7. Substitution Reactions
Substitution Comparison
68PRACTICE PROBLEM
Consider the following reaction:
1-chloro-1,3,4-trimethylcyclopentane + propan-1-ol →
Is its mechanism predominantly first order (SN1) or second order (SN2)? What is the expected substitution product? (Recall: The strength of the nucleophile (or base) usually dictates the order of the reaction. Weak nucleophiles often react by unimolecular first-order pathways, while strong nucleophiles promote bimolecular second-order reactions. Also, SN1 is unlikely with 1° halides unless they are resonance-stabilized, while SN2 is unlikely with 3° halides.)
Consider the following reaction:
1-chloro-1,3,4-trimethylcyclopentane + propan-1-ol →
Is its mechanism predominantly first order (SN1) or second order (SN2)? What is the expected substitution product? (Recall: The strength of the nucleophile (or base) usually dictates the order of the reaction. Weak nucleophiles often react by unimolecular first-order pathways, while strong nucleophiles promote bimolecular second-order reactions. Also, SN1 is unlikely with 1° halides unless they are resonance-stabilized, while SN2 is unlikely with 3° halides.)