topic: atom economy · 2008. 4. 23. · the bhc synthesis of ibuprofen scheme 4, atom economy %...
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Topic: Atom EconomyA Measure of the Efficiency of a
Reaction
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Efficiency of a Reaction
• Percentage yield
Theoretical yield = (moles of limiting reagent)(stoichiometric ratio; desired product/limiting reagent)(MW of desired product)
Percentage yield= (actual yield/theoretical yield) X 100
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Equation 1a
0.08g 1.33 2.0 1.48 g (theoretical yield)0.0108mole 0.0129 0.0200 0.0108 mole (theoretical yield)
Compound 1 is the limiting reagent
Suppose the actual yield is 1.20 g of compound 4.
Percentage yield= (actual yield/theoretical yield) X 100 = (1.20 g/1.48 g) X 100 = 81%
CH3CH2CH2CH2OH NaBr H2SO4 CH3CH2CH2CH2Br NaHSO4 H2O+ + + +1 2 3 4 5 6
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Atom Economy in a Substitution Reaction
Equation 1bNa Br H2SO4 NaHSO4 H2O+ + + +CH3 CH2 CH2 CH2 OH CH3 CH2 CH2 CH2 Br
1 2 3 4 5 6
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% Atom Economy = (FW of atoms utilized/FW of all reactants) X 100 = (137/275) X 100 = 50%
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Table 4 Experimental Atom Economy of Equation 1: Based on Actual
Quantities of Reagents Used
% Experimental Atom Economy = (mass of reactants utilized in the desired product/total mass of all reactants) X 100 = (theoretical yield/total mass of all reactants) X 100 = (1.48 g/4.13 g) X 100 = 36%
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% Yield X Experimental Atom Economy
% Yield X Experimental Atom Economy = (actual yield/theoretical yield) X (mass of reactants utilized in the desired product/total mass of all reactants) X 100
%PE .EAE= (actual yield/theoretical yield) X (theoretical yield/total mass of all reactants) X 100 = (actual yield/total mass of all the reactants) X100
= (1.20 g/4.13 g) X 100 = 29%
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Atom Economy in Elimination Reactions
• Equation 2
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% Atom Economy = (FW of atoms utilized/FW of all reactants) X 100 = (56/205) X 100 = 27%
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Atom Economy in Addition Reactions
• Equation 3
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% Atom Economy = (FW of atoms utilized/FW of all reactants) X 100 = (137/137) X 100 = 100%
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Atom Economy in Rearrangement Reactions
• Equation 4
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% Atom Economy = (FW of atoms utilized/FW of all reactants) X 100 = (84/84) X 100 = 100%
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Scheme 1 Atom Economy in The Clorohydrin Route to
Ethylene Oxide
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% Atom Economy = (FW of atoms utilized/FW of all reactants) X 100 = (44/189) X 100 = 23%
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Scheme 2 Atom Economy in The Catalytic Route to
Ethylene Oxide
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% Atom Economy = (FW of atoms utilized/FW of all reactants) X 100 = (44/44) X 100 = 100%
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The Boots Synthesis of IbuprofenScheme 3, Atom Economy
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% Atom Economy = (FW of atoms utilized/FW of all reactants) X 100 = (206/514.5) X 100 = 40%
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The BHC Synthesis of Ibuprofen Scheme 4, Atom Economy
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% Atom Economy = (FW of atoms utilized/FW of all reactants) X 100 = (206/266) X 100 = 77%