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Solutions to Problems . 465 52. Two aldoheptoses are formed. After one gives an optically active the other an inactive meso compound. CHO COOH HO H HO H HO H HO H HNO3 HO H HO H HO H HO H H OH H OH CH₂OH COOH Active CHO COOH H OH H OH H HO H HNO3 HO H HO H HO H H H OH H OH CH₂OH COOH Meso HOCH₂ HO CH₂ H 0 53. (a) HO CH₂OH CH₂OH OH OH OH CH₂OH 0 HO HO OH CH₂OH OH OH Product after protonation (both anomers) OH (b) (Three equatorial and OH two axial substituents) HO HO (c) 0.65 kcal mol (Table 2-1)