Reaction with Cuprammonium and Other Reactions of Carbohydrates

Correlations between Reaction with Cuprammonium and Other Reactions of Carbohydrates 

Since reaction with cuprammonium provides a measure of the relative position of adjacent hydroxyl groups it is of interest to compare cuprammonium data with existing information on other reactions in which two hydroxyl groups participate. 

One instance where correlation with cuprammonium data appears possible is the reaction between adjacent cis glycol groups and acetone to form isopropylidene derivatives. Although data on the kinetics and equilibria of isopropylidene formation are too meager to prove that reactivity with acetone parallels reactivity with cuprammonium, isolated observations support such a supposition. Knauf, Hann, and Hudson12 have noted the ease of formation of the acetone derivatives of D-mannosan, and this is one of the substances most reactive toward cuprammonium.6 Tipson13 has noted that the optically active 2,3-butanediols react with acetone more readily than the meso form, and this is the order in which these substances react with cuprammonium.14 

Comparison of Shifts in Optical Rotation Due to Reaction with Acetone and with Cuprammonium 

Substance [ Id Solvent Reference Shift in Molecular Rotation Refer- ence 

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