Carbonyl Reaction ProductsOnline version Products from Reactions with Carbonyls "K/A:" ketone or aldehyde "P:" primary "S:" secondary by Kevin Shea CHM 222 1 Primary Alcohol 2 Secondary Alcohol 3 Tertiary Alcohol 4 Ketone 5 Carboxylic Acid 6 Amine Acid Chloride + NaBH4 or LAH Ester + LAH Aldehyde + NaBH4 or LAH Formaldehyde + RMgX or RLi Epoxide + RMgX or RLi Ketone + NaBH4 or LAH Aldehyde + RLi or RMgX Epoxide-R + RLi or RMgX Epoxide-R + NaBH4 or LAH Ketone + RLi or RMgX Acid Chloride + RLi or RMgX Ester + RLi or RMgX Ester-2R + RLi or RMgX Epoxide + LAH or NaBH4 Carboxylate + RLi Conj. Carbonyl + R2CuLi Secondary OH + PCC/H2CrO4 R-CN + RLi or RMgX CO2 + RLi or RMgX Primary Alcohol + H2CrO4 RCN + H3O+, H2O Amide + LAH K/A + ammonia, NaBH3CN K/A + p. amine, NaBH3CN K/A + s. amine, NaBH3CN RCN + LAH