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DesLee26
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Gilman Reagent
- take __ (works best with __)
- treat with __
- R can be __
- alkyl halides
- R-Br
- lithium metal
- alkyl, vinyl, aryl
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second alcohols turn into. Tertiary alcohols are __. You would have to do what?
- ketones
- inert to oxidation technically
- you'd have to break the CC bond
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Ways to oxidize that we are using?
NaCr2O7/H2SO4
NaOCl
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Condensation reactions will form the __.
if there are no H on the carbon, you won't __ it to a __.
ester
oxidize
carbonyl
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The __ is very difficult to make. They are very easily __.
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PCC Oxidizes primary acohols to __.
Secondary alcohols to __
aldehydes
ketones
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What are some qualitative tests?
chromium tests: primary and secondary go from orange to green, while tertiary don't react
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DMSO (__)
- Primary --> __ and Secondary --> __
- same as __.
- higher yielding to __.
- no __.
- Swern oxidation
- aldehydes
- ketones
- PCC
- PCC
- heavy metals
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__ shouldn't be used on primary because you get both __ and __.
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Reduction: __
- LiAlH4
- NaBH4
- H2 and Raney Nickel
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Conversion of Alcohol into a LG
- 1) Tosylate (a leaving group if its CA is stable and strong
- -- R-OTs= good LG
- -- You can reduce an alcohol to an alkane with LiAlH4. H- will remove the OTs
2) Alkyl Halides (HX)
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__ is a good solvent because it is basic.
Stereochemistry does what with Tosylates?
pyridine
remains because the reaction is between O and Cl, not O and C
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For reduction,
__ is 98%. It either goes or it doesn't.
catalytic hydrogenation
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Sn1 reactions
- which does it?
- which carbocations won't rearrange?
- which will?
- what happens with primary?
- tertiary and secondary
- tertiary
- secondary
- react slowly; not the way to go
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What does the Lucas Test distinguish between?
- tertiary, secondary, primary
- tertiary reacts in less than one minute
- secondary reacts in one to five
- primary reacts in several minutes to sevearl days
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alkene qualitatitve test
reddish brown --(Br2)--> colorless
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To convert primary and secondary to alkyl halides, what do we use?
- All are __
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Which shift if faster?
methyl
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Types of esters
- Fischer
- Tosylate
- sulfate
- nitrate
- phosphate
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Sulfuric and phosphoric acids are __ in the reaction. The __ of the acid is removed. The __ of the ROH stays.
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Protection of alcohols: use what?
What kind of reaction?
Run in presence of what?
It then becomes what?
chlorotrimethylsilane
Sn2 (split out HCl)
pyridine
no longer an alcohol but a silyl ether
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What is the reverse reaction for protecting groups?
dilute the acid; deprotonate
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