Design a synthesis of 2-ethyl-2-hexenoic acid from alcohols of four carbons or fewer.

Enolate Alkylation

The anions from ketones, called enolates, can act as a nucleophile in SN2 type reactions.  Overall an α hydrogen is replaced with an alkyl group and a new carbon-carbon bond is formed.  These alkylations are affected by the same limitations as SN2 reactions previously discussed.  A good leaving group, chloride, bromide, iodide or tosylate, should be used.  Also, secondary and tertiary leaving groups should not be used because of poor reactivity and possible competition with elimination reactions.  Lastly, it is important to use a strong base, such as LDA or sodium amide, for preparing the enolate from the ketone.  Using a weaker base such as hydroxide or an alkoxide leaves the possibility of multiple alkylations occurring, and competing SN2 reactions with the base.

Explanation:

Design is illustrated in the attached document

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