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18 Cards in this Set
- Front
- Back
Substitution
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Occur when one functional group replaces another.
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Sn1 reaction
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Two step reaction with a rate dependent on only one of the reactants.
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Slow step
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Rate determining step of reaction
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Sn2 reaction
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One step reaction with a rate dependent on the concentration of the nucleophile and the substrate
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Sterical Hinderance
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Sn2 reactions typically do not occur in tertiary substrates.
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"The nucleophile and the 5 Ss"
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Differences between Sn1 and Sn2 reactions
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"The Nucleophile"
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Sn2 requires strong nucleophile while Sn1 is not affected by nucleophile strength
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1st S- Substrate
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Sn2 reactions dont occur with sterically hindered substrate. Sn2 requires methyl, primary or secondary substrate while Sn2 requires secondary or tertiary.
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2nd S- Solvent
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Highly polar solvent increases reaction rate of Sn1 by stabilizing the carbocation, but slows down Sn2 reactions by stabilizing the nucleophile
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3rd S- Speed
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Speed of Sn2 depends on concentration of substrate and the nucleophile, while speed of Sn1 depends only on the substrate.
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4th S- Stereochemistry
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Sn2 inverts stereochemistry about chiral center while Sn1 creates a racemic mixture.
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5th S- Skeleton
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Sn1 may be accompanied by carbon skeleton rearrangement but Sn2 never rearranges the carbon skeleton.
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Oxidation
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Loss of H2, addition of O or O2, addition of X2
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Reduction
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Addition of H2, loss of O or O2, loss of X2
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Formation of sulfonates
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Nucleophilic substitution where alcohol acts as a nucleophile.
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Tosylates and mesylates
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commonly used sulfonates (draw)
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Pinacol arrangement
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Dehydration of an alcohol that results in a unexpected product
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Ethers
yj |
Polar, relatively non reactive substances that can hydrogen bond with compounds that contain hydrogen attached to an N, O, or F atom.
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