Consider the general substitution-elimination reactions of the bromoalkanes.

How do the reaction mechanisms and product formation differ when the structure of the substrate and reaction conditions change? To begin to unravel the nuances of bimolecular and unimolecular substitution and elimination reactions, focus on the treatment of bromoalkanes A through D under conditions (a) through (e). Divide the problem evenly among yourselves so that each of you tackles the questions of reaction mechanism(s) and qualitative distribution of product(s), if any. Reconvene to discuss your conclusions and come to a consensus. When you are explaining a reaction mechanism to the rest of the team, use curved arrows to show the flow of electrons. Label the stereochemistry of starting materials and products as R or S, as appropriate.

(a) NaN₃, DMF

(b) LDA, DMF

(c) NaOH, DMF

(d)

(e) CH₃OH

Transcribed Image Text:

Nu/base R-Br R-Nu + alkene