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232 Organic Chemistry Solutions Manual ABX system, and it sounds like an enol. Compound is chiral so the CH₂ appears as system but the enol is not chiral so the CH₂ is a singlet. Here are the structures with the assignments (in each case the OEt groups provide the 3H triplets and 2H quartets). proton 'X' δ 5.44 exchanges with H 0 H CHO low field proton OEt OEt Et0 H H H H o AB part of ABX δ 2.28 A1 A2 Treatment with acidic ethanol simply makes the diethyl acetal from the aldehyde group Since and A2 are in equilibrium, all A2 is eventually converted into B via Compound again chiral so the ABX system reappears with further coupling of HX to the acetal proton. now four triplets and quartets for the four OEt groups. δ 3.04 H CHO proton 'X' OEt H OEt EtOH CO₂Et A1 B H H C13H2406 AB part of ABX δ 2.52