The Contrasting Alkylations of 4-(Dimethylaminomethyl)pyridine and 4-(Dimethylamino)pyridine: An Organic Chemistry Experiment

A critical factor for the increased nucleophilicity of the pyridine nitrogen in 4-(dimethylamino)pyridine (DMAP) is electron donation via resonance from the amino group into the aromatic ring that increases electron density on the pyridine nitrogen. To explore how important this resonance effect is, 4-(dimethylaminomethyl)pyridine (DMAMP) was synthesized and the alkylation products of DMAP and DMAMP were compared. The methylene group between the pyridine ring and the amino group in DMAMP removes the possibility of resonance effects between the two nitrogen atoms. Alkylation of DMAP occurs exclusively at the pyridine nitrogen, whereas alkylation of DMAMP occurs exclusively at the amino group indicating that resonance effects are quite important. When these alkylations are carried out with a 1:1 equimolar ratio of CH3I and CH3CH2I, only methylated products are formed. This laboratory experiment is designed to teach students how to analyze the fundamental concepts of nucleophilicity and electrophilicity as a method of accurately predicting the reactivity of organic compounds. Molecular orbital calculations are used to examine the electron density present on each nitrogen atom of DMAP and DMAMP (as a measure of nucleophilicity) and to determine the stability of the possible products

A comparison of rapid cycle deliberate practice and traditional reflective debriefing on interprofessional team performance

Abstract Background In simulation-based education, debriefing is necessary to promote knowledge acquisition and skill application. Rapid Cycle Deliberate Practice (RCDP) and Traditional Reflective Debriefing (TRD) are based in learning theories of deliberate practice and reflective learning, respectively. In this study, we compared the effectiveness of TRD versus RCDP on acquisition of conceptual knowledge and teamwork skills among interdisciplinary learners in the pediatric emergency department. Methods One hundred sixty-four learners including emergency department attending physicians, fellows, nurses, medical technicians, paramedics, and respiratory therapists, participated in 28 in-situ simulation workshops over 2 months. Groups were quasi-randomized to receive RCDP or TRD debriefing. Learners completed a multiple-choice test to assess teamwork knowledge. The TEAM Assessment Tool assessed team performance before and after debriefing. Primary outcomes were teamwork knowledge and team performance. Results Average pre-intervention baseline knowledge assessment scores were high in both groups (TRD mean 90.5 (SD 12.7), RCDP mean 88.7 (SD 15.5). Post-test scores showed small improvements in both groups (TRD mean 93.2 (SD 12.2), RCDP mean 89.9 (SD 13.8), as indicated by effect sizes (ES = 0.21 and 0.09, for TRD and RCDP, respectively). Assessment of team performance demonstrated a significant improvement in mean scores from pre-assessment to post-assessment for all TEAM Assessment skills in both TRD and RCDP arms, based on p-values (all p  0.8). While pre-post improvements in TEAM scores were generally higher in the RCDP group based on effect sizes, analysis did not indicate either debriefing approach as meaningfully improved over the other. Conclusions Our study did not demonstrate that either TRD versus RCDP was meaningfully better in teamwork knowledge acquisition or improving skill application and performance. As such, we propose Reflective Deliberate Practice as a framework for future study to allow learners to reflect on learning and practice in action

Additional file 1 of A comparison of rapid cycle deliberate practice and traditional reflective debriefing on interprofessional team performance

Additional file 1: Table S1. Simulation scenario and learning objectives