sn2 and sn1

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A) Rate of expression Sn2: r=k[Rx][Nu-] Sn1: r=k[Rx] because there is only one molecule (unimolecular) B) Reaction Intermediate Sn2: Transition state (5 things attached) Sn1: Carbocation, positively charged carbon. C) Stereochemistry Sn2: Inversion Sn1: You get a racemic mixture therefore it doesn't bend light in the polarimeter. 50% retention + 50% inversion= No bending D) Relative Rates of 1 Sn2: primary >secondary, no tertiary Sn1: tertiary > secondary, no primary E) Effect of increasing concentration of nucleophile Sn2: Increased rate of reaction Sn1: No effect F) Effect of increasing concentration of alkyl halide Sn2: rate increases Sn1: [Rx] increases, r increases G) Effect of an ionic or polar solvent Sn2: Bad. Sn1: It is good because the halide can dissolve. H) Effect of a nonpolar solvent Sn2: Yummy. Likes nonpolar solvents because of no stinkin' ions. Sn1: It is bad because the halide is not going to dissolve. I) Effect of bulky groups around reaction center Sn2: Bad. Tertiary is bad because it's in the way. Sn1: it is better because it is more stable and doesn't have to sneak in. You want a more stable tertiary chirocarbon.

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Page 1: Sn2 and sn1

A) Rate of expression Sn2: r=k[Rx][Nu-] •Sn1: r=k[Rx] because there is only one molecule (unimolecular) •

B) Reaction Intermediate Sn2: Transition state (5 things attached) •Sn1: Carbocation, positively charged carbon. •

C) Stereochemistry Sn2: Inversion •Sn1: You get a racemic mixture therefore it doesn't bend light in the polarimeter. •

50% retention + 50% inversion= No bending ‣

D) Relative Rates of 1 Sn2: primary >secondary, no tertiary •Sn1: tertiary > secondary, no primary •

E) Effect of increasing concentration of nucleophile Sn2: Increased rate of reaction •Sn1: No effect •

F) Effect of increasing concentration of alkyl halide Sn2: rate increases •Sn1: [Rx] increases, r increases •

G) Effect of an ionic or polar solvent Sn2: Bad. •Sn1: It is good because the halide can dissolve. •

H) Effect of a nonpolar solvent Sn2: Yummy. Likes nonpolar solvents because of no stinkin' ions. •Sn1: It is bad because the halide is not going to dissolve. •

I) Effect of bulky groups around reaction center Sn2: Bad. Tertiary is bad because it's in the way. •Sn1: it is better because it is more stable and doesn't have to sneak in. You want a more stable tertiary •chirocarbon.

Page 2: Sn2 and sn1

J) Strength of Nucleophile Sn2: Stronger nucleophile is better. More electronegative so it wants to leave. •Sn1: The weaker the better. •