Problems and exercisesAlkylation

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1. A synthetic scheme with enamines

Fill the blanks in the following synthetic scheme:

Scheme with blanks: acetone with pyrrolidine (Dean-Stark), 1,3-dibromopropane and H₃O⁺, pyrrolidine again, an intermediate in brackets, H₃O⁺, pyrrolidine and finally benzyl iodide and H₃O⁺

2. Kinetic and thermodynamic enolate

Which main product is obtained when 2-methylcyclohexanone is alkylated with methyl iodide under these conditions: a) LDA at −78 °C and then CH₃I; b) NaOEt in refluxing ethanol and then CH₃I?

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