Answer to Question #95303 in Organic Chemistry for Natasha Prasad

Question

The reaction scheme shows the synthesis of 2-methylpentnoic acid from diethyl malonate (malonic ester).


i) The reagents in step 1 are: (i) EtO- (ii) an alkyl halide. What alkyl halide is required in step 1? Draw a mechanism for the reactions that occur in step 1.
ii) Suggest reagents for step 2.
iii) Suggest reagents for step 3. Name this type of reaction.
iv) Step 4 is a thermal decarboxylation reaction. Show a mechanism for the decarboxylation in step 4 that results in the formation of 2-methylpentanoic acid, and explain why the decarboxylation of the dicarboxylic acid in step 4 is particularly facile that is it readily occurs. [4 marks]

Answer 1

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