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21 Cards in this Set
- Front
- Back
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Radical reactions
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abstract a hydrogen.
3>2>1 |
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Hindered Bases
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K Ot Bu
(potassium tertbutoxide) Only performs elimination |
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strong bases
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Na OEt
1*= SN2 too strong of base for 2 and 3. will pull off hyrdrogens before it gets to compound. |
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weak base
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RCOO(-), CN(-)
SN2 for 1 and 2. SN1 and E1 for 3. |
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alkoxy derivatives
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use an oxygen bridge to substituent. "Ch3-O-" methoxy
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cyclic ethers
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"oxa" indicates presence
oxacyclohexane. |
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diol preperation
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OsO4 (cis addition of 2 oh groups)
RCOOOH (peroxyacid - trans) internal double bond |
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acid catalyzed hydration
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hydrates markovnikov.
be aware of rearrangements. forms alcohol. |
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Alcohol properties
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weak acids. react with alkali metals and strong bases (NaOEt)
use HBr to make alkyl hallides |
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Ethers
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Williamson synthesis
(R-Alcohol + NaH --> + R-Br = ROR) Reacts with alkyl hallides (cold= ROH RX, hot=RX, RX) |
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epoxides
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cyclic ethers
prepaired with MMPP on double bonds. adding acid produces a diol. |
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crown ethers
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phase transfer catalysts
18 crown 6 - K+ |
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oxidation
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1 alcohol --PCC---> ketone
1 alcohol ---KMnO4---> carboxylic acid 2 alcohol---HCrO4---> ketone 3* hard to oxidize |
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reduction
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anything---Li Al H4--->alcohol
aldehyde/ketone--NaBH4-->alcohol |
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Li & grignard
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prganometallic with partial charge
made in ether. makes R group powerful base/nucleophile. careful with acidic Hs. |
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Li & grignard & all alcohols
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R-Li+ formaldehyde= R-primary alcohol
R-Li+aldehyde=R-secondary alcohol R-Li+ketone=r-tertiary alcohol R-Li+ester=ketone |
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sodium alkydes
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R-C(tripple)C-Na+ also react the same as Li & grignard
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R2-Cu-Li
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R2 groups are the same. coupling agent. R2CuLi+ R-X = R-R
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allylic bromination
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NBS
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alkadienes
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have 2 double bonds. if double-single-double- conjugated. resonating allyl cation will produce 2 products
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kinetic vs thermodynamic control
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Mild conditions -kinetic- (0*c) (1,2 product)
rigirous - thermodynamic(40*c) (1,4 product) |
