Doreen Foy Organic chemistry lab 1 Green oxidation worksheet 1 ...
Doreen Foy Organic chemistry lab 1 1. Chemical reaction
Green oxidation worksheet
2. Reaction mechanism
3. Sublimation is used to purify volatile solids because when the vapor pressure of the solid equals the ambient pressure, the solid will sublime. It works well when the solid being sublimed is the only volatile solid in the mixture Camphor can be separated from unreacted borneol because the product used for the sublimation is “dry,” since any amount of solvent/water is removed by vacuum filtration and so upon heating the sublimation apparatus, only the camphor will sublime, leaving behind any solid borneol because borneol is a harder and less volatile solid but the separation is not an easy since they are close in volatility. Sublimation works by taking advantage of the phase changes that a substance undergoes. Therefore in sublimation, as the solid camphor volatilizes into a gas, it condenses on a cold surface (the cold finger) which is kept cold through the addition of ice. The pure product condensed on the ice finger can be scrapped off. 4. Picture of sublimation apparatus
5. My group was not successful in carrying out our sublimation and so we borrowed the melting point range from another group which was 168OC171OC. The group did not mention any difficulties in determining the melting point. 6. The IR indicated that camphor was indeed made. The expected ketone absorption peak, which is the determinant factor that the intended reaction did go to completion, was present in the spectra at 1740.92cm-1. Some other significant peaks showed up at 3405.52cm-1, 2949.88 cm-1 and 1451.76cm-1. The peak at 3405.52cm-1 is characteristic of the hydroxyl functional group, indicating the presence of either water or unreacted borneol. The other peak at 2949.88 cm-1 is characteristic of a sp3-hybridized carbon, which is present both in camphor and borneol which may suggest the presence of unreacted borneol. The peak at 1451.76cm-1 is a major peak present in a standard borneol spectrum and thus indicates the presence of unreacted borneol. 7. Which one is greener? Criteria Prevention
Green oxidation procedure Only water and hydronium ion as byproducts which are harmless
Atom economy
Smaller amount of bleach used and all reactants are used up.
Less Hazardous Chemical Synthesis
Uses acetic acid, pungent but not hazardous Camphor and all byproducts safe
Designing Safer Chemicals Safer Solvent and Auxiliaries Design for Energy Efficiency
Water as solvent which is very green Heat used only in sublimation apparatus
Use of Renewable
N/A
Jones oxidation procedure Chromium containing waste which is carcinogenic and jones reagent is harmful to environment Large amount of chromium regent used. Magnesium sulfate used as drying agent is discarded Uses concentrated sulfuric acid which is corrosive to the skin Camphor safe but chromium waste dangerous. Use of ether A lot of heat is generated and more heat is used in evaporating the ether from product Magnesium sulfate used
Feedstocks Reduce Derivatives Catalysis Design for Degradation Real –time analysis for Pollution Prevention Inherently Safer Chemistry for Accident Prevention
N/A N/A Camphor can sublime into atmosphere eventually While chlorine gas was formed, hood sash was said to be lowered No potential chemical accidents.
is discarded and not recycled N/A N/A Camphor can equally sublime into atmosphere N/A
Potential for chemical accidents with sulfuric acid Based on the chat above, it is very obvious that the reduction of borneol to camphor using household bleach and acetic acid is greener that the oxidation using the Jones reagent.
Green oxidation worksheet
2. Reaction mechanism
3. Sublimation is used to purify volatile solids because when the vapor pressure of the solid equals the ambient pressure, the solid will sublime. It works well when the solid being sublimed is the only volatile solid in the mixture Camphor can be separated from unreacted borneol because the product used for the sublimation is “dry,” since any amount of solvent/water is removed by vacuum filtration and so upon heating the sublimation apparatus, only the camphor will sublime, leaving behind any solid borneol because borneol is a harder and less volatile solid but the separation is not an easy since they are close in volatility. Sublimation works by taking advantage of the phase changes that a substance undergoes. Therefore in sublimation, as the solid camphor volatilizes into a gas, it condenses on a cold surface (the cold finger) which is kept cold through the addition of ice. The pure product condensed on the ice finger can be scrapped off. 4. Picture of sublimation apparatus
5. My group was not successful in carrying out our sublimation and so we borrowed the melting point range from another group which was 168OC171OC. The group did not mention any difficulties in determining the melting point. 6. The IR indicated that camphor was indeed made. The expected ketone absorption peak, which is the determinant factor that the intended reaction did go to completion, was present in the spectra at 1740.92cm-1. Some other significant peaks showed up at 3405.52cm-1, 2949.88 cm-1 and 1451.76cm-1. The peak at 3405.52cm-1 is characteristic of the hydroxyl functional group, indicating the presence of either water or unreacted borneol. The other peak at 2949.88 cm-1 is characteristic of a sp3-hybridized carbon, which is present both in camphor and borneol which may suggest the presence of unreacted borneol. The peak at 1451.76cm-1 is a major peak present in a standard borneol spectrum and thus indicates the presence of unreacted borneol. 7. Which one is greener? Criteria Prevention
Green oxidation procedure Only water and hydronium ion as byproducts which are harmless
Atom economy
Smaller amount of bleach used and all reactants are used up.
Less Hazardous Chemical Synthesis
Uses acetic acid, pungent but not hazardous Camphor and all byproducts safe
Designing Safer Chemicals Safer Solvent and Auxiliaries Design for Energy Efficiency
Water as solvent which is very green Heat used only in sublimation apparatus
Use of Renewable
N/A
Jones oxidation procedure Chromium containing waste which is carcinogenic and jones reagent is harmful to environment Large amount of chromium regent used. Magnesium sulfate used as drying agent is discarded Uses concentrated sulfuric acid which is corrosive to the skin Camphor safe but chromium waste dangerous. Use of ether A lot of heat is generated and more heat is used in evaporating the ether from product Magnesium sulfate used
Feedstocks Reduce Derivatives Catalysis Design for Degradation Real –time analysis for Pollution Prevention Inherently Safer Chemistry for Accident Prevention
N/A N/A Camphor can sublime into atmosphere eventually While chlorine gas was formed, hood sash was said to be lowered No potential chemical accidents.
is discarded and not recycled N/A N/A Camphor can equally sublime into atmosphere N/A
Potential for chemical accidents with sulfuric acid Based on the chat above, it is very obvious that the reduction of borneol to camphor using household bleach and acetic acid is greener that the oxidation using the Jones reagent.
