3.3 Oxidation and reduction of carbonyls
8 min read•august 21, 2024
Carbonyl oxidation and reduction reactions are essential tools in organic chemistry, allowing chemists to transform aldehydes and into higher or lower oxidation state compounds. These processes play a crucial role in organic synthesis, enabling the creation of complex molecules and functional group manipulations.
Understanding the mechanisms and reagents involved in carbonyl oxidation and reduction is key to predicting reaction outcomes and controlling stereochemistry. From mild oxidizing agents like to strong reducing agents like lithium aluminum hydride, chemists have a wide array of tools to achieve desired transformations.
Carbonyl oxidation reactions
- Carbonyl oxidation reactions transform aldehydes and ketones into higher oxidation state compounds
- These reactions play a crucial role in organic synthesis and metabolic processes
- Understanding carbonyl oxidation enables chemists to manipulate functional groups and create complex molecules
Oxidation of aldehydes
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- Aldehydes undergo oxidation to form
- Mild oxidizing agents (Tollens' reagent, ) used for aldehyde detection
- Strong oxidizing agents (, ) convert aldehydes to carboxylic acids
- Mechanism involves addition of water followed by hydride abstraction
Oxidation of primary alcohols
- Primary oxidize to aldehydes and then to carboxylic acids
- selectively oxidizes primary alcohols to aldehydes
- uses chromic acid to fully oxidize primary alcohols to carboxylic acids
- Controlled oxidation achieved through reaction conditions and reagent choice
Oxidation of secondary alcohols
- Secondary alcohols oxidize to ketones
- Oxidation stops at ketone stage due to lack of α-hydrogen
- Common oxidizing agents include PCC, Jones reagent, and
- Stereochemistry of alcohol affects reaction rate (equatorial alcohols oxidize faster)
Baeyer-Villiger oxidation
- Converts ketones to esters or cyclic ketones to lactones
- Involves insertion of oxygen atom between carbonyl carbon and adjacent carbon
- Peracids (m-CPBA) serve as oxidizing agents
- Migratory aptitude determines which group shifts (alkyl > aryl > H)
Carbonyl reduction reactions
- Carbonyl reduction reactions convert aldehydes and ketones to alcohols
- These transformations are fundamental in organic synthesis and pharmaceutical development
- Understanding reduction mechanisms aids in predicting stereochemical outcomes
Reduction of aldehydes
- Aldehydes reduce to primary alcohols
- () and lithium aluminum hydride () commonly used
- with H2 and metal catalysts (Pd/C) also effective
- Mechanism involves hydride addition followed by protonation
Reduction of ketones
- Ketones reduce to secondary alcohols
- Metal hydrides (NaBH4, LiAlH4) and catalytic hydrogenation employed
- Stereochemistry of product influenced by steric factors and reducing agent
- Chiral reducing agents enable enantioselective reductions
Reduction of esters
- Esters reduce to primary alcohols
- LiAlH4 reduces both C-O bonds, yielding two primary alcohols
- at low temperatures selectively reduces to aldehydes
- Mechanism involves tetrahedral intermediate formation and breakdown
Reduction of carboxylic acids
- Carboxylic acids reduce to primary alcohols
- LiAlH4 most commonly used due to its strong reducing power
- Borane (BH3) also effective for carboxylic acid reduction
- Two-step process involves formation of acyl hydride intermediate
Oxidizing agents
- Oxidizing agents facilitate the removal of electrons or hydrogen atoms from substrates
- Selection of appropriate oxidizing agent crucial for achieving desired selectivity and yield
- Understanding oxidizing agent reactivity helps in designing efficient synthetic routes
Chromium-based oxidants
- Chromium(VI) compounds widely used in organic oxidations
- Jones reagent (H2CrO4) oxidizes alcohols to carbonyl compounds
- Pyridinium chlorochromate (PCC) provides milder, more selective oxidation
- Collins reagent (·2Py) useful for oxidizing allylic and benzylic alcohols
Permanganate oxidation
- Potassium permanganate () serves as a strong oxidizing agent
- lead to complete oxidation of alkenes to carboxylic acids
- Basic conditions result in dihydroxylation of alkenes
- Permanganate cleaves glycols to form carbonyl compounds
Periodinane compounds
- Dess-Martin periodinane (DMP) provides mild, selective oxidation of alcohols
- IBX (2-iodoxybenzoic acid) oxidizes primary and secondary alcohols
- Periodinanes tolerate sensitive functional groups
- Mechanism involves ligand exchange and hypervalent iodine intermediates
Swern oxidation
- Converts primary and secondary alcohols to aldehydes and ketones
- Uses DMSO activated by oxalyl chloride or trifluoroacetic anhydride
- Proceeds under mild conditions at low temperatures
- Mechanism involves formation of sulfonium intermediate
Reducing agents
- Reducing agents provide electrons or hydrogen atoms to substrates
- Choice of reducing agent impacts reaction selectivity and product stereochemistry
- Understanding reducing agent properties enables precise control of reduction reactions
Metal hydrides
- Sodium borohydride (NaBH4) reduces aldehydes and ketones to alcohols
- Lithium aluminum hydride (LiAlH4) reduces esters, carboxylic acids, and nitriles
- DIBAL-H (diisobutylaluminum hydride) allows selective reduction of esters to aldehydes
- L-Selectride provides stereoselective reductions of ketones
Catalytic hydrogenation
- Uses hydrogen gas (H2) with metal catalysts (Pd, Pt, Ni)
- Reduces alkenes, alkynes, carbonyls, and aromatic compounds
- Catalyst choice affects selectivity and reaction conditions
- Mechanism involves adsorption of substrate and H2 on catalyst surface
Wolff-Kishner reduction
- Converts aldehydes and ketones to alkanes
- Uses hydrazine and strong base (KOH) under heating
- Proceeds through hydrazone intermediate
- Tolerates base-sensitive functional groups
Clemmensen reduction
- Reduces aldehydes and ketones to alkanes using zinc amalgam and HCl
- Effective for aromatic ketones and aldehydes
- Mechanism involves organozinc intermediates
- Works well in acidic conditions, complementing
Reaction mechanisms
- Understanding reaction mechanisms crucial for predicting outcomes and designing syntheses
- Mechanisms explain observed selectivity and guide optimization of reaction conditions
- Knowledge of mechanisms aids in troubleshooting and improving synthetic procedures
Oxidation mechanism
- Oxidation often proceeds through hydride abstraction
- Chromium-based oxidations involve chromate ester intermediates
- Permanganate oxidations form cyclic manganate esters
- Periodinane oxidations utilize hypervalent iodine species
Reduction mechanism
- Reductions typically involve hydride addition to electrophilic carbons
- Metal hydride reductions proceed through tetrahedral intermediates
- Catalytic hydrogenations involve surface-adsorbed species
- Wolff-Kishner reduction forms carbanionic intermediates
Hydride transfer
- Hydride ion (H-) transfers from reducing agent to substrate
- Stereochemistry of hydride addition affects product configuration
- Intramolecular hydride transfers occur in certain rearrangements (Meerwein-Ponndorf-Verley reduction)
- Biological hydride transfers often use NADH as cofactor
Electron transfer
- Single electron transfer (SET) mechanisms common in certain reductions
- Birch reduction of aromatic compounds proceeds via radical anion intermediates
- Electron transfer can lead to radical coupling or disproportionation
- Understanding SET processes important in electrochemical reactions
Stereochemistry in reductions
- Stereochemical control in reductions crucial for synthesizing specific isomers
- Substrate structure and reducing agent properties influence stereochemical outcome
- Predictive models guide selection of conditions for desired stereochemistry
Cram's rule
- Predicts stereochemistry of to carbonyls with adjacent
- Large group on chiral center orients away from incoming nucleophile
- Applies to reduction of α-chiral aldehydes and ketones
- Steric interactions between substrate and reducing agent drive selectivity
Felkin-Anh model
- Refined model for predicting stereochemistry in carbonyl reductions
- Considers electronic effects in addition to steric factors
- Largest group aligns perpendicular to carbonyl plane
- Nucleophile approaches from least hindered side, opposite to large group
Prelog's rule
- Predicts stereochemistry in reduction of cyclic ketones
- Hydride attack occurs from less hindered face of molecule
- Considers ring size and substituent orientation
- Useful for predicting major products in steroid and terpene reductions
Selective oxidation and reduction
- Selective transformations allow precise manipulation of complex molecules
- Understanding factors affecting selectivity enables efficient synthetic strategies
- Selective reactions minimize need for protecting groups and improve overall yield
Chemoselectivity
- Ability to react with one functional group in presence of others
- Sodium borohydride reduces aldehydes and ketones but not esters
- Wacker oxidation selectively oxidizes terminal alkenes to methyl ketones
- Reagent choice and reaction conditions crucial for achieving chemoselectivity
Regioselectivity
- Preferential reaction at one site over others in molecule
- Epoxidation of allylic alcohols occurs on more substituted alkene face
- Hydroboration-oxidation of alkenes favors anti-Markovnikov product
- Substrate structure and reagent properties influence regioselectivity
Stereoselectivity
- Control over formation of specific stereoisomers
- Asymmetric reductions using chiral catalysts or reagents
- Noyori hydrogenation achieves high enantioselectivity in ketone reduction
- Sharpless epoxidation provides enantioselective epoxidation of allylic alcohols
Applications in synthesis
- Oxidation and reduction reactions form backbone of many synthetic strategies
- These transformations enable construction of complex natural products and pharmaceuticals
- Skilled application of redox chemistry essential for efficient total synthesis
Functional group interconversions
- Oxidation and reduction allow conversion between related functional groups
- Alcohols oxidize to aldehydes, ketones, or carboxylic acids
- Nitriles reduce to primary amines via aldehydes
- Esters reduce to alcohols or aldehydes depending on conditions
Oxidation state manipulation
- Strategic oxidation or reduction alters molecular oxidation state
- Oxidative cleavage of alkenes produces carbonyl compounds
- Reductive amination converts carbonyls to amines
- Controlled oxidation state changes key to multi-step syntheses
Synthetic strategies
- Redox reactions often serve as key steps in retrosynthetic analysis
- Oxidative cyclizations form complex ring systems
- Reductive couplings join molecular fragments
- Strategic redox manipulations can simplify synthetic routes
Biological oxidation and reduction
- Biological redox reactions drive cellular metabolism and energy production
- Understanding biochemical redox processes aids drug design and biotechnology
- Many organic redox principles apply to enzymatic systems
Enzyme-catalyzed reactions
- Oxidoreductase enzymes catalyze biological redox reactions
- Alcohol dehydrogenase oxidizes alcohols to aldehydes or ketones
- Cytochrome P450 enzymes perform diverse oxidations in metabolism
- Ketoreductases enable enantioselective carbonyl reductions
Cofactors in redox reactions
- Nicotinamide adenine dinucleotide (NAD+/NADH) serves as biological hydride carrier
- Flavin adenine dinucleotide (FAD/FADH2) involved in two-electron transfers
- Coenzyme Q (ubiquinone) functions in electron transport chain
- Understanding cofactor chemistry crucial for studying metabolic pathways
Metabolic pathways
- Glycolysis oxidizes glucose to pyruvate, generating NADH
- Citric acid cycle involves series of oxidation and decarboxylation steps
- Fatty acid β-oxidation degrades lipids through repeated oxidation cycles
- Electron transport chain couples redox reactions to ATP synthesis
Analytical techniques
- Analytical methods essential for characterizing carbonyl compounds and their reactions
- Combination of techniques provides comprehensive structural and purity information
- Understanding analytical principles aids in reaction monitoring and product identification
Spectroscopic analysis
- Infrared (IR) spectroscopy detects characteristic carbonyl stretching frequencies
- Nuclear Magnetic Resonance () reveals chemical environment of carbons and hydrogens
- Mass spectrometry provides molecular weight and fragmentation patterns
- UV-Vis spectroscopy useful for conjugated carbonyl systems
Chromatographic methods
- Thin-layer chromatography (TLC) monitors reaction progress
- Gas chromatography (GC) separates volatile carbonyl compounds
- High-performance liquid chromatography (HPLC) analyzes non-volatile carbonyls
- Chiral chromatography separates enantiomers in stereoselective reactions
Chemical tests for carbonyls
- 2,4-Dinitrophenylhydrazine (Brady's reagent) forms colored precipitates with carbonyls
- Tollens' test (silver mirror) distinguishes aldehydes from ketones
- Iodoform test detects methyl ketones
- Fehling's and Benedict's solutions identify reducing sugars
Key Terms to Review (33)
Acidic Conditions: Acidic conditions refer to an environment where the pH is lower than 7, indicating the presence of excess hydrogen ions (H+). In organic chemistry, these conditions can greatly influence reaction mechanisms, stability of intermediates, and the outcomes of various transformations involving functional groups. Understanding how acidic conditions affect reactions involving carbonyl compounds and their derivatives is crucial for predicting product formation and reaction pathways.
Alcohols: Alcohols are organic compounds characterized by the presence of one or more hydroxyl (-OH) functional groups attached to a carbon atom. They play crucial roles in organic reactions, particularly in oxidation and reduction processes, and are involved in the synthesis of various natural products and complex molecules.
Aqueous workup: Aqueous workup is a process used in organic chemistry to purify reaction mixtures by removing unwanted water-soluble substances after a reaction, often following an organic synthesis. This technique typically involves the addition of water to the organic layer, allowing for the separation of products and impurities based on their solubility in different phases. It plays a vital role in the context of oxidation and reduction reactions involving carbonyl compounds, as it helps isolate desired products from byproducts and solvents.
Baeyer-Villiger Oxidation: Baeyer-Villiger oxidation is a chemical reaction that involves the conversion of ketones to esters through the action of peracids. This transformation is significant as it showcases a specific method for oxidizing carbonyl compounds while simultaneously introducing new functional groups. It demonstrates the importance of oxidizing agents in organic synthesis and how they can alter molecular structures while maintaining certain elements of the original compound.
Carboxylic Acids: Carboxylic acids are organic compounds characterized by the presence of one or more carboxyl groups ($$-COOH$$). They are known for their acidic properties due to the ability of the carboxyl group to donate a proton. These compounds are vital in various chemical reactions and play significant roles in biological processes, making them important in multiple areas, including oxidation and reduction reactions, amine synthesis, natural product chemistry, and retrosynthetic analysis.
Catalytic hydrogenation: Catalytic hydrogenation is a chemical reaction that involves the addition of hydrogen to unsaturated organic compounds, typically alkenes and alkynes, in the presence of a catalyst. This process converts these unsaturated compounds into saturated ones, effectively reducing the number of double or triple bonds present. It plays a significant role in the reduction of carbonyl compounds, where carbonyl groups are transformed into alcohols, demonstrating its importance in organic synthesis.
Chiral Centers: Chiral centers, also known as stereogenic centers, are atoms in a molecule that have four different substituents attached to them, leading to non-superimposable mirror images or enantiomers. This property is crucial in organic chemistry because the different spatial arrangements can result in vastly different chemical behaviors and biological activities, especially when dealing with molecules like carbonyls that can undergo oxidation and reduction reactions.
Chromic Acid: Chromic acid is a powerful oxidizing agent commonly used in organic chemistry for the oxidation of alcohols and aldehydes to their corresponding carbonyl compounds. It is often represented by the chemical formula H2CrO4, and its strong oxidative properties make it essential in transforming primary and secondary alcohols into aldehydes and ketones respectively.
Clemmensen Reduction: Clemmensen reduction is a chemical reaction used to convert carbonyl compounds, such as aldehydes and ketones, into alkanes through the use of zinc amalgam and hydrochloric acid. This process is particularly effective for reducing compounds that are sensitive to strong basic or acidic conditions, making it a valuable method in organic synthesis for removing functional groups while preserving the overall structure of the molecule.
Cram's Rule: Cram's Rule is a guideline in organic chemistry that helps predict the stereochemistry of certain reaction products, particularly in reactions involving carbonyl compounds and their derivatives. It specifically focuses on the orientation of substituents in the formation of products from nucleophilic addition to carbonyls, emphasizing how steric factors influence which side of the carbonyl the nucleophile will approach.
CrO3: CrO3, or chromium trioxide, is a powerful oxidizing agent commonly used in organic chemistry for the oxidation of alcohols and aldehydes to their corresponding carbonyl compounds. It plays a crucial role in various oxidation reactions, particularly in the conversion of primary and secondary alcohols to aldehydes and ketones, as well as in the oxidative cleavage of certain carbon-carbon double bonds.
Dess-Martin Periodinane: Dess-Martin Periodinane is a mild and efficient oxidizing agent used primarily for the conversion of alcohols to carbonyl compounds such as aldehydes and ketones. This reagent is particularly favored in organic synthesis due to its selectivity, minimal side reactions, and the ability to operate under mild conditions, which preserves sensitive functional groups during oxidation processes.
DIBAL-H: DIBAL-H, or diisobutylaluminum hydride, is a powerful reducing agent commonly used in organic chemistry, especially for the selective reduction of carbonyl compounds to their corresponding alcohols. It is particularly effective in reducing esters and aldehydes while leaving ketones largely unaffected. Its unique reactivity makes it a valuable tool in transforming carboxylic acids into alcohols without affecting other functional groups.
Fehling's Solution: Fehling's Solution is a chemical reagent used to test for the presence of reducing sugars, specifically aldehydes. It is composed of two separate solutions: Fehling's A, which contains copper(II) sulfate, and Fehling's B, which contains a mixture of sodium potassium tartrate and sodium hydroxide. When mixed and heated with a reducing sugar, the copper(II) ions in Fehling's Solution are reduced to copper(I) oxide, forming a characteristic red precipitate, indicating oxidation of the sugar.
Felkin-Anh Model: The Felkin-Anh model is a theoretical framework used to predict the stereochemical outcomes of nucleophilic additions to carbonyl compounds. It emphasizes the role of sterics and electronic effects in determining which face of the carbonyl is attacked by the nucleophile, influencing the configuration of the resulting product. This model is particularly important in understanding how various substituents on the carbonyl compound can steer the approach of nucleophiles during reactions.
Hydride Transfer: Hydride transfer is a chemical reaction where a hydride ion (H\text{-}) is transferred from one molecule to another, often resulting in the reduction of a carbonyl compound. This process plays a critical role in organic chemistry, particularly in the reduction of aldehydes and ketones to their corresponding alcohols. Hydride transfer is commonly facilitated by reducing agents, which donate the hydride ion, making it an essential mechanism in the context of carbonyl chemistry.
IR Spectroscopy: IR spectroscopy, or infrared spectroscopy, is an analytical technique used to identify and study the molecular composition of a substance by measuring how it interacts with infrared radiation. This method is particularly useful for analyzing functional groups in organic compounds, as different bonds absorb infrared light at specific wavelengths, resulting in a spectrum that can reveal the presence of various chemical structures.
Jones Oxidation: Jones oxidation is a chemical reaction used to oxidize primary and secondary alcohols to their corresponding carbonyl compounds, typically aldehydes and ketones, respectively. This transformation is facilitated by the use of chromium trioxide (CrO3) in an acidic medium, which acts as a strong oxidizing agent, effectively converting the alcohol functional group into a carbonyl group while producing chromium(III) species as a byproduct.
Ketones: Ketones are organic compounds characterized by a carbonyl group (C=O) bonded to two carbon atoms. They play a crucial role in various chemical reactions and processes, often serving as key intermediates in synthesis and transformations involving carbonyl compounds.
KMnO4: KMnO4, or potassium permanganate, is a strong oxidizing agent commonly used in organic chemistry for oxidation reactions. It has a deep purple color and can oxidize a wide range of organic compounds, particularly carbonyl compounds, to yield various products depending on the conditions of the reaction. Its versatility makes it a valuable reagent for both laboratory synthesis and analytical purposes.
LiAlH4: Lithium aluminum hydride (LiAlH4) is a powerful reducing agent commonly used in organic chemistry to reduce various functional groups, particularly carbonyls and esters. Its ability to donate hydride ions makes it invaluable in the transformation of carbonyl compounds into alcohols, and it also plays a crucial role in the interconversion of functional groups within organic synthesis.
NaBH4: Sodium borohydride (NaBH4) is a powerful reducing agent commonly used in organic chemistry to convert carbonyl compounds, such as aldehydes and ketones, into their corresponding alcohols. This versatile reagent plays a crucial role in various chemical transformations, impacting the reactivity and functional group interconversion of organic molecules, including esters and carbohydrates.
NMR: Nuclear Magnetic Resonance (NMR) is a powerful analytical technique used to determine the structure of organic compounds by observing the magnetic properties of atomic nuclei. This method provides detailed information about the number of hydrogen atoms in different environments, connectivity between atoms, and can also be applied to study carbon atoms. The resonance of nuclei in a magnetic field allows chemists to gather insights about molecular structure, which is particularly useful in analyzing carbonyl compounds during their oxidation and reduction processes.
Nucleophilic Addition: Nucleophilic addition is a chemical reaction where a nucleophile forms a bond with an electrophilic center, typically in carbonyl compounds like aldehydes and ketones. This process is central to many organic reactions, leading to the formation of alcohols and larger molecules through the addition of various nucleophiles to carbonyl carbons.
Oxidation of Aldehydes: The oxidation of aldehydes refers to the chemical process in which an aldehyde compound loses electrons or gains oxygen, leading to the formation of a carboxylic acid. This reaction highlights the reactivity of aldehydes due to their terminal carbonyl group, making them more susceptible to oxidation compared to ketones. Understanding this process is essential as it connects to broader concepts like redox reactions and the behavior of carbonyl compounds in organic chemistry.
Potassium permanganate: Potassium permanganate is a strong oxidizing agent with the chemical formula KMnO₄. It is commonly used in organic chemistry for the oxidation of various functional groups, particularly carbonyl compounds, facilitating transformations that can convert alcohols to ketones or aldehydes to carboxylic acids.
Prelog's Rule: Prelog's Rule is a principle used in organic chemistry to determine the stereochemistry of certain carbonyl compounds during oxidation and reduction reactions. This rule helps predict the favored pathways and products of these reactions based on the steric and electronic environment around the carbonyl carbon, guiding chemists in understanding how specific substituents influence reactivity.
Pyridinium chlorochromate (PCC): Pyridinium chlorochromate (PCC) is a chemical reagent commonly used in organic chemistry for the selective oxidation of alcohols to aldehydes and ketones. It stands out as a valuable tool for chemists due to its ability to oxidize primary and secondary alcohols without further oxidizing aldehydes into carboxylic acids, making it a go-to choice in various synthetic pathways.
Reduction of Ketones: The reduction of ketones is a chemical process in which a ketone, characterized by a carbonyl group ($$C=O$$) bonded to two other carbon atoms, is converted into a corresponding alcohol through the gain of electrons or hydrogen. This transformation typically involves the addition of a reducing agent, such as lithium aluminum hydride or sodium borohydride, which donates hydride ions ($$H^-$$) to the carbonyl carbon. Understanding this process is crucial as it illustrates the fundamental principles of redox chemistry and the reactivity of carbonyl compounds.
Sodium Borohydride: Sodium borohydride is a chemical compound with the formula NaBH4, widely recognized as a powerful reducing agent. It is commonly used in organic synthesis to reduce carbonyl compounds such as aldehydes and ketones into their corresponding alcohols, highlighting its importance in nucleophilic addition reactions. The ability of sodium borohydride to selectively reduce carbonyl groups while leaving other functional groups intact makes it a valuable tool in organic chemistry.
Stereoselectivity: Stereoselectivity is the preference of a chemical reaction to produce one stereoisomer over another when multiple stereoisomers are possible. This property is crucial in organic chemistry as it directly influences the biological activity and properties of the compounds formed, making it vital for the development of pharmaceuticals and other chemical products.
Tollens' Reagent: Tollens' reagent is a chemical solution used to detect the presence of aldehydes, consisting primarily of silver nitrate dissolved in ammonia. It acts as an oxidizing agent, specifically oxidizing aldehydes to their corresponding carboxylic acids while simultaneously reducing silver ions to metallic silver. This unique reaction is vital for distinguishing aldehydes from ketones in organic compounds.
Wolff-Kishner Reduction: The Wolff-Kishner reduction is a chemical reaction used to convert carbonyl compounds, such as ketones or aldehydes, into alkanes through the use of hydrazine and a strong base, typically potassium hydroxide, under heating. This reduction process effectively removes the oxygen atom of the carbonyl group, replacing it with hydrogen atoms, thus yielding a saturated hydrocarbon. It is particularly useful in organic synthesis when one wants to avoid the use of metal reagents that may be involved in other reduction methods.