Term
| Acid-Base Properties of Alcohols |
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Definition
Alkloxonium ions
(H+)
ROH
(B- (base))
Alkoxide |
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Definition
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Term
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Definition
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Term
| Nucleophilic displacement of Halides and Other leavying groups by hydroxide : |
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Definition
| RCH2CX + HO- goes to RCH2 OH + X- through water and Sn2 rxn |
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Term
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Definition
Use: NaBH4 in CH3CH2OH to get a primary alcohol
Use: LiAlH4 in (CH3CH2)2 and water work up to get a primary alchol |
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Term
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Definition
Use: NABH4 in CH3Ch2OH
Use: LiAlH4 in (Ch3Ch2)2O and water work up
This process yields a secondary alchol |
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Term
| Oxidation of Primary Alchols |
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Definition
| Use PCC In CH2Cl2 to get an aldehyde |
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Term
| Oxidation of Secondary Alchols |
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Definition
| Use Na2Cr2O7 in H2So4 to get a ketone |
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Term
| Organometallic Reacents- reaciton of metals with haloalkanes |
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Definition
| RX + Li in (CH3Ch2)2O yieldds a RLi which is a alkyllitium reagent |
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Term
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Definition
| RX + Mg yields RMgX in (Ch3Ch2)O R cannot contain acidic groups sh=uch as OH or electrophilic groups such as c=O |
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Term
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Definition
RLi or RMGX + water yields RH
RLi or RMgX + D2O yields RD
Aldehyde or ketone cannot contain other groups tha treact with organometallic reagents such as OH or othe rC=O groups |
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Term
| Reaction of Organometallic Compounds to Aldehydes and Ketones |
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Definition
RLi or RMgX + CH2=O yields primary alchols
RLi or RMgX + Aldehyde yields secondary alcohols
RLi or RMgX + Ketone yields a tertiary alcohol |
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Term
| Alkanes from Haloalkane and Litium Aluminum Hydride |
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Definition
| RX + LiAlH4 yields RH (in Ch3CH2)2o |
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Term
| Alkanes from Haloalkane and Litium Aluminum Hydride |
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Definition
| RX + LiAlH4 yields RH (in Ch3CH2)2o |
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Term
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Definition
ROH + M yields ROM + 1/2 H2
M= Li, Na, K |
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Term
| Using Hydrogen Halides to give you HBaloalkanes from Alchols |
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Definition
Primary ROH uses a concentrated haloalkene (HX, where H is Br or I , in an Sn2 mechanism)
Secondary or Tertiary ROH in concentrated HX ( where X is Cl, BR, or I as a SN1 mechanism) to yield RX |
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Term
| Using phospohorous reagents: |
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Definition
3 ROH + PBr3 yields 3RBr + H3PO3
6ROH + 2 P + 3I2 yields ^ RI 2 H3PO3
Sn2 mechanism with primary and scondary ROH
less likelihood of carbocation rearrangements that with HX |
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Term
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Definition
ROH + SOCL3 in ( N Ch2CH3)2 yields RCl + SO2 + (CheCh2)3 NHCl
ROH + R'So2Cl yields ROSO2R' yields NuDMSO RNu + R'So3- |
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