Ethene with hydrogen chloride

Methylpropene reacts with ethene and hydrogen chloride under polar conditions to yield 1-chloro-3,3-dimethylbutane. Show a mechanism for this reaction that is consistent with the reactants, conditions, and product. Give your reasoning. 

DIFLUOROETHENE or DIFLUORO-l,l-ETHENE (75-38-7) Flammable gas (flash point <—85°F/<—65°C). Violent reaction with oxidizers, barium, sodium, or potassium. Reacts with aluminum chloride. Incompatible with hydrogen chloride. May form explosive compounds with light metals and metallic azides. Capable of forming unstable peroxides may cause explosive polymerization. Undergoes thermal decomposition when exposed to flame or red-hot surfaces. May accumulate static electricity, and cause ignition of its vapors. The uninhibited monomer vapor may block vents and confined spaces by forming a solid polymer material. 

Hydrogen halides (HCl, HBr, etc.) react with alkenes to produce halogenoalkanes. These reactions take place rapidly in solution at room temperature. For example, ethene reacts with hydrogen chloride to form chloroethane, and but-Z-ene reacts with hydrogen bromide to form Z-bromobutane ... 

Industrially it is produced by the chlorination of ethene, either by the direct chlorination process using chlorine or by the oxychlorination with hydrogen chloride as... 

In the oxychlorination process ethene and hydrogen chloride are reacted with oxygen in the presence of a catalyst, which consists in most cases of copper salts, the temperatures usually are above 200 °C. 

Alkenes can also add unsymmetrical reagents across the double bond. For example, ethene reacts with hydrogen chloride to form chloroethane. 

The entropy change AS0 for the formation of chloroethane by chlorination of ethane is +0.5 e.u., and for the formation of chloroethane by combination of hydrogen chloride with ethene AS0 is —31 e.u. Explain. 

In Section 10-5 we showed that ethyne is much less reactive toward chlorine than is ethene. The same is true for hydrogen chloride. Flowever, when hydrogen chloride adds to 3-butenyne, it adds to the triple bond instead of the double bond, thereby forming 2-chloro-1,3-butadiene instead of 3-chloro-1-butyne. With reference to the discussion in Section 13-2, explain why the order of reactivity of the double and triple bonds of 3-butenyne toward electrophilic reagents may be different from that of ethene and ethyne ... 

The most economical commercial preparation is high-temperature chlorination of ethene. A useful modification of this process uses hydrogen chloride in place of chlorine. An oxidizing agent is required to raise the oxidation state of chlorine in HC1 to that of Cl2 molecular oxygen is used for this purpose along with cupric salts as catalysts. 

Methyl />-tolyl sulfone has been prepared by oxidation of methyl 7>-tolyl sulfide with hydrogen peroxide 4 r or ruthenium tetroxide,6 by alkylation of sodium -toluenesullinate with methyl iodide 7,8 or with methyl potassium sulfate,9 by decarboxylation of -tolylsulfonylacetic acid,7 by thermal decomposition of tetramethylammonium -toluenesulfinate,10 by reaction of cw-bis-(%tolylsulfonvl)-ethene with sodium hydroxide (low yield),11 by the reaction of methanesulfonyl chloride with toluene in the presence of aluminum chloride (mixture of isomers),12 by... 

Synonyms Chlorinated polyethylene Chloroethene, compd. with ethene CPE Classification Olefin Properties Wh. gran. dens. 1.220 Toxicology May be harmful by inh., ing., or skin absorption may cause skin/eye irritation Precaution May dec. under fire conditions to form flamm./explosive mixts. in air Hazardous Decomp. Prods. CO, CO2, hydrogen chloride gas Uses Infoodpkg. 

Scheme 6.53. The reaction of chlorine (CI2) with ethene (ethylene, H2C=CH2) to produce 1,2-dichloroethane (CIH2CCH2CI) followed by elimination of hydrogen chloride (HCl) from a different rotational conformer in either a iy -coplanar (or cis or suprafacial) or an anti-coplanar (or trans or antarafacial) sense to produce chloroethene [C1(H)C=CH2].

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