Chem 215

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8 Terms

1
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oxidation of alcohols

primary alcohol → aldehyde → hydrate → carboxylic acid (under wet conditions, in dry stops at aldehyde)

secondary alcohol → ketone (always)

tertiary alcohol → not responsive to oxidation

2
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Jones reagent (wet Cr6+)

CrO3, H2O, H2SO4 → H2CrO4 (chromic acid)

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dry Cr6+

CrO3 + 2 equiv. of pyridine

PCC (pyridinium chlorochromate) = protonated pyridine + ClCrO3-

PDC (pyridinium dichromate) = 2 equiv. protonated pyridine + Cr2O72-

4
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swern oxidation

  1. dimethiyl sulfoxide O=S-(CH3)2 + oxalyl chloride C2O2Cl2

  2. Base: triethylamine N(CH2CH3)3

5
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good electron donors

anion, uncharged N, P, S, hindered bases (do SN2/E2)

6
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poor electron donors

lack qualities of good electron donors (do NOT do SN2/E2, can potentially do SN1/E1)

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nucleophile

donates electrons

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electrophile

accepts electrons

have the leaving group on them