Química Orgánica II
PhD. Tatiana Sarmiento Monsalve
PhD. Diana Vargas Oviedo
Workshop Nucleophilic Substitution (SN1 or SN2)
1. Make a comparison table between the reaction mechanism SN1 and SN2, take into account the
reaction order, nature of the substrates, solvents used, nature of the nucleophile, stereochemistry,
kinetics, and other characteristics that you consider relevant.
2. Classify each reaction as a nucleophilic substitution, or elimination reaction. Identify the leaving
group and the nucleophile.
3. For each pair of compounds, indicate which compound is the best SN2 substrate.
a) 2-methyl-1-iodopropane or tert-butyl iodide
(b) cyclohexyl bromide or 1-bromo-1-methylcyclohexane
(c) 2-bromobutane or isopropyl bromide
(d) 1-chloro-2 2 -dimethylbutane or 2-chlorobutane
(e) 1-iodobutane or 2-iodopropane
4. Indicate for each of the following reactions which substitution mechanism is most likely SN1 or
SN2.
