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Indicative of its high reactivity (relative to alkyl chlorides), benzyl chloride slowly reacts with water in a hydrolysis reaction to form benzyl alcohol and hydrochloric acid. In contact with mucous membranes, hydrolysis produces hydrochloric acid. Thus, benzyl chloride is a lachrymator and has been used in chemical warfare. It is also very ...
The name "Schotten–Baumann reaction conditions" often indicate the use of a two-phase solvent system, consisting of water and an organic solvent. The base within the water phase neutralizes the acid, generated in the reaction, while the starting materials and product remain in the organic phase, often dichloromethane or diethyl ether .
Reaction with carboxylic acids to form mixed anhydrides: ROC(O)Cl + HO 2 CR' → ROC(O)−OC(O)R' + HCl. 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
Menshutkin-reaction. The reaction is the method of choice for the preparation of quaternary ammonium salts. [1] Some phase transfer catalysts (PTC) can be prepared according to the Menshutkin reaction, for instance the synthesis of triethyl benzyl ammonium chloride (TEBA) from triethylamine and benzyl chloride: Menshutkin reaction
The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines. The reaction is an example of reductive amination. [1] The reaction, named after Rudolf Leuckart, uses either ammonium formate or formamide as the nitrogen donor and reducing agent. It requires high temperatures, usually between 120 and 130 °C; for the ...
The benzyl alcohol thus formed is quickly converted to the chloride under the reaction conditions. Mechanism of Blanc chloromethylation. Other possibilities for the electrophile include (chloromethyl)oxonium cation (ClH 2 C–OH 2 +) or chlorocarbenium cation (ClCH 2 +), which may be formed in the presence of zinc chloride. [4]
The Mannich reaction starts with the nucleophilic addition of an amine to a carbonyl group followed by dehydration to the Schiff base. The Schiff base is an electrophile which reacts in a second step in an electrophilic addition with an enol formed from a carbonyl compound containing an acidic alpha-proton.
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 ...