Carbonyl Chemistry Predict the products This is best

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Reduction Reactions: Sodium Borohydride (Na. BH 4): Carbonyl carbon gets a hydrogen from Na. BH 4, oxygen gets a H from the alcohol solvent Grignard (RMg. X): Carbonyl carbon gets a R group from RMg. X, oxygen gets a H from subsequent acid workup step. Sodium Borohydride (Na. BH 4) with an imine: Imine carbon gets a hydrogen from Na. BH 4, nitrogen gets a H from the alcohol solvent.

Reversible Carbonyl Reactions: Carbonyl + KCN, Ac. OH gives a cyanohydrin: Carbonyl carbon gets a CN from KCN, oxygen gets a H from the acetic acid solvent Carbonyl + catalytic acid + alcohol gives an acetal: Carbonyl carbon gets two OR groups from ROH. If ROH is a diol, then a cyclic acetal is formed. Carbonyl + catalytic acid + primary amine gives an imine: Carbonyl carbon gets a double bond to the amine Nitrogen. The R group on the amine ends up cis to the smallest group on the carbonyl.

Reverse Reactions: Cyanohydrin + base: OH becomes a carbonyl. Cyanide is removed. Acetal + catalytic acid + water: Break C-O bonds to acetal carbon. The two O’s get H’s, the carbon gets a =O Imine + water: Break both C=N bonds. The N gets 2 H’s, the carbon gets a =O

Combination reactions: Aminohydrin formation Carbonyl + KCN + NH 4 Cl: Remove the carbonyl oxygen. Carbonyl carbon gets a CN and an NH 2. This combines imine formation with cyanide attack. Reductive amination Carbonyl + acetic acid + primary amine + Na. BH 3 CN gives an amine: Remove the carbonyl oxygen and one of the amines H’s. Connect the carbon to the nitrogen.

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