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- https://chem.libretexts.org/Courses/Oregon_Institute_of_Technology/OIT%3A_CHE_332_--_Organic_Chemistry_II_(Lund)/11%3A_Nucleophilic_Acyl_Substitution_Reactions/11.1%3A_Carboxylic_Acid_DerivativesThe functional groups at the heart of this chapter are called carboxylic acid derivatives: they include carboxylic acids themselves, carboxylates (deprotonated carboxylic acids), amides, esters, thioe...The functional groups at the heart of this chapter are called carboxylic acid derivatives: they include carboxylic acids themselves, carboxylates (deprotonated carboxylic acids), amides, esters, thioesters, and acyl phosphates.
- https://chem.libretexts.org/Courses/Oregon_Institute_of_Technology/OIT%3A_CHE_333_-_Organic_Chemistry_III_(Lund)/New_Page/11%3A_Nucleophilic_Acyl_Substitution_Reactions/11.1%3A_Carboxylic_Acid_DerivativesThe functional groups at the heart of this chapter are called carboxylic acid derivatives: they include carboxylic acids themselves, carboxylates (deprotonated carboxylic acids), amides, esters, thioe...The functional groups at the heart of this chapter are called carboxylic acid derivatives: they include carboxylic acids themselves, carboxylates (deprotonated carboxylic acids), amides, esters, thioesters, and acyl phosphates.
- https://chem.libretexts.org/Courses/Oregon_Institute_of_Technology/OIT_(Lund)%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)/11%3A_Nucleophilic_Acyl_Substitution_Reactions/11.09%3A_Nucleophilic_Acyl_Substitution_Reactions_in_the_LaboratoryAll of the biological nucleophilic acyl substitution reactions we have seen so far have counterparts in laboratory organic synthesis. Mechanistically, one of the biggest differences between the biolog...All of the biological nucleophilic acyl substitution reactions we have seen so far have counterparts in laboratory organic synthesis. Mechanistically, one of the biggest differences between the biological and the lab versions is that the lab reactions usually are run with a strong acid or base as a catalyst, whereas biological reactions are of course taking place at physiological pH.
- https://chem.libretexts.org/Courses/SUNY_Oneonta/Chem_322_Lecture_Content/06%3A_Nucleophilic_Acyl_Substitution_Reactions/6.07%3A_Hydrolysis_of_Thioesters_Esters_and_AmidesSo far we have been looking at the formation of thioesters, carboxylic esters, and amides, starting from carboxylates. In hydrolytic acyl substitution reactions, nucleophilic water is the incoming nuc...So far we have been looking at the formation of thioesters, carboxylic esters, and amides, starting from carboxylates. In hydrolytic acyl substitution reactions, nucleophilic water is the incoming nucleophile and a carboxylate group is the final product. Because carboxylates are the least reactive among the carboxylic acid derivatives, these hydrolysis reactions are thermodynamically favorable, with thioester hydrolysis the most favorable of the three.
- https://chem.libretexts.org/Courses/Martin_Luther_College/Organic_Chemistry_-_MLC/04%3A_Carbonyls/4.02%3A_Carboxylic_Acids/4.2.05%3A_Chemistry_of_EstersIn the first two steps of the mechanism, the OR leaving group from the ester is replaced by the R group from the Grignard reagent through a nucleophilic acyl substitution. 2) Draw the product of the r...In the first two steps of the mechanism, the OR leaving group from the ester is replaced by the R group from the Grignard reagent through a nucleophilic acyl substitution. 2) Draw the product of the reaction between the following molecule and LiAlH 4 , and the product of the reaction between the following molecule and DIBAL.
- https://chem.libretexts.org/Courses/SUNY_Oneonta/Organic_Chemistry_with_a_Biological_Emphasis_(SUNY_Oneonta)/11%3A_Nucleophilic_Acyl_Substitution_Reactions/11.10%3A_Nucleophilic_Acyl_Substitution_Reactions_in_the_LaboratoryAll of the biological nucleophilic acyl substitution reactions we have seen so far have counterparts in laboratory organic synthesis. Mechanistically, one of the biggest differences between the biolog...All of the biological nucleophilic acyl substitution reactions we have seen so far have counterparts in laboratory organic synthesis. Mechanistically, one of the biggest differences between the biological and the lab versions is that the lab reactions usually are run with a strong acid or base as a catalyst, whereas biological reactions are of course taking place at physiological pH.
- https://chem.libretexts.org/Courses/Smith_College/CHM_222_Chemistry_II%3A_Organic_Chemistry_(2025)/12%3A_Carboxylic_Acid_Derivatives-_Nucleophilic_Acyl_Substitution_Reactions/12.07%3A_Chemistry_of_EstersIn the first two steps of the mechanism, the OR leaving group from the ester is replaced by the R group from the Grignard reagent through a nucleophilic acyl substitution. 2) Draw the product of the r...In the first two steps of the mechanism, the OR leaving group from the ester is replaced by the R group from the Grignard reagent through a nucleophilic acyl substitution. 2) Draw the product of the reaction between the following molecule and LiAlH 4 , and the product of the reaction between the following molecule and DIBAL.
- https://chem.libretexts.org/Courses/SUNY_Oneonta/Organic_Chemistry_with_a_Biological_Emphasis_(SUNY_Oneonta)/11%3A_Nucleophilic_Acyl_Substitution_Reactions/11.02%3A_Carboxylic_Acid_DerivativesThe functional groups at the heart of this chapter are called carboxylic acid derivatives: they include carboxylic acids themselves, carboxylates (deprotonated carboxylic acids), amides, esters, thioe...The functional groups at the heart of this chapter are called carboxylic acid derivatives: they include carboxylic acids themselves, carboxylates (deprotonated carboxylic acids), amides, esters, thioesters, and acyl phosphates.
- https://chem.libretexts.org/Courses/SUNY_Oneonta/Chem_322_Lecture_Content/06%3A_Nucleophilic_Acyl_Substitution_Reactions/6.06%3A_Acyl_PhosphatesThioesters, which are themselves quite reactive in acyl substitution reactions (but less so than acyl phosphates), play a crucial role in the metabolism of fatty acids The ‘acyl X group’ in a thioeste...Thioesters, which are themselves quite reactive in acyl substitution reactions (but less so than acyl phosphates), play a crucial role in the metabolism of fatty acids The ‘acyl X group’ in a thioester is a thiol.
- https://chem.libretexts.org/Courses/Oregon_Institute_of_Technology/OIT_(Lund)%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)/11%3A_Nucleophilic_Acyl_Substitution_Reactions/11.05%3A_Acyl_PhosphatesThioesters, which are themselves quite reactive in acyl substitution reactions (but less so than acyl phosphates), play a crucial role in the metabolism of fatty acids The ‘acyl X group’ in a thioeste...Thioesters, which are themselves quite reactive in acyl substitution reactions (but less so than acyl phosphates), play a crucial role in the metabolism of fatty acids The ‘acyl X group’ in a thioester is a thiol.
- https://chem.libretexts.org/Courses/Matanuska-Susitna_College/MatSu_College-CHEM_A104_Introduction_to_Organic_and_Biochemistry/15%3A_Organic_Acids_and_Bases_and_Some_of_Their_Derivatives/15.07%3A_Physical_Properties_of_EstersEsters have polar bonds but do not engage in hydrogen bonding and are therefore intermediate in boiling points between the nonpolar alkanes and the alcohols, which engage in hydrogen bonding. Ester mo...Esters have polar bonds but do not engage in hydrogen bonding and are therefore intermediate in boiling points between the nonpolar alkanes and the alcohols, which engage in hydrogen bonding. Ester molecules can engage in hydrogen bonding with water, so esters of low molar mass are therefore somewhat soluble in water.
