Halogenation of alkanes
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halogenation reaction of alkanes by free radical mechanism free radical addition of halogen to the alkanes
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E1 reaction
The document discusses elimination reactions, specifically E1 and β-elimination reactions. It explains that E1 reactions proceed through a two-step unimolecular mechanism, with the first step being rate-determining. Factors that affect E1 reactions include the stability of the carbocation intermediate, steric effects, and the ability of the base to stabilize the carbocation. Rearrangements can also occur through carbocation migration to form more stable products.
E1 & E2 reaction tkkk.pptx
This document discusses elimination reactions, specifically the E1 and E2 mechanisms. The E2 reaction is a single step reaction where a base abstracts two substituents from a molecule to form an alkene. The E1 reaction is a two-step reaction where the leaving group departs first to form a carbocation, followed by deprotonation to form the alkene. Both reactions follow the Zaitsev rule, forming the more substituted alkene product. The Hoffman rule states that the major product comes from the β-carbon with the most hydrogens. Tertiary substrates undergo elimination most readily due to carbocation stability in the E1 and number of β-hydrogens in E2.
E1, E2 and SN1,SN2 Mechanisms.
The E1 reaction involves the slow loss of a leaving group to form a carbocation intermediate. This allows rearrangements to occur. A base is not required for the rate determining step. The E2 reaction is an elimination reaction that results in a product with one more degree of unsaturation. The SN1 reaction involves the formation of a carbocation intermediate through a unimolecular rate determining step. This can allow for nucleophilic attack from either side and possible racemization. The SN2 reaction involves synchronous breaking of one bond and formation of another in one step, leading to inversion of configuration.
Elimination reaction
- Elimination reactions occur by either an E1 or E2 mechanism. E1 is a one-step reaction involving a carbocation intermediate, while E2 is a concerted, single-step reaction.
- The E1 mechanism is favored by good leaving groups, stable carbocations, and weak bases. It is non-stereospecific and does not occur with primary alkyl halides. The E2 mechanism is favored by strong bases and polar aprotic solvents. It is stereospecific and proceeds through an anti-periplanar transition state.
- Key factors that determine the mechanism include the stability of carbocation intermediates, the strength of the leaving group and base, and steric
Introduction to Perkin reaction its mechanism and examples.pdf
The document summarizes the Perkin reaction, which was discovered in the 19th century by English chemist William Henry Perkin. The Perkin reaction involves the aldol condensation of an aromatic aldehyde and an acid anhydride catalyzed by the alkali salt of the acid. This reaction produces alpha, beta-unsaturated aromatic acids like cinnamic acid. The reaction proceeds through the abstraction of alpha hydrogen from the acid anhydride by the base, followed by the attack of the carbanion on the carbonyl carbon and an intramolecular acetyl shift to form the unsaturated product after loss of the acetate ion. The Perkin reaction is used commercially to produce various compounds.
Ozonolysis of alkenes
Ozonolysis is a reaction that cleaves carbon-carbon double bonds in alkenes using ozone, producing more oxidized carbonyl compounds such as aldehydes and ketones. The reaction occurs in several steps: ozone adds to the alkene to form an unstable molozonide intermediate which then rearranges to an ozonide. The ozonide is then treated with a reducing agent like zinc or dimethyl sulfide to yield carbonyl products, or an oxidizing agent like hydrogen peroxide to yield carboxylic acids.
Halogenation of alkanes
This document summarizes the halogenation of alkanes using free radical halogenation reactions with chlorine or bromine. The reaction involves three steps - initiation, propagation, and termination. In initiation, chlorine or bromine form free radicals. Propagation involves the addition of these free radicals to the alkane. Termination occurs when two radicals combine to form a non-radical product or molecule, ending the reaction. The stability of the radicals formed follows the order of tertiary > secondary > primary > methyl.
SN1 Reaction
SN1 reactions follow first-order kinetics. They proceed through a carbocation intermediate and can undergo carbocation rearrangement. The reaction is non-stereospecific, resulting in a racemic mixture of products with 50% inversion and 50% retention of configuration. Carbocation stability is influenced by inductive, hyperconjugation, and resonance effects. The reactivity of the substrate depends on the stability of the carbocation and follows the order of tertiary > secondary > primary > methyl substrates. The reaction requires a good leaving group and is favored in polar protic solvents.
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E1 reaction
The document discusses elimination reactions, specifically E1 and β-elimination reactions. It explains that E1 reactions proceed through a two-step unimolecular mechanism, with the first step being rate-determining. Factors that affect E1 reactions include the stability of the carbocation intermediate, steric effects, and the ability of the base to stabilize the carbocation. Rearrangements can also occur through carbocation migration to form more stable products.
E1 & E2 reaction tkkk.pptx
This document discusses elimination reactions, specifically the E1 and E2 mechanisms. The E2 reaction is a single step reaction where a base abstracts two substituents from a molecule to form an alkene. The E1 reaction is a two-step reaction where the leaving group departs first to form a carbocation, followed by deprotonation to form the alkene. Both reactions follow the Zaitsev rule, forming the more substituted alkene product. The Hoffman rule states that the major product comes from the β-carbon with the most hydrogens. Tertiary substrates undergo elimination most readily due to carbocation stability in the E1 and number of β-hydrogens in E2.
E1, E2 and SN1,SN2 Mechanisms.
The E1 reaction involves the slow loss of a leaving group to form a carbocation intermediate. This allows rearrangements to occur. A base is not required for the rate determining step. The E2 reaction is an elimination reaction that results in a product with one more degree of unsaturation. The SN1 reaction involves the formation of a carbocation intermediate through a unimolecular rate determining step. This can allow for nucleophilic attack from either side and possible racemization. The SN2 reaction involves synchronous breaking of one bond and formation of another in one step, leading to inversion of configuration.
Elimination reaction
- Elimination reactions occur by either an E1 or E2 mechanism. E1 is a one-step reaction involving a carbocation intermediate, while E2 is a concerted, single-step reaction.
- The E1 mechanism is favored by good leaving groups, stable carbocations, and weak bases. It is non-stereospecific and does not occur with primary alkyl halides. The E2 mechanism is favored by strong bases and polar aprotic solvents. It is stereospecific and proceeds through an anti-periplanar transition state.
- Key factors that determine the mechanism include the stability of carbocation intermediates, the strength of the leaving group and base, and steric
Introduction to Perkin reaction its mechanism and examples.pdf
The document summarizes the Perkin reaction, which was discovered in the 19th century by English chemist William Henry Perkin. The Perkin reaction involves the aldol condensation of an aromatic aldehyde and an acid anhydride catalyzed by the alkali salt of the acid. This reaction produces alpha, beta-unsaturated aromatic acids like cinnamic acid. The reaction proceeds through the abstraction of alpha hydrogen from the acid anhydride by the base, followed by the attack of the carbanion on the carbonyl carbon and an intramolecular acetyl shift to form the unsaturated product after loss of the acetate ion. The Perkin reaction is used commercially to produce various compounds.
Ozonolysis of alkenes
Ozonolysis is a reaction that cleaves carbon-carbon double bonds in alkenes using ozone, producing more oxidized carbonyl compounds such as aldehydes and ketones. The reaction occurs in several steps: ozone adds to the alkene to form an unstable molozonide intermediate which then rearranges to an ozonide. The ozonide is then treated with a reducing agent like zinc or dimethyl sulfide to yield carbonyl products, or an oxidizing agent like hydrogen peroxide to yield carboxylic acids.
Halogenation of alkanes
This document summarizes the halogenation of alkanes using free radical halogenation reactions with chlorine or bromine. The reaction involves three steps - initiation, propagation, and termination. In initiation, chlorine or bromine form free radicals. Propagation involves the addition of these free radicals to the alkane. Termination occurs when two radicals combine to form a non-radical product or molecule, ending the reaction. The stability of the radicals formed follows the order of tertiary > secondary > primary > methyl.
SN1 Reaction
SN1 reactions follow first-order kinetics. They proceed through a carbocation intermediate and can undergo carbocation rearrangement. The reaction is non-stereospecific, resulting in a racemic mixture of products with 50% inversion and 50% retention of configuration. Carbocation stability is influenced by inductive, hyperconjugation, and resonance effects. The reactivity of the substrate depends on the stability of the carbocation and follows the order of tertiary > secondary > primary > methyl substrates. The reaction requires a good leaving group and is favored in polar protic solvents.
Rearrangement of carbocation
The document discusses carbocations, which are carbon-containing molecules with a positive charge. It defines different types of carbocations based on the groups attached to the charged carbon atom, such as primary, secondary, tertiary, allylic, benzylic, vinyl, and phenyl carbocations. The document also discusses the structure, stability, and rearrangement of carbocations. Carbocations can rearrange into more stable configurations by shifting bonds to form secondary or tertiary carbocations. The stability of carbocations is affected by the number of carbon groups attached, neighboring electron-withdrawing groups, and hybridization of the charged carbon atom.
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favorskki rearrangement, Benzil benzilic acid rearrangement
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Crossed aldol condensation
The aldol condensation reaction involves the reaction of two carbonyl compounds in the presence of a strong base to form a β-hydroxyaldehyde or β-hydroxyketone. The reaction proceeds through the formation of an enolate ion intermediate that acts as a nucleophile, attacking the carbonyl carbon of the other molecule. This forms a carbon-carbon bond between the α-carbon of the donor molecule and the carbonyl carbon of the acceptor molecule. The aldol condensation reaction is useful for synthesizing larger molecules from simple starting materials and plays an important role in biochemical processes such as gluconeogenesis.
Nucleophilic Substitution reaction (SN1 reaction)
Attack of nucleophile at a saturated carbon atom bearing substituent, known as leaving group results in Substitution reaction.
The group that is displaced (leaving group) carries its bonding electrons.
The new bond is formed between nucleophile and the carbon using the electrons supplied by the nucleophilic agent.
The compound on which substitution takes place is called “substrate.”
The substrate consists of two parts, alkyl group and leaving group.
Favorskii Rearrangement reactions
Rearrangement reactions involve the migration of an atom or group within the same molecule. A 1,2-shift is a migration from one atom to an adjacent atom. The Favorskii rearrangement involves the rearrangement of cyclopropanones and α-halo ketones in the presence of a base, forming carboxylic acids or derivatives. For cyclic α-halo ketones, the Favorskii rearrangement causes a ring contraction from a 6-membered to a 5-membered ring.
Reaction of carbonyl compounds
THIS POWERPOINT CONTAIN REACTION OF CARBONYL COMPOUNDS WITH MACHANISM OF THE FOLLOWING
1. CONDENSATION
2. ALDOL CONDENSATION
3. CROSSED ALDOL CONDENSATION
4. CANNIZZARO REACTION
5. CROSSED CANNIZZARO REACTION
6. BENZOIN CONDENSATION
7. PERKIN CONDENSATION
Beckmann Rearrangement.pptx
The Beckmann rearrangement is a reaction that converts oximes to amides. Specifically, it is the acid-catalyzed transformation of a ketoxime to an N–substituted amide. This rearrangement occurs in the presence of strong acids like sulfuric acid or acid chlorides, and can be applied to oximes of both aryl and alkyl ketones as well as cyclic ketoximes. However, aldoximes typically undergo dehydration to form nitriles instead of amides under Beckmann rearrangement conditions.
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Cahn ingold-prelog projection formula
The Cahn–Ingold–Prelog (CIP) sequence rules, named for organic chemists Robert Sidney Cahn, Christopher Kelk Ingold, and Vladimir Prelog — alternatively termed the CIP priority rules, system, or conventions — are a standard process used in organic chemistry to completely and unequivocally name a stereoisomer of a molecule.
The purpose of the CIP system is to assign an R or S descriptor to each stereocenter and an E or Z descriptor to each double bond so that the configuration of the entire molecule can be specified uniquely by including the descriptors in its systematic name.
Substitution reactions
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Organic Intermediates
1) Heterolytic and homolytic bond fission can result in the formation of short-lived reaction intermediates called carbocations.
2) Carbocations are positively charged carbon ions that are electrophilic and undergo three reaction types: capture a nucleophile, lose a proton to form a pi bond, or rearrange.
3) Carbocation stability increases with increased substitution and the presence of electron donating groups, double bonds, or heteroatoms which delocalize the positive charge. Carbocations are key intermediates in SN1, E1, and rearrangement reactions.
Addition reactions on C-C double bond
1. The document discusses addition reactions of C-C multiple bonds, specifically alkenes and alkynes. It describes various reagents that add across the double or triple bonds, such as hydrogen halides, water, and halogens.
2. Markovnikov's rule is explained, stating that hydrogen adds to the carbon with more hydrogen substituents in alkene additions. Anti-Markovnikov additions are also possible using peroxides.
3. Methods to form alcohols from alkenes like acid-catalyzed hydration and oxymercuration-demercuration are described.
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1. The document discusses addition reactions of C-C multiple bonds, specifically alkenes and alkynes. It describes various reagents that add across the double or triple bonds, such as hydrogen halides, water, and halogens.
2. Markovnikov's rule is explained, stating that hydrogen adds to the carbon with more hydrogen substituents in alkene additions. Anti-Markovnikov additions are also possible using peroxides.
3. Methods to form alcohols from alkenes like acid-catalyzed hydration and oxymercuration-demercuration are described.
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You can watch this lecture video on youtube
https://youtu.be/bnQn7LunefE
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Follow at twitter:@LifeHobbies
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Crossed aldol condensation
The aldol condensation reaction involves the reaction of two carbonyl compounds in the presence of a strong base to form a β-hydroxyaldehyde or β-hydroxyketone. The reaction proceeds through the formation of an enolate ion intermediate that acts as a nucleophile, attacking the carbonyl carbon of the other molecule. This forms a carbon-carbon bond between the α-carbon of the donor molecule and the carbonyl carbon of the acceptor molecule. The aldol condensation reaction is useful for synthesizing larger molecules from simple starting materials and plays an important role in biochemical processes such as gluconeogenesis.
Nucleophilic Substitution reaction (SN1 reaction)
Attack of nucleophile at a saturated carbon atom bearing substituent, known as leaving group results in Substitution reaction.
The group that is displaced (leaving group) carries its bonding electrons.
The new bond is formed between nucleophile and the carbon using the electrons supplied by the nucleophilic agent.
The compound on which substitution takes place is called “substrate.”
The substrate consists of two parts, alkyl group and leaving group.
Favorskii Rearrangement reactions
Rearrangement reactions involve the migration of an atom or group within the same molecule. A 1,2-shift is a migration from one atom to an adjacent atom. The Favorskii rearrangement involves the rearrangement of cyclopropanones and α-halo ketones in the presence of a base, forming carboxylic acids or derivatives. For cyclic α-halo ketones, the Favorskii rearrangement causes a ring contraction from a 6-membered to a 5-membered ring.
Reaction of carbonyl compounds
THIS POWERPOINT CONTAIN REACTION OF CARBONYL COMPOUNDS WITH MACHANISM OF THE FOLLOWING
1. CONDENSATION
2. ALDOL CONDENSATION
3. CROSSED ALDOL CONDENSATION
4. CANNIZZARO REACTION
5. CROSSED CANNIZZARO REACTION
6. BENZOIN CONDENSATION
7. PERKIN CONDENSATION
Beckmann Rearrangement.pptx
The Beckmann rearrangement is a reaction that converts oximes to amides. Specifically, it is the acid-catalyzed transformation of a ketoxime to an N–substituted amide. This rearrangement occurs in the presence of strong acids like sulfuric acid or acid chlorides, and can be applied to oximes of both aryl and alkyl ketones as well as cyclic ketoximes. However, aldoximes typically undergo dehydration to form nitriles instead of amides under Beckmann rearrangement conditions.
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Alkenes can be prepared through various methods including reduction of alkynes, dehydrohalogenation of alkyl halides, dehydration of alcohols, and heating vicinal dihalogen derivatives with zinc dust. Addition reactions of alkenes follow Markovnikov's rule or anti-Markovnikov's rule in the presence of peroxides. Alkenes undergo addition reactions with halogens, hydrogen halides, water, sulfuric acid and undergo oxidation, ozonolysis, and polymerization.
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The purpose of the CIP system is to assign an R or S descriptor to each stereocenter and an E or Z descriptor to each double bond so that the configuration of the entire molecule can be specified uniquely by including the descriptors in its systematic name.
Substitution reactions
This document summarizes different types of substitution reactions in aliphatic and aromatic compounds. It describes three main types of substitution reactions: free radical substitution, electrophilic substitution, and nucleophilic substitution. Free radical substitution involves radicals and occurs in non-polar solvents. Electrophilic substitution can be aliphatic or aromatic and involves attack by an electrophile. Nucleophilic substitution involves displacement by a nucleophile and can proceed by SN1, SN2, or addition-elimination mechanisms. The document provides examples and details of the mechanisms and factors that influence each type of substitution reaction.
Organic Intermediates
1) Heterolytic and homolytic bond fission can result in the formation of short-lived reaction intermediates called carbocations.
2) Carbocations are positively charged carbon ions that are electrophilic and undergo three reaction types: capture a nucleophile, lose a proton to form a pi bond, or rearrange.
3) Carbocation stability increases with increased substitution and the presence of electron donating groups, double bonds, or heteroatoms which delocalize the positive charge. Carbocations are key intermediates in SN1, E1, and rearrangement reactions.
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3. The properties and reactions of haloalkanes and haloarenes are discussed. Important reactions include nucleophilic substitution and elimination reactions.
Haloalkanes and haloarenes.pptx
Haloalkanes are compounds containing one or more halogen atoms bonded to an alkyl group. They can be prepared through several methods including from alcohols using halogen acids, phosphorus halides, or thionyl chloride. Haloalkanes have higher boiling points and melting points than alkanes due to their polarity. They undergo nucleophilic substitution and elimination reactions. In SN1 reactions, a carbocation intermediate forms while SN2 reactions proceed through a transition state without separating charges. Tertiary haloalkanes undergo SN1 faster while primary haloalkanes undergo SN2 faster.
ch 9 haloalkanes and haloarenes ppt.ppt
Haloalkanes and haloarenes are organic compounds formed by replacing one or more hydrogen atoms in a hydrocarbon with halogen atoms. They are classified based on whether the halogen is attached to an aliphatic or aromatic group. Haloalkanes and haloarenes undergo nucleophilic substitution reactions with reagents such as hydroxide ion, cyanide ion, ammonia, and water. The rate of these substitution reactions depends on the strength of the carbon-halogen bond. In alcoholic solutions, haloalkanes react with hydroxide ion via an elimination mechanism to form alkenes. Haloalkanes are important intermediates in organic synthesis due to their reactivity and ease of preparation.
Haloalkanes.ppt
Haloalkanes and haloarenes are compounds formed by the replacement of hydrogen atoms in hydrocarbons by halogen atoms. This results in alkyl halides (haloalkanes) when the halogen is attached to an aliphatic skeleton, and aryl halides (haloarenes) when attached to an aromatic ring. They are important intermediates in organic synthesis due to their ease of preparation and high reactivity. Haloalkanes react through nucleophilic substitution, where the halogen is displaced by a nucleophile such as hydroxide, cyanide, ammonia or water. The rate depends on the strength of the carbon-halogen bond. In alcoholic solution, elimination occurs instead of substitution, producing
Chapter 3 Alkenes and Alkynes
This document provides an overview of alkenes and alkynes reactions. It discusses addition reactions of alkenes including hydrohalogenation, hydration, halogenation, hydrogenation, oxidation, and polymerization. It also covers conjugated dienes, the Diels-Alder reaction, and drawing resonance forms. For alkynes, the document discusses reduction, addition reactions, hydration, oxidative cleavage, acidity, and acetylide anion formation and reactions.
organic chemistry lecture module - Alkyl halides.pdf
This document provides an overview of alkyl halides for a medical biochemistry course. It defines alkyl halides as halogen-substituted alkanes and discusses their physical properties. Two common methods for preparing alkyl halides from alcohols are described: reaction with sulfur halides like thionyl chloride or phosphorus halides like phosphorus tribromide. The document also summarizes nucleophilic substitution reactions of alkyl halides and the SN1 and SN2 reaction mechanisms.
Alkanes
Introduction
Hybridization Of alkanes
Halogenations of Alkanes
Chlorination of Methane by Substitution
General Reaction of Alkanes
Org.chem_Lecture_5_Haloderivatives.pptx
Halohydrocarbons are derivatives of hydrocarbons where one or more hydrogen atoms are replaced by halogen atoms. There are several types including alkyl halides, aryl halides, vinyl halides, and benzyl halides. Halohydrocarbons can undergo nucleophilic substitution and elimination reactions. The reactivity depends on factors like the stability of carbocation intermediates, the nature of the leaving group, and solvent polarity. Vinyl and aryl halides are more resistant to substitution due to conjugation effects.
Alkanes
Alkanes are saturated hydrocarbons that contain only carbon and hydrogen. They have the general formula CnH2n+2 and contain single bonds between carbon atoms. Alkanes are highly stable due to weak polarization of carbon-hydrogen bonds. They undergo substitution reactions and reactions at high temperatures like halogenation and cracking. Alkanes can be synthesized by hydrogenation of alkenes/alkynes, reduction of alkyl halides, and Wurtz reaction.
Module-3_Lectures-2-5.pptx organic chemistry
The document describes various reactions of alkenes including hydration, hydroboration, epoxidation, and oxidation to 1,2-diols. It discusses the mechanisms and stereochemistry of acid-catalyzed hydration of alkenes, hydroboration-oxidation, and epoxidation using m-CPBA. It also covers the opening of epoxides to form anti- and syn-1,2-diols using acidic/basic conditions and the Prevost, Woodward, osmium tetroxide, and potassium permanganate oxidation methods.
Hydrogen - Chlorine Chain Reaction
Chain reactions involve reactive intermediates called chain carriers that propagate the reaction by producing more reactive intermediates. Chain reactions consist of initiation, propagation, and termination steps. The initiation step produces the first reactive intermediates. The propagation step produces more reactive intermediates from reaction of the previous intermediates. Termination stops the chain by deactivating the chain carriers. Chain reactions for forming HCl can occur thermally or photochemically. In the photochemical reaction, light initiates the production of chlorine atoms from Cl2, which then react with H2 through a series of propagation and termination steps to ultimately form HCl. The presence of oxygen complicates the reaction mechanism.
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Halogenation of alkanes
- 2. Halogenation Reaction A halogenation reaction is a chemical reaction between a substance and a halogen in which one or more halogen atoms are incorporated into molecules of the substance.
- 3. Halogenation of Alkanes Halogenation of an alkane produces a hydrocarbon derivative in which one or more halogen atoms have been substituted for hydrogen atoms. Alkanes are notoriously unreactive compounds because they are non-polar and lack functional groups at which reactions can take place. Free radical halogenation therefore provides a method by which alkanes can be functionalized.
- 4. A severe limitation of radical halogenation however is the number of similar C-H bonds that are present in all but the simplest alkanes, so selective reactions are difficult to achieve. General Reaction of Alkanes
- 5. Alkane halogenation is an example of a substitution reaction, a type of reaction that often occurs in organic chemistry. A substitution reaction is a chemical reaction in which part of a small reacting molecule replaces an atom or a group of atoms on a hydrocarbon or hydrocarbon derivative. A general equation for the substitution of a single halogen atom for one of the hydrogen atom of an alkane is
- 6. Chlorination of Methane by Substitution 1. In halogenation of an alkane, the alkane is said to undergo fluorination, chlorination, bromination or iodination depending on the identity of the halogen reactant. 2. Chlorination and bromination are the two widely used alkane halogenation reactions. 3. Fluorination reactions generally proceed too quickly to be useful and iodination reactions go too slowly.
- 7. 4. Halogenations usually result in the formation of a mixture of products rather than a single product. 5. More than one product results because more than one hydrogen atom on an alkane can be replaced with halogen atoms. 1. Initiation Step: The Cl-Cl bond of elemental chlorine undergoes hemolysis when irradiated with UV light, and this process yields two chlorine atoms, also called chlorine radicals.
- 8. 2. Propagation Step: A chlorine radical abstracts a hydrogen atom from methane to produce the methyl radical. The methyl radical in turn abstracts a chlorine atom from a chlorine molecule and chloromethane is formed. The second step of propagation also regenerates a chlorine atom. These steps repeat many times until termination occurs.
- 9. The reaction does not stop at this step, however because the chlorinated methane product can react with additional chlorine to produce polychlorinated products. By controlling the reaction conditions and the ratio of chlorine to methane. It is possible to favour formation of one or another of the possible chlorinated methane products.
- 10. 3. Termination Step: Termination takes place when a chlorine atom reacts with another chlorine atom to generate Cl2, or chlorine atom can react with a methyl radical to form chloromethane which constitutes a minor pathway by which the product is made. Two methyl radicals can also combine to produce ethane, a very minor by product of this reaction.