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SolutionsReactivity

1. Products

Give the main organic product of ethyl benzoate with: a) aqueous NaOH, then H3O+; b) NH3; c) LiAlH4, then H2O; d) two equivalents of CH3MgBr, then H2O.

  1. Benzoic acid (and ethanol).
  2. Benzamide.
  3. Benzyl alcohol (and ethanol).
  4. 2-Phenyl-2-propanol, C6H5C(OH)(CH3)2.

2. Claisen condensation

Which product does ethyl acetate give with sodium ethoxide, followed by dilute acid?

Ethyl acetoacetate (ethyl 3-oxobutanoate), CH3COCH2COOEt, a β-dicarbonyl compound.

The enolate of one molecule attacks the carbonyl of another; ethoxide is lost (addition-elimination).

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