Chapter 7 Discussion Worksheet
Mechanisms of SN1 and SN2 Substitutions
1. Circle any substrates that would require an initial proton transfer in an Sn1 reaction. (Problem 7.18)
2. Circle any nucleophiles that would require a proton transfer at the end of an Sn1 reaction. (Problem
7.19)
NaSH H2S H2O EtOH NaCN NaCl NaNH2 NH3 NaOMe NaOEt MeOH KBr
3. Four sequential Sn2 reactions can account for this transformation. Draw a full mechanism for the
reaction (Problem 7.25)
4. Below are two potential methods for preparing the same ether, but only one of them is successful.
Identify the successful approach and explain your choice. (Problem 7.62)
5. Provide the necessary reagents. (Problem 7.63)
Cyclobutanol  bromocyclobutane
tert-butanol  tert-butylchloride
ethyl chloride  ethanol
6. Draw mechanisms for these Sn1 reactions and then identify the pattern of steps. Problems 21, 27,
67--Problems 7.21 and 7.22 for more practice)