Chloromethane sodium hydroxide reaction

A purified form of cellulose, obtained from cotton linters or wood pulp, is reacted with sodium hydroxide solution to produce a swollen alkali cellulose that is chemically more reactive than untreated cellulose. The alkali cellulose is then treated with chloromethane and propylene oxide to produce methyl hydroxypropyl ethers of cellulose. The fibrous reaction product is then purified and ground to a fine, uniform powder or granules. 

Although chloromethane is not highly soluble in water, it is soluble enough to carry out our kinetic study in an aqueous solution of sodium hydroxide. Because reaction rates are known to be temperature dependent (Section 6.7), we carry out the reaction at a constant temperature. 

Chlorine and sodium hydroxide are the main products of the industrial chlor-alkali electrolysis that is described as a process example in Section 6.19. Hydrochloric acid is produced by reaction from the elements H2 and CI2 or by the reaction of chloride salts such as, for example, NaCl or CaCl2, with sulfuric acid. Other important sources of HCl are industrial chlorination processes using CI2 as chlorination agent (e.g., chlorination of benzene to form chlorobenzene and HCl or the chlorination of methane to give chloromethane and HCl) or industrial dehydrochlorination processes (e.g., production of vinyl chloride and HCl from 1,2-dichloroethane). The main uses of hydrochloric acid are addition reactions to unsaturated compounds (by hydrochlorination or oxychlorination), formation of chlorine in the Deacon process, production of chloride salts from amines and other organic bases, dissolution of metals, regeneration of ion exchange resins, and the neutralization of alkaline products. 

Substitutions are the characteristic reactions of saturated compounds such as alkanes and alkyl halides and of aromatic compounds (even though they are unsaturated). In a substitution, one group replaces another. For example, chloromethane reacts with sodium hydroxide to produce methyl alcohol and sodium chloride ... 

Let us now consider another mechanism for nucleophilic substitution the SnI reaction. When tert-butyl chloride reacts with sodium hydroxide in a mixture of water and acetone, the kinetic results are quite different than for the reaction of chloromethane with hydroxide. The rate of formation of tert-butyl alcohol is dependent on the concentration of tert-butyl chloride, but it is independent of the concentration of hydroxide ion. Doubling the tert-butyl chloride concentration doubles the rate of the substitution reaction, but changing the hydroxide ion concentta-tion (within limits) has no appreciable effect tert-Butyl chloride reacts by substitution at virtually the same rate in pure water (where the hydroxide ion is 10 M) as it does in 0.05M aqueous sodium hydroxide (where the hydroxide ion concentration is 500,000 times larger). (We shall see in Section 6.10 that the important nucleophile in this reaction is a molecule of water.)... 

Many processes in organic chemistry exhibit characteristics of acid-base reactions. For example, heating an aqueous mixture of sodium hydroxide and chloromethane, CH3CI, produces methanol and sodium chloride. As noted in Section 2-2, this process involves the same kind of movement of two pairs of electrons as does the acid-base reaction between sodium hydroxide and HCl ... 

One of the most powerful techniques employed by chemists is the measurement of the kinetics of the reaction (Section 2-1). By comparing the rate of product formation beginning with several different concentrations of the starting materials, we can establish the rate equation, or rate law, for a chemical process. Let us see what this experiment teUs us about the reaction of chloromethane with sodium hydroxide. 

The reaction of chloromethane with sodium hydroxide is bimolecular... 

We can monitor rates by measuring either the disappearance of one of the reactants or the appearance of one of the products. When we apply this method to the reaction of chloromethane with sodium hydroxide, we find that the rate depends on the initial concentrations of both of the reagents. For example, doubling the concentration of hydroxide doubles the rate at which the reaction proceeds. Likewise, at a fixed hydroxide concentration, doubling the concentration of chloromethane has the same effect. Doubling the concentrations of both increases the rate by a factor of 4. These results are consistent with a second-order process (Section 2-1), which is governed by the following rate equation ... 

Chloromethane reacts in a substitution reaction with sodium hydroxide in aqueous solution to produce methanol and sodium chloride. Write the equilibrium constant expression for this substitution reaction. The equilibrium constant is 5 X 10. Is the reaction quantitative ... 

Let us inspect these transformations in greater detail. In reaction 1, a hydroxide ion, typically derived from sodium or potassium hydroxide, displaces chloride from chloromethane to give methanol. This substitution is a general synthetic method for converting a methyl or primary haloalkane into an alcohol. 

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