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Alkyl chlorides are versatile building blocks in organic chemistry. While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles. Heating alkyl halides with sodium hydroxide or water gives alcohols.
The classic Finkelstein reaction entails the conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by treatment with a solution of sodium iodide in acetone. Sodium iodide is soluble in acetone while sodium chloride and sodium bromide are not; [ 3 ] therefore, the reaction is driven toward products by mass action due to the ...
Allyl chloride is the organic compound with the formula C H 2 =CHCH 2 Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin , used in the production of plastics.
Methyl, ethyl, and other alkyl or aralkyl halides that are not dehydrohalogenated readily can react with aluminium in an exothermic process to form organoaluminium sesquihalides in high yields. An important example is the reaction of ethyl chloride with aluminium to form ethylaluminium sesquichloride. 3 C 2 H 5 Cl + 2 Al → (C 2 H 5) 3 Al 2 Cl 3
The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. [1] Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution. [2] [3] [4] [5]
However, if an unreactive alkylating agent is used (e.g. an alkyl chloride) then the rate of reaction can be greatly improved by the addition of a catalytic quantity of a soluble iodide salt (which undergoes halide exchange with the chloride to yield a much more reactive iodide, a variant of the Finkelstein reaction).
Typically these reactions would be conducted in the presence of a base which serves to absorb the HCl. Alkyl chloroformate esters degrate to give the alkyl chloride, with retention of configuration: ROC(O)Cl ' → RCl + CO 2. The reaction is proposed to proceed via a substitution nucleophilic internal mechanism. [3]
The Suárez modification of the Hofmann–Löffler–Freytag reaction was the basis of the new synthetic method developed by H. Togo et al. [42] [43] The authors demonstrated that various N-alkylsaccharins (N-alkyl-1,2-benzisothiazoline-3-one-1,1,-dioxides) 77 are easily prepared in moderate to good yields by the reaction of N-alkyl(o-methyl ...