Question

1) (27 points) Provide the missing reactants, reagents or products 1) NaBH4 2) H30+ H30* H-= - Nat CO2H

HON H+ muly & West NH NH2, KOH 1) PP / H 2) H30+

Croz H2SO4 HO H20 1) Mg, EtOEt OH 3) H30+

Determine the missing products or reagents. Draw arrow pushing mechanisms for 3 of the above reactions.

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Answer #1

2.so med host HO сор 11 BOSH mad on neto 90 any Dewane atl Ou

1. NaBH4 reduce the ketoen to alcohol

2. Hydrolysis of acetal gives ketome and diol

3. Imine formation by nucleophilic addition

4. Wolff-Kishnner reduction convert ketone to Alkane

5. Wittig reaction gives alkene from carbonyl compounds and phosphorus ylide then hydroysis of acetal givrs back the aldehydes.

6. CrO3 is a strong oxidizing agent which oxidize the 2° alcohol to ketone and primary alcohol to carboxylic acid.

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