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How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism:...

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How we do we determine whether a reaction is SN1 or SN2? Factor #1: Electrophile (substrate). Is the electrophile primary, secondary, or tertiary? LG = Leaving Group

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Page 1: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

How we do we determine whether a reaction is SN1 or SN2? Factor #1: Electrophile (substrate). Is the electrophile primary, secondary, or tertiary? LG = Leaving Group

Page 2: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

Page 3: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

Page 4: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

Page 5: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

Factor #2: The Nucleophile

Strong Nucleophiles favor SN2; Weak Nucleophile disfavors SN2 thereby allowing SN1 to compete

Page 6: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

Factor 3: Leaving Group Good leaving groups are typically the conjugate bases of strong acids. In other words, the weaker the basicity of a leaving group, the greater the leaving group.

Page 7: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

Page 8: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

Factor 4: The Solvent Common solvents used in organic chemistry (for now, only focus on the highlighted):

Page 9: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

Using all four factors:

Page 10: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

Page 11: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

Page 12: How we do we determine whether a reaction is SN1 or SN2? … · 2019. 7. 17. · SNI mechanism: Predict whether the reaction below will occur via an SN2 or an DMSO Answer This reaction

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