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The starting material for our experiment, cis-1,2,3,6-tetrahydrophtalic anhydride, can be converted to a cyclic keto diester using the following sequence of reactions. This is an example of a ring contraction procedure. Suggest a plausible mechanism for the last step (formation of the ring). COOMe COOMe 1. MeOH KMnO4 HOOC HOOC 2. SOCI2 COOMe COOMe 1. acetic anhydride 130°C COOMe C) 2. sodium acetate, 1300C COOMe

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CH2 COONa coome coome ㄩ coome Ccome Coome come 130 Ccome Coom

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