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What factors may influence the yield of an ester?
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Michael Flynn
What factors may influence the yield of an ester?
It is possible to simply heat up a carboxylic acid with an alcohol to produce an ester by elimination of water; but often there are other functional groups that are either sensitive to the reaction conditions; or provide competing products.
Frequently,esters are made by reacting an acid halide (R - CO-X); where X is Br or Cl; with an alcohol.
The -OH of the alcohol engages in nucleophilic attack on the carbonyl bearing the halogen. The yield may be reduced if there are other attacking groups on the alcohol; (such as another -OH or -NH2 group) or other leaving groups besides the halogen elsewhere on the acid chloride (such as toluene sulfonate,other halogens,or phosphate).
The basic idea is; you want to set up your reaction to minimize competing products that will waste your starting material .
It is possible to simply heat up a carboxylic acid with an alcohol to produce an ester by elimination of water; but often there are other functional groups that are either sensitive to the reaction conditions; or provide competing products.
Frequently,esters are made by reacting an acid halide (R - CO-X); where X is Br or Cl; with an alcohol.
The -OH of the alcohol engages in nucleophilic attack on the carbonyl bearing the halogen. The yield may be reduced if there are other attacking groups on the alcohol; (such as another -OH or -NH2 group) or other leaving groups besides the halogen elsewhere on the acid chloride (such as toluene sulfonate,other halogens,or phosphate).
The basic idea is; you want to set up your reaction to minimize competing products that will waste your starting material .
There are several factors and dependent on specific reactant, but for general, these factors listed below should be noticed.
First is the chemical properties of the reactants. Take that an alcohol and an acid dehydrate to form a ester for example, the condition is acidic solution as usually do. The figure below shows a general mechanism of ester formation under acidic condition.
There are several factors and dependent on specific reactant, but for general, these factors listed below should be noticed.
First is the chemical properties of the reactants. Take that an alcohol and an acid dehydrate to form a ester for example, the condition is acidic solution as usually do. The figure below shows a general mechanism of ester formation under acidic condition.
It is possible to simply heat up a carboxylic acid with an alcohol to produce an ester by elimination of water; but often there are other functional groups that are either sensitive to the reaction conditions; or provide competing products.
Frequently,esters are made by reacting an acid halide (R - CO-X); where X is Br or Cl; with an alcohol.
The -OH of the alcohol engages in nucleophilic attack on the carbonyl bearing the halogen. The yield may be reduced if there are other attacking groups on the alcohol; (such as another -OH or -NH2 group) or other leaving groups besides the halogen elsewhere on the acid chloride (such as toluene sulfonate,other halogens,or phosphate).
The basic idea is; you want to set up your reaction to minimize competing products that will waste your starting material .
It is possible to simply heat up a carboxylic acid with an alcohol to produce an ester by elimination of water; but often there are other functional groups that are either sensitive to the reaction conditions; or provide competing products.
Frequently,esters are made by reacting an acid halide (R - CO-X); where X is Br or Cl; with an alcohol.
The -OH of the alcohol engages in nucleophilic attack on the carbonyl bearing the halogen. The yield may be reduced if there are other attacking groups on the alcohol; (such as another -OH or -NH2 group) or other leaving groups besides the halogen elsewhere on the acid chloride (such as toluene sulfonate,other halogens,or phosphate).
The basic idea is; you want to set up your reaction to minimize competing products that will waste your starting material .
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There are several factors and dependent on specific reactant, but for general, these factors listed below should be noticed.
First is the chemical properties of the reactants. Take that an alcohol and an acid dehydrate to form a ester for example, the condition is acidic solution as usually do. The figure below shows a general mechanism of ester formation under acidic condition.
There are several factors and dependent on specific reactant, but for general, these factors listed below should be noticed.
First is the chemical properties of the reactants. Take that an alcohol and an acid dehydrate to form a ester for example, the condition is acidic solution as usually do. The figure below shows a general mechanism of ester formation under acidic condition.
More
VOTE