dry. Do not ingest.
r tightly closed. Keep container in a cool, well-ventilated area.
Density?: ?1.2 g/mL at 25 °C
Diethyl ether
Molecular Weight: 74.12g/mole
Boiling Point: 34.6°C
Melting Point: -116.3°C
Soluble in acetone. Partially soluble in cold water
: Flammable.
Hazardous in case of skin contact (irritant), of eye contact (irritant), of ingestion, of inhalation.
Keep away from heat. Keep away from sources of ignition.
Keep container in a cool, well-ventilated area. Keep container tightly closed
0.706 g/mL at 25 °C
Sodium Hydroxide
NaOH
Melting Point: 323°C
Boiling Point: 1388°C
Solubility: Easily soluble in cold water.
Molecular Weight: 40 g/mole
Density: 2.13
Non-flammable.
Very hazardous in case of skin contact (corrosive, irritant, permeator), of eye contact (irritant, corrosive), of ingestion, of inhalation.
Keep container dry. Do not breathe dust. Never add water to this product.
DI water
H2O
Boiling Point: 100°C (
Molecular Weight: 18.02 g/mole
Melt : 0°C
Density 1 g/cm3
Non-corrosive
STOPPP
Magnesium
Molecular Weight: 24.31 g/mole
Boiling Point: 1100°C
Melting Point: 651°C (
Very slightly soluble in hot water. Insoluble in cold water. Insoluble in chromium trioxides, and mineral acids, alkalies.
Slightly hazardous in case of skin contact (irritant), of eye contact (irritant), of ingestion, of inhalation
Flammable.
Keep container in a cool, well-ventilated area. Keep container tightly closed and sealed until ready for us
1.738 g/cm³
Iodine
Molecular Weight: 253.81 g/mole
Boiling Point: 184.4°C
Melting Point: 113.7°C
Easily soluble in diethyl ether. Soluble in methanol. Very slightly soluble in cold water, hot water
Non-flammable.
Very hazardous in case of skin contact (irritant), of eye contact (irritant), of ingestion, of inhalation.
Keep container dry. Do not ingest. Do not breathe dust. Never add water to this product. In
4.94g/mL
Benzoate salt
Molecular Weight: 144.11 g/mole
Melting Point: >300°C (572°F
Solubility: Easily soluble in cold water, hot water.
May be combustible at high temperature.
Hazardous in case of skin contact (irritant), of eye contact (irritant), of inhalation.
Keep locked up.. Keep away from heat. Keep away from sources of ignition.
: Keep container tightly closed. Keep container in a cool, well-ventilated area. H
Density?: ?1.497 g/cm3
Bromobenzene
1.5g/ml
Molecular Weight: 157.02 g/mole
Boiling Point: 156.2°C
Melting Point: -30.6°C
Soluble in methanol, diethyl ether. Very slightly soluble in cold water.
Flammable.
Keep away from heat. Keep away from sources of ignition.
Store in a segregated and approved area. Keep container in a cool, well-ventilated area
ethyl acetate
Molecular Weight: 88.11 g/mole
Boiling Point: 77°C (170.6°F)
Melting Point: -83°C (-117.4°F)
Solubility: Soluble in cold water, hot water, diethyl ether, acetone, alcohol, benzene.
Flammable
Hazardous in case of ingestion, of inhalation. S
Store in a segregated and approved area. Keep container in a cool, well-ventilated area.
maleic anhydride
Molecular Weight: 98.06 g/mole
Boiling Point: 202°C
Melting Point: 52.8°C
Soluble in cold water, hot water. Very slightly soluble in methanol.
Very hazardous in case of ingestion. Hazardous in case of skin contact
Keep container dry. Keep away from heat
Keep container dry. Keep in a cool plac
May be combustible at high temperature.
Density: 1.48 g/cm³
Cyclopentadiene
Molecular Weight?: ?66.103 g/mol
Boiling 41.5-42.0°C
Melting -95.54 deg C
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist
Store in cool place. Keep container tightly closed in a dry and well-ventilated place
Density 0.93 g/cm3
Flammable liquid and vapour. H302 Harmful if swallowed.
Ligroin
Mass 82.2 g/mol
Melting point
