The compound 3,5,5-trimethyl-2-cyclohexenone can be synthesized using acetone and ethyl acetoacetate as sources of carbon atoms. New carbon-carbon bonds in this synthesis are formed by a combination of aldol reactions and Michael reactions. Show reagents and conditions by which this synthesis might be accomplished. lel COOEt exelte. ČOOH 3,5,5-Trimethyl- 2-cyclohexenone

4. Draw the organic products of the reactions of (R)-2-iodobutane with azide ion and methanol. Draw allstereoisomers expected to form. (R)-2-iodobutane Na*N3* CH3OH

Draw the structure(s) of the major organic product(s) of the following reaction. aqueous H₂SO + KCN

1. NaOEt CO₂Et 2. H3O+ 3. heat Br H3C CO₂H CO2 H3C CO₂Et The malonic ester synthesis is a carbonyl alkylation reaction. It is used to prepare carboxylic acids from primary alkyl halides, lengthening the carbon chain by two atoms. Thus, the product can be visualized as being a "substituted acetic acid." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 22 CX EtO₂C EtO₂C HOCH2CH3 HOCH2CH3 EtO₂C EtO₂C