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<div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Resonance stabilization of the carboxylate ion</span> </div> </a> <ul id="toc-Resonance_stabilization_of_the_carboxylate_ion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Alkyation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alkyation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Alkyation</span> </div> </a> <ul id="toc-Alkyation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nucleophilic_substitution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nucleophilic_substitution"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Nucleophilic substitution</span> </div> </a> <ul id="toc-Nucleophilic_substitution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Reduction</span> </div> </a> <ul id="toc-Reduction-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Examples" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Examples"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Examples</span> 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical group (RCOO); conjugate base of a carboxylic acid</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Carboxylate-resonance-hybrid.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Carboxylate-resonance-hybrid.png/255px-Carboxylate-resonance-hybrid.png" decoding="async" width="255" height="235" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Carboxylate-resonance-hybrid.png/383px-Carboxylate-resonance-hybrid.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Carboxylate-resonance-hybrid.png/510px-Carboxylate-resonance-hybrid.png 2x" data-file-width="806" data-file-height="742" /></a><figcaption>Carboxylate ion</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Acrylate-ion-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Acrylate-ion-3D-balls.png/220px-Acrylate-ion-3D-balls.png" decoding="async" width="220" height="166" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Acrylate-ion-3D-balls.png/330px-Acrylate-ion-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Acrylate-ion-3D-balls.png/440px-Acrylate-ion-3D-balls.png 2x" data-file-width="1021" data-file-height="771" /></a><figcaption>Acrylate ion</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>carboxylate</b> is the <a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">conjugate base</a> of a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>, <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">RCOO<sup class="template-chem2-sup">−</sup></span> (or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<span class="template-chem2-su"><span>−</span><span>2</span></span></span>). It is an <a href="/wiki/Ion#anion" title="Ion"> anion</a>, an <a href="/wiki/Ion" title="Ion">ion</a> with <a href="/wiki/Negative_charge" class="mw-redirect" title="Negative charge">negative charge</a>. </p><p><b>Carboxylate salts</b> are <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> that have the general formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">M(RCOO)<sub class="template-chem2-sub"><i>n</i></sub></span>, where M is a metal and <i>n</i> is 1, 2,.... <b>Carboxylate esters</b> have the general formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCOOR′</span> (also written as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>R′</span>), where R and R′ are organic groups. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylate&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylate ions can be formed by deprotonation of carboxylic acids. Such acids typically have <a href="/wiki/PKa" class="mw-redirect" title="PKa">p<i>K</i><sub>a</sub></a> of less than 5, meaning that they can be deprotonated by many bases, such as <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> or <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a>.<sup id="cite_ref-March4_1-0" class="reference"><a href="#cite_note-March4-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 271–2">: 271–2 </span></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RCOOH + NaOH -> RCOONa + H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>RCOOH</mtext> <mo>+</mo> <mtext>NaOH</mtext> <mo stretchy="false">⟶</mo> <mtext>RCOONa</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RCOOH + NaOH -> RCOONa + H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/7fb2733412e9d784acbd538a646c4690cdf1c25e" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:40.497ex; height:2.843ex;" alt="{\displaystyle {\ce {RCOOH + NaOH -> RCOONa + H2O}}}"></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Resonance_stabilization_of_the_carboxylate_ion">Resonance stabilization of the carboxylate ion</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylate&action=edit&section=2" title="Edit section: Resonance stabilization of the carboxylate ion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acids easily dissociate into a carboxylate anion and a positively charged hydrogen ion (proton), much more readily than alcohols do (into an <a href="/wiki/Alkoxide" title="Alkoxide">alkoxide</a> ion and a proton), because the carboxylate ion is stabilized by <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance</a>. The negative charge that is left after <a href="/wiki/Deprotonation" title="Deprotonation">deprotonation</a> of the carboxyl group is delocalized between the two <a href="/wiki/Electronegative" class="mw-redirect" title="Electronegative">electronegative</a> oxygen atoms in a resonance structure. If the R group is an electron-withdrawing group (such as <a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">–CF<sub>3</sub></a>), the basicity of the carboxylate will be further weakened.<sup id="cite_ref-March4_1-1" class="reference"><a href="#cite_note-March4-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 264–5">: 264–5 </span></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Carboxylate-resonance-2D.png" class="mw-file-description" title="Equivalence of the resonance forms the delocalised form of a general carboxylate anion"><img alt="Equivalence of the resonance forms the delocalised form of a general carboxylate anion" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Carboxylate-resonance-2D.png/400px-Carboxylate-resonance-2D.png" decoding="async" width="400" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Carboxylate-resonance-2D.png/600px-Carboxylate-resonance-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/Carboxylate-resonance-2D.png/800px-Carboxylate-resonance-2D.png 2x" data-file-width="2100" data-file-height="423" /></a></span></dd></dl> <p>This <a href="/wiki/Delocalization" class="mw-redirect" title="Delocalization">delocalization</a> of the electron means that both of the oxygen atoms are less strongly negatively charged: the positive proton is therefore less strongly attracted back to the carboxylate group once it has left; hence, the carboxylate ion is more stable and less basic as a result of <a href="/wiki/Resonance_stabilization" class="mw-redirect" title="Resonance stabilization">resonance stabilization</a> of the negative charge. In contrast, an <a href="/wiki/Alkoxide" title="Alkoxide">alkoxide</a> ion, once formed, would have a strong negative charge localized on its lone oxygen atom, which would strongly attract any nearby protons (indeed, alkoxides are very strong bases). Because of resonance stabilization, carboxylic acids have much lower <a href="/wiki/PKa" class="mw-redirect" title="PKa">p<i>K</i><sub>a</sub></a> values (and are therefore stronger acids) than <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a>. For example, the p<i>K</i><sub>a</sub> value of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> is 4.8, while <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> has a p<i>K</i><sub>a</sub> of 16. Hence acetic acid is a much stronger acid than ethanol. This in turn means that for equimolar solutions of a carboxylic acid or an alcohol in water, the carboxylic acid would have a much lower <a href="/wiki/PH" title="PH">pH</a>.<sup id="cite_ref-March4_1-2" class="reference"><a href="#cite_note-March4-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 263–7">: 263–7 </span></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylate&action=edit&section=3" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Alkyation">Alkyation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylate&action=edit&section=4" title="Edit section: Alkyation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acid salts with a hydrogen atom in the <i>alpha</i> position next to the carboxylate group can be converted to <a href="/wiki/Dianion" title="Dianion">dianions</a> with strong bases like <a href="/wiki/Lithium_diisopropylamide" title="Lithium diisopropylamide">lithium diisopropylamide</a>. These react with <a href="/wiki/Alkyl_halides" class="mw-redirect" title="Alkyl halides">alkyl halides</a> to give derivatives:<sup id="cite_ref-March4_1-3" class="reference"><a href="#cite_note-March4-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 474">: 474 </span></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCH<sub class="template-chem2-sub">2</sub>COO<sup class="template-chem2-sup">−</sup> + Li<sup class="template-chem2-sup">+</sup>[<sup class="template-chem2-sup">−</sup>N(CH(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub>] → RCH<sup class="template-chem2-sup">−</sup>COO<sup class="template-chem2-sup">−</sup></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCH<sup class="template-chem2-sup">−</sup>COO<sup class="template-chem2-sup">−</sup> + R'X → RR'CHCOO<sup class="template-chem2-sup">−</sup> + X<sup class="template-chem2-sup">−</sup></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Nucleophilic_substitution">Nucleophilic substitution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylate&action=edit&section=5" title="Edit section: Nucleophilic substitution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylate ions are good <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a>. They react with <a href="/wiki/Alkyl_halides" class="mw-redirect" title="Alkyl halides">alkyl halides</a> to form <a href="/wiki/Ester" title="Ester">esters</a>. The following reaction shows the reaction mechanism.<sup id="cite_ref-March4_1-4" class="reference"><a href="#cite_note-March4-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 398–9">: 398–9 </span></sup> </p> <figure class="mw-halign-none" typeof="mw:File/Thumb"><a href="/wiki/File:Ester-from-carboxylate-and-alkyl-halide-2D-skeletal.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Ester-from-carboxylate-and-alkyl-halide-2D-skeletal.png/600px-Ester-from-carboxylate-and-alkyl-halide-2D-skeletal.png" decoding="async" width="600" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Ester-from-carboxylate-and-alkyl-halide-2D-skeletal.png/900px-Ester-from-carboxylate-and-alkyl-halide-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Ester-from-carboxylate-and-alkyl-halide-2D-skeletal.png/1200px-Ester-from-carboxylate-and-alkyl-halide-2D-skeletal.png 2x" data-file-width="2100" data-file-height="297" /></a><figcaption>The <a href="/wiki/SN2_reaction" title="SN2 reaction">S<sub>N</sub>2 reaction</a> between <a href="/wiki/Sodium_acetate" title="Sodium acetate">sodium acetate</a> and <a href="/wiki/Bromoethane" title="Bromoethane">bromoethane</a>. The products are <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a> and <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>.</figcaption></figure> <p>The nucleophilicity of carboxylate ions is much weaker than that of <a href="/wiki/Hydroxide" title="Hydroxide">hydroxide</a> and <a href="/wiki/Alkoxide" title="Alkoxide">alkoxide</a> ions, but stronger than that of <a href="/wiki/Halide" title="Halide">halide</a> anions (in a <a href="/wiki/Polar_aprotic_solvent" title="Polar aprotic solvent">polar aprotic solvent</a>, though there are other effects such as <a href="/wiki/Solubility" title="Solubility">solubility</a> of the ion). </p> <div class="mw-heading mw-heading3"><h3 id="Reduction">Reduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylate&action=edit&section=6" title="Edit section: Reduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Unlike the reduction of ester, the reduction of carboxylate is different, due to the lack of the <a href="/wiki/Leaving_group" title="Leaving group">leaving group</a> and the relatively electron-rich carbon atom (due to the negative charge on the oxygen atoms). With a small amount of acid, the reaction occurs with <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a> by changing the LAH into the <a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis acid</a> <a href="/wiki/Aluminium_hydride" title="Aluminium hydride">AlH<sub>3</sub></a> in the process, converting the oxyanion to 4 Al–O bonds.<sup id="cite_ref-March4_1-5" class="reference"><a href="#cite_note-March4-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1212">: 1212 </span></sup> </p><p><span typeof="mw:File"><a href="/wiki/File:Reaction_of_carboxylic_acids_reduction_-_part_two.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Reaction_of_carboxylic_acids_reduction_-_part_two.svg/750px-Reaction_of_carboxylic_acids_reduction_-_part_two.svg.png" decoding="async" width="750" height="124" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Reaction_of_carboxylic_acids_reduction_-_part_two.svg/1125px-Reaction_of_carboxylic_acids_reduction_-_part_two.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/Reaction_of_carboxylic_acids_reduction_-_part_two.svg/1500px-Reaction_of_carboxylic_acids_reduction_-_part_two.svg.png 2x" data-file-width="3354" data-file-height="555" /></a></span> <span typeof="mw:File/Frameless"><a href="/wiki/File:Reaction_of_carboxylic_acids_reduction_-_part_three.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Reaction_of_carboxylic_acids_reduction_-_part_three.svg/700px-Reaction_of_carboxylic_acids_reduction_-_part_three.svg.png" decoding="async" width="700" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Reaction_of_carboxylic_acids_reduction_-_part_three.svg/1050px-Reaction_of_carboxylic_acids_reduction_-_part_three.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Reaction_of_carboxylic_acids_reduction_-_part_three.svg/1400px-Reaction_of_carboxylic_acids_reduction_-_part_three.svg.png 2x" data-file-width="512" data-file-height="101" /></a></span> </p> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylate&action=edit&section=7" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This list is for cases where there is a separate article for the anion or its derivatives. All other organic acids should be found at their parent carboxylic acid. </p> <ul><li><a href="/wiki/Formate" title="Formate">Formate</a> ion, HCOO<sup>−</sup></li> <li><a href="/wiki/Acetate" title="Acetate">Acetate</a> ion, CH<sub>3</sub>COO<sup>−</sup></li> <li><a href="/wiki/Methanetetracarboxylate" title="Methanetetracarboxylate">Methanetetracarboxylate</a> ion, C(COO<sup>−</sup>)<sub>4</sub></li> <li><a href="/wiki/Oxalate" title="Oxalate">Oxalate</a> ion, <span class="chemf nowrap">(COO)<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylate&action=edit&section=8" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxylic acid</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylate&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-March4-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-March4_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-March4_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-March4_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-March4_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-March4_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-March4_1-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMarch,_Jerry1992" class="citation cs2"><a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (1992), <i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i> (4th ed.), New York: Wiley, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-60180-2" title="Special:BookSources/0-471-60180-2"><bdi>0-471-60180-2</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.edition=4th&rft.pub=Wiley&rft.date=1992&rft.isbn=0-471-60180-2&rft.au=March%2C+Jerry&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylate" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Carboxylate&oldid=1241025863">https://en.wikipedia.org/w/index.php?title=Carboxylate&oldid=1241025863</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a 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