Enamines can serve as enolate surrogates in reactions at the a-carbon. In the reaction sequence, the structures of the enamine addition product - the initial zwitterion and its neutral tautomer - are shown. Draw the structures of the two reactants forming these intermediates, and draw the structure of the final product, obtained via hydrolysis of the neutral intermediate. initial zwitterionic intermediate Reactants 'N'+ tautomerization hydrolysis product neutral intermediate + H₂O

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

Rank the reactivity of the compounds below toward nucleophilic acyl substitution by writing the compounds' letters in the proper blanks in the box below. `NH CI Br CH3 CH3 A В C E rank compounds for acyl substitution reactivity most least reactive reactive

Which carbon will attack the alkyl halide (methyl iodide) in the major organic product of the following substitution reaction? A A B с D B H₂ с CH3 D 1) LDA, THF 2) CH₂I

Show how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.