Reactants + Reagents = Products

Aldehyde or Ketone, NaBH4

Secondary alcohol, keep structure and swap out carbonyl for OH is formed when an aldehyde or ketone reacts with sodium borohydride (NaBH4), resulting in the reduction of the carbonyl group to a hydroxyl group. This reaction typically transforms the aldehyde or ketone into a secondary alcohol, showcasing the effectiveness of NaBH4 as a reducing agent.

Aldehyde or Ketone, LiAlH4

Primary alcohol, resulting from the reduction of the carbonyl group to a hydroxyl group when an aldehyde or ketone reacts with lithium aluminium hydride (LiAlH4), demonstrating the strong reducing ability of LiAlH4.

Aldehyde or Ketone, R-MgBr

Secondary or Tertiary alcohol, formed when an aldehyde or ketone reacts with a Grignard reagent (R-MgBr), which adds an alkyl group and reduces the carbonyl group to a hydroxyl group, highlighting the nucleophilic nature of Grignard reagents.

Aldehyde or Ketone, HCN

Definition: Cyanohydrin, produced when an aldehyde or ketone reacts with hydrogen cyanide (HCN), resulting in the addition of a cyano group and the formation of a hydroxyl group, demonstrating the nucleophilic addition mechanism. This reaction leads to the formation of a cyanohydrin, where a cyano group is introduced at the carbon atom of the carbonyl and a hydroxyl group is also present. Both HO and CN attached to the carbon.

Acid Chloride or Anhydride, Amines or Alcohols

Amide or Ester formed

Ester, excess grignard

Tertiary alcohol, identical R groups on bottom and right, OH on top

Ester, NaOH

carboxylic acid and alcohol, ring to chain if needed and alcohol on left of chain and carboxylic acid on right of chain

Ester, H20 then H30+

Carboxylic acid and alcohol

Carboxylic acid, excess LiAlH4 then H30+

Alcohol, same setup but swap carboxylic acid with alcohol

Amide, LiAlH4 then H20

Amine, swap C=0 with two H

Nitrile, LiAlH4 then H2O

Amine CH2NH2