Cycloalkanecarboxylic acids, synthesis

The procedure described is essentially that of Shioiri and Yamada. Diphenyl phosphorazidate is a useful and versatile reagent in organic synthesis. It has been used for racemlzatlon-free peptide syntheses, thiol ester synthesis, a modified Curtius reaction, an esterification of a-substituted carboxylic acld, formation of diketoplperazines, alkyl azide synthesis, phosphorylation of alcohols and amines,and polymerization of amino acids and peptides. - Furthermore, diphenyl phosphorazidate acts as a nitrene source and as a 1,3-dipole.An example in the ring contraction of cyclic ketones to form cycloalkanecarboxylic acids is presented in the next procedure, this volume. 

Synthesis of cycloalkanecarboxylic acids from a,co-dihaloalkanes and diethyl sodiummalonate (see 1 st edition)... 

The malonic acid synthesis can be used to prepare cycloalkanecarboxylic acids by a double alkylation using a dihalide. Write the structure of the product of each of the steps in the following sequence. 

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