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How do you make an Ether?
- A. 1)Hg(OAc)2,R-OH 2)NaBH4
- B. Williamson Ether Synthesis
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What must the starting material be for Williamson Ether Synthesis?
A primary (best) or secondary alcohol
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What kind of alkyl halide is required in a Williamson Ether Synthesis?
A 1° alkyl halide
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What are the rules of Ether rxns?
- A. If the starting ether has only 1° or 2° carbons the halide will do SN2 to the less substituted carbon
- B. If the starting ether has 3° carbon the halide will do SN1 to the most substituted carbon
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How does the Oxymercuration make the ether?
It adds the R-OH to the most substituted carbon and then the NaBH4 takes the H off the alcohol to make the ether.
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What does PBr3 do?
It kicks off an alcohol
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What adds 2 OH groups to an alkene?
OsO4 and NaHSO3
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What does NaBH4 do?
It reacts with carbonyls except for Carboxylic acids and Esters, to make an alcohol
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What does PCC do to a primary alcohol?
It turns it into an aldehyde
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What does ozonolysis (O3, DMS) do?
Make 2 carbonyl groups on both sides of an alkene after breaking it.
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How do you make a ketone from a 2° alcohol?
- A. CrO3, heat and acetone (aq)
- B. Na2Cr2O7, H2SO4 and H2O
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How do you turn a carbonyl into an alcohol?
- A. 1)LiAlH4 2)H2O
- B. NaBH4, MeOH or H2O
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What does Ph3PR do?
It replaces the carbonyl with an alkene and the R group
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What does CrO3 H2SO4 do to a 1° alcohol
Turns it into a carboxylic acid
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What does POCl3 do?
Turns a 2° alcohol to an alkene to the least sub carbon
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How do you turn a carbonyl into an acetal? How do you turn it back?
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Mechanism for forming acetal
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How do you get rid of a carbonyl?
- 1) H+, H2NNH2
- 2) KOH, H2O (100-200°C)
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How do you turn an alkyne to an aldehyde?
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How do you turn an alkyne into a ketone?
HgSO4, H2SO4
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How do you turn an ester into a carboxylic acid?
H+, H2O
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