UBC CHEM 233 REAGENTS QUESTIONS AND CORRECT
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NaBH4 Ans✓✓✓Reducing Agent: aldehydes to 1* alc, ketones to 2* alc
LiAlH4 (LAH) Ans✓✓✓Reducing agent: aldehydes to 1* alc, Ketones
to 2* alc, Carboxylic acid to 1* alc, Esters to two 1* alc
PCC (CrO3/Pyridine/HCl) Ans✓✓✓Oxidizing agent: 1* alc to
aldehyde, 2* alc to ketone cannot oxidize further
Jones Reagent (CrO3/H2SO4/H2O) Ans✓✓✓Oxidizing agent: 1*alc to
carboxylic acid, 2* alc to ketone, aldehyde to carboxylic acid
H2/Pd or H2/Pt or H2/Ni Ans✓✓✓Strong Protonator: Alkyne to alkane,
alkene to alkane
Lindlars Cat./ H2 or Li/NH3 Ans✓✓✓Protonator: alkyne to cis alkene
(same side)
NaNH3 Ans✓✓✓Protonator: alkyne to trans alkene (opposite sides)
NADH Ans✓✓✓Natural reducing agent: similar to NaBH4
DETAILED ANSWERS (VERIFIED ANSWERS) |ALREADY
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NaBH4 Ans✓✓✓Reducing Agent: aldehydes to 1* alc, ketones to 2* alc
LiAlH4 (LAH) Ans✓✓✓Reducing agent: aldehydes to 1* alc, Ketones
to 2* alc, Carboxylic acid to 1* alc, Esters to two 1* alc
PCC (CrO3/Pyridine/HCl) Ans✓✓✓Oxidizing agent: 1* alc to
aldehyde, 2* alc to ketone cannot oxidize further
Jones Reagent (CrO3/H2SO4/H2O) Ans✓✓✓Oxidizing agent: 1*alc to
carboxylic acid, 2* alc to ketone, aldehyde to carboxylic acid
H2/Pd or H2/Pt or H2/Ni Ans✓✓✓Strong Protonator: Alkyne to alkane,
alkene to alkane
Lindlars Cat./ H2 or Li/NH3 Ans✓✓✓Protonator: alkyne to cis alkene
(same side)
NaNH3 Ans✓✓✓Protonator: alkyne to trans alkene (opposite sides)
NADH Ans✓✓✓Natural reducing agent: similar to NaBH4