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19 Nov 2019
what is the reaction to this experiment?
not the mechanism.
19 EXPERIMENT ALKYLATION OF THE AMINO GROUP USING THE ESCHWEILER CLARK METHYLATION PROCEDURE In this experiment a primary amine will be converted into a tertiary amine using the Eschweiler-Clark methy lation reaction. The procedure presented herein is a modified procedure from a report in the Journal of Chemical Education that appeared in 1968. Download this article from http/pubs acs org (from the USM net work) and read it prior to coming to lab. Notice that the scale that was originally utilized is quite large com pared to the procedure reported herein The amino functional group can serve as a good nucleophile in typical Sy2 type reactions with alkyl halides Unfortunately, the amino group has a habit of over-alkylating ultimately giving quaternary ammonium sa as a significant product. This is of course perfectly fine if the chemist wishes to prepare quaternary ammo nium salts However, it is frequently the case that tertiary amines are the desired product and having the reac tion stop at the tertiary amine typically proves quite difficult under typical Sy2 conditions. Scheme ilustrates the problem inherent in the alkylation of amines using alkyl halides as alkylating agents lts 19.1 Pine, S. H.J.Chem. Educ. 1968, 45, 118 109
what is the reaction to this experiment?
not the mechanism.
19 EXPERIMENT ALKYLATION OF THE AMINO GROUP USING THE ESCHWEILER CLARK METHYLATION PROCEDURE In this experiment a primary amine will be converted into a tertiary amine using the Eschweiler-Clark methy lation reaction. The procedure presented herein is a modified procedure from a report in the Journal of Chemical Education that appeared in 1968. Download this article from http/pubs acs org (from the USM net work) and read it prior to coming to lab. Notice that the scale that was originally utilized is quite large com pared to the procedure reported herein The amino functional group can serve as a good nucleophile in typical Sy2 type reactions with alkyl halides Unfortunately, the amino group has a habit of over-alkylating ultimately giving quaternary ammonium sa as a significant product. This is of course perfectly fine if the chemist wishes to prepare quaternary ammo nium salts However, it is frequently the case that tertiary amines are the desired product and having the reac tion stop at the tertiary amine typically proves quite difficult under typical Sy2 conditions. Scheme ilustrates the problem inherent in the alkylation of amines using alkyl halides as alkylating agents lts 19.1 Pine, S. H.J.Chem. Educ. 1968, 45, 118 109
Lelia LubowitzLv2
28 Apr 2019