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If a molecule has several potential reactive sites, the reaction will occur in the most reactive one. When comparing carbon-halogen bonds, lighter halogens such as fluorine and chlorine have a better orbital overlap with carbon, which makes the bond stronger. Bromine and iodine, on the other hand,
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Most chemical reactions bring together atoms that have negative charge character and atoms that have positive charge character. When evaluating possible reaction outcomes, several factors should be considered. The most important being identifying where in the molecule has the most
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are the most reactive because the hydrogen next to the carbon is small and only has one electron, and therefore does not provide steric or electronic shielding. By switching the hydrogen for a carbon group, making a
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would mostly target the aldehyde, even if it has the option to react with the ester. Chemoselectivity is an area of interest in chemistry because scientists want to recreate complex biological compounds, such as
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Different hydride reagents have different reactivity towards functional groups so they can be selected according to the desired outcome. Examples include the greater relative chemoselectivity of
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121:, the carbonyl becomes less reactive since the carbon is bigger and has more electrons. The most stable carbonyls are the ones with atoms with lone pairs next to them, such as
421:"Lanthanoids in organic synthesis. 6. Reduction of .alpha.-enones by sodium borohydride in the presence of lanthanoid chlorides: synthetic and mechanistic aspects"
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than nitrogen and therefore it concentrates more of the electron density on itself. Chemists take advantage of the stability of amides by using them as
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Some reagents have higher affinity with specific functional groups, which can be used to direct reactivity. A famous example is the
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of 4-nitro-2-chlorobenzonitrile to the corresponding aniline, 4-amino-2-chlorobenzonitrile. In another example, the compound
546:"pH-Controlled Oxidation of an Aromatic Ketone: Structural Elucidation of the Products of Two Green Chemical Reactions"
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and where has the least. This analysis gives a good prediction of reactivity, but more factors such as connectivity,
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can be ranked by evaluating how much electron density the neighbouring atoms donate to the carbonyl carbon.
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is the preferential reaction of a chemical reagent with one of two or more different functional groups.
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Alexakis, A.; Bäckvall, J. E.; Krause, N.; Pàmies, O.; Diéguez, M. (2008-08-01).
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metal makes the carbonyl of a conjugated ketone more reactive and directs the
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398:. A Wiley-Interscience publication (3. ed.). New York Weinheim: Wiley.
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258:(3rd ed.). International Union of Pure and Applied Chemistry. 2006.
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are bigger and therefore can undergo chemical reactions more easily.
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The carbon-bromine bond is more reactive than the carbon-fluorine bond
507:"The functional group selectivity of complex hydride reducing agents"
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Shenvi, Ryan A.; O’Malley, Daniel P.; Baran, Phil S. (2009-04-21).
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279:"Chemoselectivity: The Mother of Invention in Total Synthesis"
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Selective and unselective reduction of a conjugated ketone
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Reactivity ranking of common carbonyl functional groups
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Gemal, Andre L.; Luche, Jean Louis (September 1981).
394:Greene, Theodora W.; Wuts, Peter G. M. (1999).
137:to shield sites that they don't want to react.
369:Ouellette, Robert J.; Rawn, J. David (1996).
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50:, and make specific modifications to them.
373:. Upper Saddle River, N.J: Prentice Hall.
345:(2nd ed.). Lexinton, MA, USA: HEATH.
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425:Journal of the American Chemical Society
256:IUPAC Compendium of Chemical Terminology
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266:– via Online version 3.0.1, 2019.
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396:Protective groups in organic synthesis
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252:"Chemoselectivity (chemoselective)"
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544:Ballard, C. Eric (2010-01-12).
177:Reducing and oxidizing reagents
33:In a chemoselective system, a
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550:Journal of Chemical Education
283:Accounts of Chemical Research
341:Zumdahl, Steven S. (1995).
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173:into a conjugated ketone.
141:Metal-assisted selectivity
96:Carbonyl functional groups
505:Walker, E. R. H. (1976).
187:lithium aluminium hydride
511:Chemical Society Reviews
205:at high pH (forming the
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37:in the presence of an
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523:10.1039/cs9760500023
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437:10.1021/ja00408a029
343:Chemical Principles
598:Chemical reactions
209:) and oxidized by
183:sodium borohydride
167:conjugate addition
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108:The reactivity of
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570:10.1021/ed800054s
476:10.1021/cr0683515
431:(18): 5454–5459.
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380:978-0-02-390171-3
371:Organic chemistry
295:10.1021/ar800182r
232:Stereoselectivity
135:protecting groups
16:(Redirected from
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445:0002-7863
303:0001-4842
191:reduction
159:oxophilic
114:Aldehydes
110:carbonyls
75:Main page
62:overlap,
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221:See also
213:(to the
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