Question

If the Favorskii R of 2-chlorocyclohexanone is carried out using sodium ethoxide in ethanol, the product is ethyl cyclopentanecarboxylate, shown below. CI CH,CH2O Na The reaction procceds via a 5-step mechanism and can be formulated as follows. Step 1: Formation of an enolate ion 1 and ethanol. Step 2: An intramolecular alkylation reaction, with enolate ion I as the nucleophile, to yield a fused ring intermediate 2 and Cr. Step 3: Formation of a tetrahedral carbonyl addition intermediate 3 Step 4: Collapse of the intermediate and breaking of one of the ring bonds to give intermediate 4. Step 5: Proton transfer to yield the final cyclopentanecarboxylate product Plan out the full mechanism on a sheet of paper, then draw intermediate 2 below You do not have to consider stereochemistry. . You do not have to explicitly draw H atoms Do not include lone pairs in your answer. They will not be considered in the grading. Do not include counter-ions, eg., Na", I, in your answer Use the "flat" representation of rings in your drawing. Previous

Answer 1

CH3CHO NG Cyclahexanone lote Solution ethox de in ethonol to gv ehy cy clopentonecesboay e in ethano -lote Mechan: s m: CH220 c1 CH2O Cl

hydra gen comes frem the ethanol [CH3cHyO-H] 6 2 4

Intermediate 2