11.5 Functional group interconversions
11 min read•august 21, 2024
Functional group interconversions are the backbone of organic synthesis, allowing chemists to transform molecules by changing their reactive centers. These reactions, including oxidations, reductions, and substitutions, enable the creation of complex compounds from simpler starting materials.
Understanding these transformations is crucial for predicting and controlling organic reactions. By mastering the principles of functional group interconversions, chemists can design efficient synthetic routes, optimize reaction conditions, and develop new methodologies for creating valuable organic compounds.
Types of functional groups
- Functional groups serve as reactive centers in organic molecules, determining their chemical behavior and properties
- Understanding functional groups is crucial for predicting and controlling organic reactions in synthesis and analysis
Common functional groups
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- Hydroxyl group (-OH) found in imparts polarity and hydrogen bonding capabilities
- Carbonyl group (C=O) present in and exhibits high reactivity towards nucleophiles
- Carboxyl group (-COOH) in carboxylic acids contributes to acidity and forms esters
- Amino group (-NH2) in amines acts as a base and nucleophile in various reactions
- Alkene (C=C) and alkyne (C≡C) groups undergo addition reactions due to their pi bonds
Functional group priorities
- Carboxylic acids take precedence over aldehydes and ketones in nomenclature
- Aldehydes have higher priority than ketones when both are present in a molecule
- Alcohols are prioritized over ethers in naming conventions
- Amines are given priority over alkyl groups in systematic naming
- Multiple functional groups are ranked based on their state and reactivity
Oxidation reactions
- Oxidation reactions involve the loss of electrons or increase in oxidation state of carbon atoms
- These transformations are fundamental in organic synthesis for introducing oxygen-containing functional groups
Alcohol oxidation
- oxidize to aldehydes using mild oxidants (PCC, Swern oxidation)
- Further oxidation of aldehydes yields carboxylic acids with strong oxidants (Jones reagent)
- form ketones upon oxidation with various reagents (, PCC)
- resist oxidation due to lack of α-hydrogen atoms
- Benzylic and allylic alcohols undergo oxidation more readily than aliphatic alcohols
Aldehyde oxidation
- Aldehydes oxidize to carboxylic acids using mild oxidants (Ag2O, Tollens' reagent)
- Fehling's solution and Benedict's reagent are used to detect reducing sugars through aldehyde oxidation
- Haloform reaction oxidizes methyl ketones to carboxylic acids with one less carbon
- Baeyer-Villiger oxidation converts aldehydes to formate esters using peroxy acids
Alkene oxidation
- Epoxidation of alkenes occurs with peroxyacids (m-CPBA) to form epoxides
- Dihydroxylation produces vicinal diols using OsO4 or cold, dilute KMnO4
- Ozonolysis cleaves carbon-carbon double bonds to form carbonyl compounds
- Allylic oxidation selectively oxidizes the carbon adjacent to a double bond (SeO2)
Reduction reactions
- reactions involve the gain of electrons or decrease in oxidation state of carbon atoms
- These processes are essential for converting higher oxidation state functional groups to lower ones
Carbonyl reduction
- Aldehydes and ketones reduce to primary and secondary alcohols using or
- Meerwein-Ponndorf-Verley reduction uses aluminum isopropoxide for chemoselective carbonyl reduction
- Wolff-Kishner reduction and Clemmensen reduction convert carbonyls to alkanes
- α,β-unsaturated carbonyls can undergo 1,2- or 1,4-reduction depending on conditions
Carboxylic acid reduction
- LiAlH4 reduces carboxylic acids to primary alcohols in two-electron steps
- Borane (BH3) selectively reduces carboxylic acids in the presence of esters
- Rosenmund reduction converts acyl chlorides to aldehydes using Pd/BaSO4 catalyst
- Thiol esters undergo selective reduction to aldehydes with Pd/C and H2
Nitro group reduction
- Catalytic hydrogenation (Pd/C, H2) reduces nitro groups to primary amines
- Tin and hydrochloric acid provide an alternative method for nitro reduction
- Zinc dust in acetic acid selectively reduces aromatic nitro compounds to anilines
- Partial reduction to hydroxylamines or nitroso compounds possible with controlled conditions
Nucleophilic substitution
- Nucleophilic reactions involve the replacement of one functional group by another
- These reactions are fundamental in organic synthesis for creating new carbon-heteroatom bonds
SN1 vs SN2 mechanisms
- SN2 reactions proceed via backside attack with inversion of stereochemistry
- SN1 reactions involve a carbocation intermediate leading to racemization or retention
- Primary substrates favor SN2, while tertiary substrates prefer SN1 mechanism
- Secondary substrates can undergo either SN1 or SN2 depending on conditions
- Solvent polarity and leaving group ability influence the preferred mechanism
Leaving group effects
- Good leaving groups (halides, tosylates) enhance the rate of nucleophilic substitution
- Hydroxyl groups become good leaving groups when protonated or converted to sulfonate esters
- Relative leaving group ability correlates with the stability of the conjugate base
- Fluoride is a poor leaving group due to its strong C-F bond
- Crown ethers can promote nucleophilic substitution by activating alkali metal cations
Elimination reactions
- result in the formation of multiple bonds by removing adjacent atoms
- These processes compete with substitution reactions and are crucial in alkene synthesis
E1 vs E2 mechanisms
- E2 reactions occur in one step with concerted base attack and leaving group departure
- E1 reactions proceed through a carbocation intermediate followed by proton loss
- Strong bases and primary substrates favor E2, while weak bases and tertiary substrates prefer E1
- E1 reactions can lead to rearrangement products due to carbocation intermediates
- and solvent polarity influence the competition between E1 and E2 pathways
Regioselectivity in eliminations
- Zaitsev's rule predicts formation of the more substituted alkene as the major product
- Hofmann elimination produces the less substituted alkene using bulky bases (t-BuOK)
- Anti-periplanar arrangement of leaving group and β-hydrogen favors elimination
- Neighboring group participation can direct regioselectivity in certain substrates
- Elimination-addition sequences allow for alkene isomerization and migration
Addition reactions
- Addition reactions involve the formation of new bonds across multiple bonds
- These transformations are key in functionalizing alkenes and alkynes
Electrophilic addition to alkenes
- Hydrohalogenation follows Markovnikov's rule with HX addition to alkenes
- Hydration of alkenes occurs via oxymercuration-demercuration or hydroboration-oxidation
- Halogenation produces vicinal dihalides through cyclic halonium ion intermediates
- Halohydrin formation results from alkene reaction with hypohalous acids (HOX)
- Epoxidation with peroxyacids creates three-membered cyclic ethers
Nucleophilic addition to carbonyls
- Grignard reagents add to aldehydes and ketones forming alcohols after workup
- Cyanohydrin formation occurs with HCN addition to carbonyls under basic conditions
- Imine and enamine formation result from primary and secondary amine addition respectively
- Wittig reaction converts carbonyls to alkenes using phosphonium ylides
- Aldol addition and condensation form β-hydroxy carbonyls and α,β-unsaturated carbonyls
Rearrangement reactions
- Rearrangement reactions involve the migration of atoms or groups within a molecule
- These processes can lead to unexpected products and are useful in synthesis
Carbocation rearrangements
- Wagner-Meerwein rearrangement involves 1,2-alkyl or 1,2-hydride shifts in carbocations
- Pinacol rearrangement converts vicinal diols to aldehydes or ketones under acidic conditions
- Beckmann rearrangement transforms oximes to amides with acid
- Curtius rearrangement converts acyl azides to isocyanates with loss of nitrogen
- Favorskii rearrangement of α-haloketones produces carboxylic acid derivatives
Sigmatropic rearrangements
- Cope rearrangement involves [3,3]-sigmatropic shift in 1,5-dienes
- Claisen rearrangement occurs in allyl vinyl ethers forming γ,δ-unsaturated carbonyl compounds
- Diels-Alder reaction can be followed by retro-Diels-Alder leading to rearranged products
- Oxy-Cope rearrangement proceeds through enolate intermediates with enhanced reaction rates
- Benzidine rearrangement converts hydrazobenzenes to benzidine derivatives
Protection and deprotection
- Protection strategies are crucial in multistep synthesis to prevent unwanted side reactions
- Deprotection conditions must be compatible with other functional groups present
Alcohol protection
- Silyl ethers (TBS, TBDPS) protect alcohols and are cleaved by fluoride ions
- Benzyl ethers offer robust protection and are removed by hydrogenolysis
- Acetals and ketals protect diols and are acid-labile
- MOM (methoxymethyl) ethers provide protection and are cleaved under acidic conditions
- Tetrahydropyranyl (THP) ethers are easily formed and removed under mild acidic conditions
Carbonyl protection
- Acetals and ketals protect aldehydes and ketones respectively using ethylene glycol
- 1,3-Dithianes protect carbonyls and allow for umpolung reactivity
- Enol ethers protect ketones and are hydrolyzed under acidic conditions
- Hydrazones and oximes serve as carbonyl protecting groups removable by mild hydrolysis
- Cyanohydrins protect aldehydes and regenerate carbonyls under basic conditions
Amine protection
- Carbamates (Boc, Cbz) protect amines and are cleaved under acidic or hydrogenolysis conditions
- Benzyl groups protect amines and are removed by catalytic hydrogenation
- Acetyl groups offer simple protection and are hydrolyzed under basic or acidic conditions
- Fmoc (9-fluorenylmethoxycarbonyl) groups are base-labile and used in peptide synthesis
- Phthalimides protect primary amines and are cleaved by hydrazine (Gabriel synthesis)
Functional group transformations
- Functional group transformations allow for the interconversion between different functional groups
- These reactions are essential for building complex molecules from simple precursors
Alcohol to alkyl halide
- Thionyl chloride (SOCl2) converts alcohols to alkyl chlorides with inversion of configuration
- PBr3 and PI3 transform alcohols to alkyl bromides and iodides respectively
- Appel reaction uses PPh3 and CCl4 to convert alcohols to alkyl chlorides
- Tosylation followed by SN2 with halide ion provides an alternative route
- Mitsunobu reaction inverts stereochemistry while replacing alcohol with various nucleophiles
Alkene to alcohol
- Hydroboration-oxidation yields anti-Markovnikov alcohol products
- Oxymercuration-demercuration gives Markovnikov alcohol addition products
- Epoxidation followed by hydrolysis produces vicinal diols
- Sharpless asymmetric dihydroxylation creates chiral vicinal diols
- Wacker oxidation converts terminal alkenes to methyl ketones
Ketone to alkene
- Wittig reaction uses phosphonium ylides to form alkenes from ketones
- Horner-Wadsworth-Emmons reaction employs phosphonate esters for E-selective alkene formation
- Peterson olefination utilizes α-silyl carbanions to generate alkenes
- McMurry coupling reductively couples two ketones to form alkenes
- Julia olefination involves the addition of sulfones to carbonyls followed by elimination
Synthesis strategies
- Synthesis strategies involve planning and executing multi-step transformations
- Efficient synthesis requires careful consideration of reaction sequences and conditions
Retrosynthetic analysis
- Disconnection approach breaks down complex targets into simpler precursors
- Functional group interconversions (FGIs) identify key intermediates in retrosynthesis
- Strategic bond disconnections focus on forming C-C bonds in the forward synthesis
- Symmetry considerations can simplify retrosynthetic analysis
- Convergent synthesis strategies often lead to more efficient synthetic routes
Forward synthesis planning
- Linear sequences build complexity through stepwise addition of functional groups
- Convergent approaches combine complex fragments in late-stage coupling reactions
- Protecting group strategies prevent unwanted side reactions in multistep syntheses
- One-pot reactions minimize isolation steps and increase overall efficiency
- Stereochemical control is crucial for synthesizing enantiomerically pure compounds
Reagents for interconversions
- Reagents play a crucial role in functional group interconversions
- Understanding reagent reactivity and selectivity is key to successful transformations
Oxidizing agents
- Chromium-based reagents (PCC, PDC) oxidize alcohols to aldehydes or ketones
- Permanganate (KMnO4) serves as a strong oxidant for alkenes and alcohols
- Peroxides (m-CPBA, H2O2) are used for epoxidation and Baeyer-Villiger oxidation
- Dess-Martin periodinane (DMP) provides mild oxidation of alcohols to carbonyls
- TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) catalyzes selective alcohol oxidations
Reducing agents
- Sodium borohydride (NaBH4) reduces aldehydes and ketones to alcohols
- Lithium aluminum hydride (LiAlH4) reduces esters and carboxylic acids to alcohols
- Catalytic hydrogenation (H2/Pd) reduces alkenes, alkynes, and various functional groups
- Dissolving metal reductions (Na/NH3) reduce alkynes to trans-alkenes
- DIBAL-H (diisobutylaluminum hydride) selectively reduces esters to aldehydes at low temperatures
Nucleophiles and electrophiles
- Grignard reagents serve as strong carbon nucleophiles in additions to carbonyls
- Lithium dialkylcuprates (organocuprates) act as soft nucleophiles in conjugate additions
- Hydride sources (NaBH4, LiAlH4) function as nucleophiles in carbonyl reductions
- Lewis acids (BF3, AlCl3) activate electrophiles in various reactions
- Halogenating agents (Br2, NBS) act as electrophiles in addition and substitution reactions
Reaction conditions
- Reaction conditions significantly influence the outcome of functional group interconversions
- Optimizing conditions is crucial for achieving desired selectivity and yield
Temperature effects
- Higher temperatures generally increase reaction rates but may decrease selectivity
- Low temperatures can enhance stereoselectivity in asymmetric reactions
- Thermodynamic vs kinetic control products often depend on reaction temperature
- Some reactions require specific temperature ranges to proceed efficiently
- Temperature ramps or gradients can be used to control reaction progress
Solvent effects
- Polar protic solvents (H2O, alcohols) can participate in hydrogen bonding
- Polar aprotic solvents (DMF, DMSO) dissolve a wide range of organic compounds
- Non-polar solvents (hexane, toluene) are used for water-sensitive reactions
- Coordinating solvents (THF, ether) can influence organometallic reagent reactivity
- Green solvents (water, supercritical CO2) are increasingly used for environmental reasons
Catalyst considerations
- Homogeneous catalysts (transition metal complexes) often provide high selectivity
- Heterogeneous catalysts (Pd/C, Raney Ni) are easily separated and often reusable
- Enzyme catalysts offer high stereoselectivity under mild conditions
- Phase-transfer catalysts facilitate reactions between immiscible reactants
- Photocatalysts enable unique transformations using visible light as an energy source
Stereochemistry in interconversions
- Stereochemical considerations are crucial in functional group interconversions
- Understanding and controlling stereochemistry is essential for synthesizing complex molecules
Retention vs inversion
- SN2 reactions proceed with inversion of configuration at the reaction center
- SN1 reactions can lead to racemization or retention depending on nucleophile approach
- Neighboring group participation can result in retention of configuration
- Mitsunobu reaction inverts stereochemistry in alcohol substitutions
- Double inversion sequences can be used to achieve overall retention
Racemization
- Racemization occurs when a chiral center loses its stereochemical integrity
- Base-catalyzed enolization of carbonyls can lead to racemization of α-stereocenters
- Carbocation intermediates often result in racemization due to planar geometry
- Some enzyme-catalyzed reactions can cause racemization under certain conditions
- Racemization can be useful in dynamic kinetic resolution processes
Multistep transformations
- Multistep transformations combine several reactions to achieve complex structural changes
- Efficient planning and execution of these sequences is key to successful synthesis
Sequential reactions
- Protecting group strategies allow for selective transformations in complex molecules
- Oxidation-reduction sequences can be used to invert stereochemistry at carbinol centers
- Functional group interconversions often involve multiple steps (alcohol to nitrile)
- Carbon-carbon bond forming reactions are often followed by functional group adjustments
- Stereochemical control may require multiple steps to achieve desired configuration
One-pot reactions
- Tandem reactions perform multiple transformations without isolating intermediates
- Domino reactions involve a sequence of intramolecular transformations
- In situ reagent generation can lead to more efficient one-pot processes
- Multicomponent reactions combine three or more reactants in a single operation
- One-pot sequences often improve overall yield by avoiding isolation losses
Industrial applications
- Functional group interconversions are widely used in industrial-scale synthesis
- Efficient and economical processes are crucial for commercial production
Pharmaceutical synthesis
- Chiral pool starting materials often undergo functional group modifications
- Protecting group strategies are employed in complex natural product syntheses
- Stereoselective reductions and oxidations are key steps in drug synthesis
- Cross-coupling reactions form carbon-carbon bonds in pharmaceutical intermediates
- Green chemistry principles guide the development of sustainable pharmaceutical processes
Polymer production
- Polymerization reactions often involve functional group transformations
- Functional group interconversions are used to modify polymer properties
- Cross-linking reactions alter physical properties of polymers
- Biodegradable polymers incorporate hydrolyzable functional groups
- Polymer end-group modifications tailor materials for specific applications
Key Terms to Review (23)
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.
Aldehydes: Aldehydes are organic compounds containing a carbonyl group (C=O) where the carbon is bonded to at least one hydrogen atom, making them distinct from ketones. This unique structure allows aldehydes to participate in various chemical reactions, particularly those involving nucleophiles, making them important intermediates in organic synthesis and a key feature in many biochemical processes.
Catalysts: Catalysts are substances that increase the rate of a chemical reaction without being consumed in the process. They work by lowering the activation energy required for the reaction to occur, allowing the reactants to convert to products more efficiently. This property makes them essential in many organic reactions, particularly those involving functional group interconversions, where they facilitate the transformation of one functional group into another with minimal energy input.
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.
Electrophilicity: Electrophilicity refers to the ability of a chemical species to act as an electrophile, meaning it is attracted to electrons and can accept an electron pair from a nucleophile during a chemical reaction. This characteristic is crucial in organic reactions, as electrophiles are often key players in mechanisms such as nucleophilic acyl substitution, functional group transformations, and organocopper reactions. Understanding electrophilicity helps in predicting reaction pathways and the reactivity of various organic compounds.
Elimination reactions: Elimination reactions are chemical processes where elements of a molecule are removed, resulting in the formation of a double or triple bond. This type of reaction is fundamental in organic chemistry, particularly in the synthesis of alkenes and alkynes, as it allows for the transformation of saturated compounds into unsaturated ones. They are closely linked to retrosynthetic analysis and functional group interconversions, as these reactions help strategize the breakdown and construction of complex molecules.
Geometric isomers: Geometric isomers are a type of stereoisomer that have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of groups around a double bond or a ring structure. This difference in arrangement can lead to varying physical and chemical properties, making the study of geometric isomers important in understanding reactivity and functional group interconversions.
Grignard reaction: The Grignard reaction is a powerful organic reaction that involves the formation of carbon-carbon bonds through the reaction of Grignard reagents with electrophiles. This reaction is crucial for synthesizing various organic compounds and allows for functional group interconversions, particularly involving aldehydes and ketones, by forming new carbon chains.
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.
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.
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.
Nucleophilicity: Nucleophilicity refers to the strength of a nucleophile, which is a species that donates an electron pair to form a chemical bond in a reaction. It indicates how readily a nucleophile can attack an electrophile and is influenced by factors like charge, electronegativity, and solvent effects. The concept plays a critical role in reactions involving heterocyclic aromatic compounds, the synthesis of amines, functional group interconversions, and the basicity and structure of amines.
Oxidation: Oxidation is a chemical process that involves the loss of electrons or an increase in oxidation state by a molecule, atom, or ion. This concept is fundamental in understanding various organic reactions, where the transformation of compounds often includes the introduction of oxygen or the removal of hydrogen. In many biological and chemical processes, oxidation plays a crucial role, such as in the metabolism of carbohydrates and the conversion of functional groups in organic molecules.
Primary Alcohols: Primary alcohols are a class of organic compounds that contain one hydroxyl group (-OH) attached to a carbon atom that is bonded to only one other carbon atom. This structure makes them distinct from secondary and tertiary alcohols, as the carbon bearing the hydroxyl group is at the end of the carbon chain, allowing for specific reactions and transformations in organic chemistry.
Reduction: Reduction is a chemical process that involves the gain of electrons or the decrease in oxidation state of a molecule, often resulting in the addition of hydrogen or the removal of oxygen. This transformation is essential for synthesizing various organic compounds, including amines, carbohydrates, and other functional groups, making it a cornerstone of organic chemistry reactions.
Secondary alcohols: Secondary alcohols are organic compounds characterized by a hydroxyl group (-OH) attached to a carbon atom that is connected to two other carbon atoms. This structure means they can be oxidized to form ketones, making them important in various functional group interconversions. The presence of the secondary carbon influences their reactivity, especially in reactions involving oxidation and reduction.
Solvent effects: Solvent effects refer to how the choice of solvent can influence the behavior and outcomes of chemical reactions, including reaction rates, equilibrium positions, and spectroscopic properties. The solvent can stabilize or destabilize certain intermediates or transition states, which in turn affects reactivity and selectivity in reactions, as well as the absorption characteristics observed in spectroscopy.
Structural Isomers: Structural isomers are compounds that have the same molecular formula but different arrangements of atoms, leading to distinct structures and properties. This variation can result from differences in the connectivity of atoms, where the same set of atoms is linked in various ways, influencing their chemical behavior and functional characteristics.
Substitution: Substitution is a fundamental reaction mechanism in organic chemistry where one functional group or atom in a molecule is replaced by another. This process is critical in modifying compounds to create desired products with different chemical properties, often facilitating further transformations in synthetic pathways. Understanding substitution reactions helps in grasping how various functional groups can be interconverted, which is vital in organic synthesis and the reactivity of diazonium compounds.
Temperature: Temperature is a measure of the average kinetic energy of the particles in a substance, reflecting how hot or cold that substance is. It plays a crucial role in determining the rates of chemical reactions, the stability of compounds, and the conditions under which various functional group interconversions and cross-coupling reactions occur. Changes in temperature can influence reaction pathways, product distributions, and overall reaction efficiency.
Tertiary alcohols: Tertiary alcohols are organic compounds characterized by the presence of a hydroxyl (-OH) group attached to a carbon atom that is connected to three other carbon atoms. This structure makes tertiary alcohols distinct in their reactivity and properties, particularly in functional group interconversions where they can be transformed into various other functional groups like alkyl halides or ketones through substitution or elimination reactions.
Wurtz Reaction: The Wurtz reaction is an organic reaction that involves the coupling of two alkyl halides in the presence of a sodium metal, resulting in the formation of a symmetrical alkane. This reaction is primarily used to synthesize larger alkanes from smaller alkyl halides and demonstrates the power of functional group interconversions, particularly how halogens can be replaced or utilized to create new carbon-carbon bonds.