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Of alkyl halides

N,N,N, N -tetramethyl-l,8,-naph-thalenediamiDe M.P. 51 C. A remarkably strong mono-acidic base (pKg 12-3) which is almost completely non-nucleophilic and valuable for promoting organic elimination reactions (e.g. of alkyl halides to alkenes) without substitution. [Pg.60]

Sheppard N and De La Cruz C 1998 Vibrational spectra of hydrocarbons adsorbed on metals. Part II. Adsorbed acyclic alkynes and alkanes, cyclic hydrocarbons including aromatics and surface hydrocarbon groups derived from the decomposition of alkyl halides, etc Adv. Catal. 42 181-313... [Pg.1795]

By the action of alkyl halides on the silver salt of the acid. [Pg.96]

The preparation of pure primary amines by the interaction of alkyl halides and ammonia is very difficult, because the primary amine which is formed reacts with unchanged alkyl halide to give the secondary amine the latter... [Pg.127]

The following are some of the most important reactions of alkyl halides which will assist in their identification. [Pg.289]

These are readily available from the interaction of alkyl halides with sodium or potas slum oyanide in aqueous alooholic solution (compare Section 111,113). [Pg.354]

The mono-alkyl C-substituted derivatives of ethyl acetoacetate upon treatment with sodium ethoxide and another molecule of alkyl halide afford the di-alkyl C-substituted products... [Pg.476]

Esters are alkylated in the presence of strong bases in aprotic solvents. A common combination is LDA in tetrabydrofuran at low temperatures. Equimolar amounts of base are sufficient and only the mono-carbanion Js formed. After addition of one mole of alkyl halide the products form rapidly, and no dialkylation, which is a problem in the presence of excess base, is possible. Addition of one more mole of LDA and of another alkyl halide leads to asymmetric dialkylation of one or-carbon atom in high yield (R.J. Cregge, 1973). [Pg.22]

Amines are powerful nucleophiles which react under neutral or slightly basic conditions with several electron-accepting carbon reagents. The reaction of alkyl halides with amines is useful for the preparation of tertiary amines or quaternary ammonium salts. The conversion of primary amines into secondary amines is usually not feasible since the secondary amine tends towards further alkylation. [Pg.290]

Oxidative addition of alkyl halides to Pd(0) is slow. Furthermore, alkyl-Pd complexes, formed by the oxidative addition of alkyl halides, undergo facile elimination of /3-hydrogen and the reaction stops at this stage without undergoing insertion or transmetallation. Although not many examples are available, alkynyl iodides react with Pd(0) to form alkynylpalladium complexes. [Pg.127]

The most interesting and difficult cross-coupling is alkyl-alkyl coupling, because oxidative addition of alkyl halides having /i-hydrogen is slow. In addition, easy elimination of /d-hydrogen is expected after the oxidative addition. [Pg.226]

Substitutive nomenclature of alkyl halides treats the halogen as a halo—(fluoro chloro bromo or lodo ) substituent on an alkane chain The carbon chain is numbered m the direction that gives the substituted carbon the lower number... [Pg.144]

For a discussion concerning the boiling point behavior of alkyl halides see the January 1988 issue of the Journal of Chemical Education pp 62-64... [Pg.149]

Preparation of Alkyl Halides from Alcohols and Hydrogen Halides... [Pg.151]

PREPARATION OF ALKYL HALIDES FROM ALCOHOLS AND HYDROGEN HALIDES... [Pg.151]

The procedures to be described m the remainder of this chapter use either an alkane or an alcohol as the starting material for preparing an alkyl halide By knowing how to prepare alkyl halides we can better appreciate the material m later chapters where alkyl halides figure prominently m key chemical transformations The preparation of alkyl halides also serves as a focal point to develop the principles of reaction mechanisms... [Pg.151]

We 11 begin with the preparation of alkyl halides from alcohols by reaction with hydro gen halides... [Pg.152]

Chemical reactivity and functional group transformations involving the preparation of alkyl halides from alcohols and from alkanes are the mam themes of this chapter Although the conversions of an alcohol or an alkane to an alkyl halide are both classi tied as substitutions they proceed by very different mechanisms... [Pg.178]

Dehydrogenation of alkanes is not a practical laboratory synthesis for the vast majority of alkenes The principal methods by which alkenes are prepared m the labo ratory are two other (3 eliminations the dehydration of alcohols and the dehydrohalo genation of alkyl halides A discussion of these two methods makes up the remainder of this chapter... [Pg.202]

This concludes discussion of our second functional group transformation mvolv mg alcohols the first was the conversion of alcohols to alkyl halides (Chapter 4) and the second the conversion of alcohols to alkenes In the remaining sections of the chap ter the conversion of alkyl halides to alkenes by dehydrohalogenation is described... [Pg.211]

Similarly sodium methoxide (NaOCHj) is a suitable base and is used m methyl alco hoi Potassium hydroxide m ethyl alcohol is another base-solvent combination often employed m the dehydrohalogenation of alkyl halides Potassium tert butoxide [K0C(CH3)3] is the preferred base when the alkyl halide is primary it is used m either tert butyl alcohol or dimethyl sulfoxide as solvent... [Pg.212]

The regioselectivity of dehydrohalogenation of alkyl halides follows the Zaitsev rule p elimination predominates m the direction that leads to the more highly substi tuted alkene... [Pg.212]

In addition to being regioselective dehydrohalogenation of alkyl halides is stereo selective and favors formation of the more stable stereoisomer Usually as m the case of 5 bromononane the trans (or E) alkene is formed m greater amounts than its cis (or Z) stereoisomer... [Pg.213]

The rate of elimination depends on the halogen the reactivity of alkyl halides increasing with decreasing strength of the carbon-halogen bond... [Pg.214]

Like alcohol dehydrations El reactions of alkyl halides can be accompanied by carbocation rearrangements Eliminations by the E2 mechanism on the other hand nor mally proceed without rearrangement Consequently if one wishes to prepare an alkene from an alkyl halide conditions favorable to E2 elimination should be chosen In prac tice this simply means carrying out the reaction m the presence of a strong base... [Pg.219]

Dehydrohalogenation of alkyl halides (Sections 5 14-5 16) Strong bases cause a proton and a halide to be lost from adjacent carbons of an alkyl halide to yield an alkene Regioselectivity is in accord with the Zaitsev rule The order of halide reactivity is I > Br > Cl > F A concerted E2 reaction pathway is followed carbocations are not involved and rearrangements do not occur An anti coplanar arrangement of the proton being removed and the halide being lost characterizes the transition state... [Pg.222]

Section 5 15 Dehydrohalogenation of alkyl halides by alkoxide bases is not compli cated by rearrangements because carbocations are not intermediates The mechanism is E2 It is a concerted process m which the base abstracts a proton from the p carbon while the bond between the halogen and the a carbon undergoes heterolytic cleavage... [Pg.223]

Nucleophilic substitution reactions of alkyl halides are related to elimination reactions m that the halogen acts as a leaving group on carbon and is lost as an anion The... [Pg.326]

Representative Functional Group Transformations by Nucleophilic Substitution Reactions of Alkyl Halides... [Pg.328]

The order of alkyl halide reactivity in nucleophilic substitutions is the same as their order m eliminations Iodine has the weakest bond to carbon and iodide is the best leaving group Alkyl iodides are several times more reactive than alkyl bromides and from 50 to 100 times more reactive than alkyl chlorides Fluorine has the strongest bond to car bon and fluonde is the poorest leaving group Alkyl fluorides are rarely used as sub states m nucleophilic substitution because they are several thousand times less reactive than alkyl chlorides... [Pg.330]

The first example of a stereo electronic effect in this text concerned anti elimination in E2 reactions of alkyl halides (Section 5 16)... [Pg.333]


See other pages where Of alkyl halides is mentioned: [Pg.79]    [Pg.6]    [Pg.227]    [Pg.261]    [Pg.144]    [Pg.149]    [Pg.178]    [Pg.211]    [Pg.211]    [Pg.213]    [Pg.214]    [Pg.215]    [Pg.216]    [Pg.217]    [Pg.217]    [Pg.219]    [Pg.329]   
See also in sourсe #XX -- [ Pg.17 , Pg.18 , Pg.19 ]

See also in sourсe #XX -- [ Pg.565 ]

See also in sourсe #XX -- [ Pg.76 ]

See also in sourсe #XX -- [ Pg.95 , Pg.97 , Pg.99 , Pg.350 , Pg.378 , Pg.379 , Pg.425 , Pg.426 ]




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Action of Dimethyl Sulphate on Magnesium Alkyl or Aryl Halide (Grignard)

Activation of alkyl halides

Addition of alkyl halides

Alcohols by hydrolysis of alkyl halides

Alkene Synthesis by Elimination of Alkyl Halides

Alkyl and Acyl Halides with the Sodio-derivatives of Ethyl Cyanoacetate

Alkyl halides formation of esters

Alkyl halides in Gabriel synthesis of amines

Alkyl halides table of and derivatives

Alkyl halides, dehydrohalogenation summary of chemistry

Alkylation of Alkenes with Organic Halides

Alkylation of Amines by Alkyl Halides

Alkylation of Pyrroles with Allyl Halides

Alkylation of Pyrroles with Propargyl Halides

Alkylation of alkyl halides

Alkylation of aryl halides

Analysis of alkyl halides

And elimination of alkyl halides

Base-Promoted Elimination of an Alkyl Halide

Boiling points of alkyl halides

Bond of alkyl halides

By reduction of alkyl halides

Carbocations as intermediates in reactions of alkyl halides

Carbonylation of Alkyl Halides (Pd, Rh)

Carbonylation, of alkyl halides

Classes of Alcohols and Alkyl Halides

Common Uses of Alkyl Halides

Conversion of Alcohols to Alkyl Halides with HX

Conversion of Alcohols to Alkyl Halides with SOCI2 and PBr

Coupling of alkyl halides

Coupling of alkyl halides with organometallic compounds

Cyclization of alkyl halides

Dehalogenation, of alkyl halides

Dehydrohalogenation of alkyl halides

Diastereoselective Alkylation of Glycine Schiff Base with Optically Enriched Alkyl Halides

Dipole moment of alkyl halides

Direct Oxidative Addition of Reactive Zinc to Functionalized Alkyl, Aryl, and Vinyl Halides

E2 Elimination of an Alkyl Halide

Elimination Reactions by Sml2 Reduction of Alkyl Halides

Elimination Reactions of Alkyl Halides Zaitsevs Rule

Elimination Reactions of Alkyl and Alkenyl Halides

Elimination of Alternate Non-Terminal Alkyl Halides

Elimination of HX (X F, Cl, Br, I) from Alkyl and Alkenyl Halides

Elimination of alkyl halides

Elimination reactions of alkyl halides

Enzyme-Catalyzed Nucleophilic Substitutions of Alkyl Halides

Formation of Alkyl Halides

From reduction of alkyl halides

Functional class nomenclature of alkyl halides

Heck-type Reaction of Alkyl Halides with Styrenes

Hydrodehalogenation of alkyl halides

Hydrogenolysis of alkyl halides

Hydrolysis of alkyl halides

I Reactions of Alkyl Halides Nucleophilic Substitutions and Eliminations

In tnfluoroacetic acid of alkyl halides by Nphenyltnflamide

Iron, pentacarbonylcatalyst carbonylation of alkyl and aralkyl halides

Iron-Catalyzed Arylations of Alkyl (Pseudo) Halides

Magnesium reaction of with alkyl and aryl halide

Mass spectrometry of alkyl halides

Methylation of Secondary Alkyl Halides

NAMING OF ALKYL HALIDES

Names and Properties of Alkyl Halides

Names and Structures of Alkyl Halides

Nitration of alkyl halides

Nomenclature of alkyl halides

Nucleophilic Aliphatic Substitution Preparation of Alkyl Halides

Nucleophilic substitution reactions of alkyl halides

Of alkyl halides to alkanes

Oxidative Addition and Reductive Elimination of Alkyl Halides

Oxidative addition of alkyl halides

PROPERTIES OF ALKYL HALIDES

Photobehavior of Alkyl Halides

Physical Properties of Alcohols and Alkyl Halides Intermolecular Forces

Physical properties of alkyl halides

Preparation of Alkyl Halides

Preparation of Alkyl and Aryl Halides

Propargylation, of alkyl halides

REACTIONS OF ALKYL HALIDES

REDUCTION OF ALKYL HALIDES AND

REDUCTION OF ALKYL HALIDES AND TOSYLATES WITH SODIUM CYANOBOROHYDRIDE

Reaction CXIX.—Action of Silver Nitrite on Alkyl Halides

Reaction CXXV.—Action of Alkyl Halides on Phthalimide (Potassium Salt)

Reaction XIV.—(a) Action of Magnesium Alkyl or Aryl Halide on Aldehydes and Ketones (Grignard)

Reaction of Alkyl, Alkenyl, and Aryl Halides with Metals

Reaction of Amines with Alkyl Halides

Reaction of Lithiated Bis(methylthio)methane with Alkyl Halides

Reaction of alkyl halides with sulfites and sulfinic acids

Reaction of stabilized carbanions (enolates) with alkyl halides (enolate alkylation)

Reactions of Alkyl Halides Grignard Reagents

Reactions of Alkyl Halides Nucleophilic Substitutions and Eliminations

Reactions of Alkyl Halides Substitution and Elimination

Reactions of Alkyl Halides The Substitution Reaction

Reactivities of Some Alkyl Halides

Rearrangement Reactions of Alkyl and Alkenyl Halides

Reduction of Alkyl, Alkenyl, and Aryl Halides

Reduction of alkyl halides

Reductive elimination of alkyl halides

Regioselectivity dehydrohalogenation of alkyl halides

Retention alkylation of vinylic halides

SYNTHESIS OF ALCOHOLS FROM ALKYL HALIDES

SYNTHESIS OF ALKYL HALIDES

Silane, a-phenylthiomethyltrimethylreaction with alkyl halides synthesis of aldehydes

Silver cyanide, reaction with alkyl halides in synthesis of isocyanides

Sn2 reaction of alkyl halides

Sn2 substitution reactions conversion of alcohols to alkyl halides

SnI reaction of alkyl halides

Sodium tetracarbonylcobaltate carbonylation of alkyl halides

Sodium tetracarbonylferrate carbonylation of alkyl and aralkyl halides

Solvolysis of alkyl halides

Stereoselective reactions dehydrohalogenation of alkyl halides

Structure of Alkyl Halides

Substitution reactions of alkyl halides

Summary of Alkyl Halide Chemistry

The Nomenclature of Alkyl Halides

The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines

The Structures of Alkyl Halides, Alcohols, Ethers, and Amines

Transfer of Carbamate Group to Alkyl Halides

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