how to tell which mechanism is in action

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4 Terms

1
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carbocation stability

unstable C+ (1st degree and not res. stabilized), then Sn2

stable C+ (3rd degree/benzylic/allylic) then Sn1

2
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strength of Nu and LG ability

strong base (good Nu) favors Sn2

weak base (good LG) favors SN1

3
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solvent effects

polar aprotic solvents (lacks H-bond donor) Sn2 is favored

4
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examples of polar solvents

dimethylsulfoxide, dimethylformamide, MeCN, acetonitrile