Extras for Exam I
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Extras for Exam I
- take __ (works best with __)
- treat with __
- R can be __
alkyl, vinyl, aryl
second alcohols turn into. Tertiary alcohols are __. You would have to do what?
inert to oxidation technically
you'd have to break the CC bond
Ways to oxidize that we are using?
Condensation reactions will form the __.
if there are no H on the carbon, you won't __ it to a __.
The __ is very difficult to make. They are very easily __.
PCC Oxidizes primary acohols to __.
Secondary alcohols to __
pcc IS __
What are some qualitative tests?
chromium tests: primary and secondary go from orange to green, while tertiary don't react
- Primary --> __ and Secondary --> __
- same as __.
- higher yielding to __.
- no __.
__ shouldn't be used on primary because you get both __ and __.
H2 and Raney Nickel
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)
__ is a good solvent because it is basic.
Stereochemistry does what with Tosylates?
remains because the reaction is between O and Cl, not O and C
__ is 98%. It either goes or it doesn't.
- which does it?
- which carbocations won't rearrange?
- which will?
- what happens with primary?
tertiary and secondary
react slowly; not the way to go
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
alkene qualitatitve test
reddish brown --(Br2)--> colorless
To convert primary and secondary to alkyl halides, what do we use?
- All are __
Which shift if faster?
Types of esters
Sulfuric and phosphoric acids are __ in the reaction. The __ of the acid is removed. The __ of the ROH stays.
Protection of alcohols: use what?
What kind of reaction?
Run in presence of what?
It then becomes what?
Sn2 (split out HCl)
no longer an alcohol but a silyl ether
What is the reverse reaction for protecting groups?
dilute the acid; deprotonate