I am having trouble with figuring out the overall transformations for this synthesis problem..?
Just really part a) I think I got part b) already.
Would it be a simple 1.)HgO(Ac)2 2.)NaBH4 and then add them together???
Let me know what you think.
Answer:
Convert cyclopentene to the alcohol (hydroboration/oxidation perhaps), and then Jones it up to cyclopentanone. Brominate the propene at the allylic position to give allyl bromide. Deprotonate the cyclopentanone alpha to the carbonyl and use the enolate as a nucleophile to react with the allyl bromide. Then reduce the ketone with borohydride.
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Part a can be synthesized by first epoxidizing the cyclopentene with H2O2. Next propene can be brominated in the allylic position with NBS (N-bromosuccinimide). This is then converted to allyl magnesium bromide by reacting it with Mg. The resulting Grignard reagent is then reacted with the epoxide. The product of this will be your desired product.
Part B can be synthesized by forming the anion of acetylene and reacting it with ethyl bromide. That product is then reacted in the same way again with ethyl bromide (a more modern way of doing this transformation is by the Sonogashira reaction. You can find it on Wikipedia). The resulting product, 3-hexyne, can then be reduced to the double bond by hydrogenating using Lindlar catalyst (Pd-CaCO3 poisoned with lead acetate). This gives trans 3-hexene. The cyclopropane is then formed by reacting CH2I2 with Zn(Cu). This reaction is known as the Simmons-Smith reaction. You can find more information on it on Wikipedia. The product of this reaction is your desired product. Hope this helps you out. Good luck.
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