Exam 2

Question 1

Oxidative cleavage
of diol

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-CHO --> -COOH

Answer 1

Sodium periodate (NaIO4)
NaOH, EtOH, 25oC

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Lindgren-Pinnick Oxidation
NaClO2/ NaH2PO4,…

Question 2

-OH (I) -> COOH

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Ketone -> a-OH ketone

Answer 2

PDC (Pyridinium dichromate)
Corey-Schmidt Ox.
(PyH)2Cr2O7
DMF
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David Oxaziridine
1) KHMDS, THF, -78 oC
2) David oxaziridine

Question 3

Diol to lactone

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Selenation/oxidation/elimination

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-OH (II)

Answer 3

Fetizon’s reagent
Ag2CO3, Celite, reflux in C6H6

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1) LDA, THF -78 oC
2)PhSeBr
3) H2O2
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Steven Oxidation
NaClO, AcOH

Question 4

Weinreb amide to 
aldehyde
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Acyl chloride to 
aldehyde

Answer 4

DIBAL, DCM, -78oC

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H2 Pd/BaSO4
or STBA, diglyme, THF…

Question 5

Acid to alkane

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1,2-Diol to olefin

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Halide to alkane

Answer 5

Barton decarboxylation
--> Barton ester
then Bu3SnH, AIBN, THF, reflux
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Eastwood Deoxygenation
1) HC(OEt)3, AcOH
2) 200 oC

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Radical dehalogenation
Bu3SnH, AIBN, THF, 80 oC