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By properties I mean the +I or -I effect as compared to other functional groups along with whether it induces a +R or -R effect?
Thank you. :DAdityaDev said:COOR is an electron withdrawing group. But I don't think it shows resonance due to O-R bond.
It is a weaker +I group than COOH and SO3H
Thank you. :)lavoisier said:I think I was taught COOR was a meta-directing group in electrophylic substitutions on Ar-COOR; and alpha-beta unsaturated esters do undergo addition in beta.
So in theory it does have a 'resonance' effect. Not because of the O-R bond, but because of the C=O bond.
The -COOR functional group is composed of a carbonyl group (-C=O) bonded to an alkyl or aryl group (-R) and a single bonded oxygen (-O). This functional group is commonly found in esters, which are organic compounds formed by the reaction of an alcohol and a carboxylic acid.
Compounds containing the -COOR functional group tend to have low boiling points, are generally insoluble in water, and have distinct odors. They also exhibit polar properties due to the presence of the carbonyl group, making them capable of forming hydrogen bonds with other molecules.
The -COOR functional group is prone to hydrolysis, meaning it can be broken down by water. This reaction produces a carboxylic acid and an alcohol. Additionally, esters can undergo transesterification, a reaction in which the -COOR group is replaced with another alcohol, and saponification, a reaction in which the -COOR group is cleaved by a strong base to form a carboxylate salt and an alcohol.
The -COOR functional group is electron-withdrawing, meaning it can pull electrons away from neighboring atoms. This results in a more polar and reactive compound, as the carbonyl group can act as an electrophile in nucleophilic substitution reactions. The presence of the -COOR group also makes a compound more susceptible to hydrolysis and other reactions mentioned above.
Compounds with the -COOR functional group are commonly used as flavorings and fragrances in the food and cosmetic industries. They are also used as solvents, plasticizers, and in the production of pharmaceuticals. In addition, esters are important intermediates in the production of other organic compounds.