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Organic redox reaction
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<h2 id="organic-oxidations">Organic oxidations</h2> <p>Most oxidations are conducted with air or <a href="/facts/Oxygen/acyn6o8r">oxygen</a>, especially in industry. These oxidation include routes to chemical compounds, remediation of pollutants, and <a href="/facts/Combustion/ohQoWj8z">combustion</a>. Some commercially important oxidations are listed: </p> Industrial oxidations of organic compounds<table><tbody><tr><th>product</th><th>scale (millions of tons/year in 1990's)<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a></th></tr><tr><td><a href="/facts/Terephthalic_acid/ClRNc6m0">terephthalic acid</a> and esters</td><td>15</td></tr><tr><td><a href="/facts/Cumylhydroperoxide/A5mB6LIW">cumylhydroperoxide</a></td><td>6.5</td></tr><tr><td><a href="/facts/Benzoic_acid/7HrmrBYS">benzoic acid</a></td><td>0.28</td></tr><tr><td><a href="/facts/Adipic_acid/8l8ahlDC">adipic acid</a></td><td>2.2</td></tr><tr><td><a href="/facts/Propylene_oxide/XWz8SU72">propylene oxide</a></td><td>4</td></tr><tr><td><a href="/facts/Adipic_acid/8l8ahlDC">adipic acid</a></td><td>2.2</td></tr></tbody></table> <p>Many reagents have been invented for organic oxidations. Organic oxidations reagents are usually classified according to the functional group attacked by the oxidant: </p> <ul><li>Oxidation of C-H bonds:</li></ul> R3CH + O → R3COH R2CH2 + O → R2CH(OH) R2CH(OH) + O → R2CO + H2O RCH3 + O → RCH2(OH) RCH2(OH) + O → RCHO + H2O RCHO + O → RCO2H <ul><li>Oxidation of C-C, C=C, and C≡C bonds</li> <li>Oxidation of alcohols and various carbonyls</li></ul> <p>Often the substrate to be oxidized features more than one functional group. In such cases, selective oxidations become important. </p> <h2 id="organic-reductions">Organic reductions</h2> <p>In organic chemistry, reduction is equivalent to the addition of hydrogen atoms, usually in pairs. The reaction of unsaturated organic compounds with hydrogen gas is called <a href="/facts/Hydrogenation/l7EzNSA7">hydrogenation</a>. The reaction of saturated organic compounds with hydrogen gas is called <a href="/facts/Hydrogenolysis/v8VT0Bx2">hydrogenolysis</a>. Hydrogenolyses necessarily cleaves C-X bonds (X = C, O, N, etc.). Reductions can also be effected by adding hydride and proton sources, the so-called heterolytic pathway. Such reactions are often effected using stoichiometric hydride reagents such as <a href="/facts/Sodium_borohydride/D2Hwts5x">sodium borohydride</a> or <a href="/facts/Lithium_aluminium_hydride/QMMhdqEy">lithium aluminium hydride</a>.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Oxidizing_agent/1FQzB8pQ">Oxidizing agent</a></li> <li><a href="/facts/Reducing_agent/CtfSGVXC">Reducing agent</a></li> <li><a href="/facts/Transfer_hydrogenation/5IQkKatC">Transfer hydrogenation</a></li> <li><a href="/facts/Electrosynthesis/hzU3XYxC">Electrosynthesis</a></li></ul> <h3>Functional group oxidations</h3> <ul><li><a href="/facts/Alcohol_oxidation/FV12dlnW">Alcohol oxidation</a></li> <li><a href="/facts/Nitro_compound/pem2BhMY">Oxidation of oximes and primary amines to nitro compounds</a></li> <li><a href="/facts/Glycol_cleavage/fmQtKMzc">Glycol cleavage</a></li> <li><a href="/facts/Alpha_hydroxy_acid/c4wPcqHP">Oxidative cleavage of α-Hydroxy acids</a></li> <li><a href="/facts/Alkene/RtYcS6kU">Alkene oxidations</a></li> <li><a href="/facts/Nitrile/Gz7RCnC6">Oxidation of primary amines to nitriles</a></li> <li><a href="/facts/Thiol/VemKEDP9">Oxidation of thiols to sulfonic acids</a></li> <li><a href="/facts/Azo_compound/dnl1WKnK">Oxidation of hydrazines to azo compounds</a></li></ul> <h3>Functional group reductions</h3> <ul><li><a href="/facts/Carbonyl_reduction/yBplcaTD">Carbonyl reduction</a></li> <li><a href="/facts/Amide_reduction/kfPqxrFj">Amide reduction</a></li> <li><a href="/facts/Nitrile_reduction/jVTGcR1F">Nitrile reduction</a></li> <li><a href="/facts/Reduction_of_nitro_compounds/vkxlQ2RC">Reduction of nitro compounds</a></li> <li><a href="/facts/Hydrogenation_of_carbon%25E2%2580%2593nitrogen_double_bonds/SgvuDX5d">Reduction of imines and Schiff bases</a></li> <li><a href="/facts/Aromatic_hydrocarbon/3EXq8Tgf">Reduction of aromatic compounds to saturated rings</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>March Jerry; (1985). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc. ISBN 0-471-85472-7 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Organic Redox Systems: Synthesis, Properties, and Applications, Tohru Nishinaga 2016 <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>March Jerry; (1985). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc. ISBN 0-471-85472-7 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>http://www.electrosynthesis.com Link Archived 2008-05-15 at the Wayback Machine <a href="http://www.electrosynthesis.com" target="_blank">http://www.electrosynthesis.com</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Recupero, Francesco; Punta, Carlo (2007). "Free Radical Functionalization of Organic Compounds Catalyzed by N- Hydroxyphthalimide". Chemical Reviews. 107 (9): 3800–3842. doi:10.1021/cr040170k. PMID 17848093. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1 <a href="978-0-471-72091-1" target="_blank">978-0-471-72091-1</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> </ol>