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Organic Chemistry Questions – Mechanisms?
Suggest a sequence of reactions suitable for preparing each of the following compounds from the indicated starting material.
1. 2-propanol from 1-propanol.
2. 3-methyl hex-1-en-3-ol from 1-methylcyclohexene
3. 1,5 diether pentane from cyclopentane
4. 1,2-epoxy-3-bromocyclohexane from cyclohexane
Ugh, and mechanisms too?
1. a) H2SO4 to dehydrate to propene. b) Either H2SO4/CH3CO2H and then hydrolyze the acetate ester with NaOH or Hg(OAc)2/H20 and then NaBH4 to give 2-propanol.
2. Can this be correct? I could suggest a route, but it would be long an ugly as I don’t see any easy way to clip the required bond and generate the alkene. If I am missing something here, show me.
3. I am going to guess at the product here. So first radical bromination to bromocyclopentane, elimination with KOtBu to cyclopentene. Ozone and reductive workup, to dialdehyde, reduce aldehdye to diol with NaBH4. Convert into ether with NaH, and RX to give the ether. Choose R to match the ether the product is supposed to be.
4. Same as 3. to cyclhexene. Allylic bromination with NBS to 3-bromocyclohexene. Treat that with mCPBA to epoxide.
Alkene Reaction Mechanisms – Major/Minor Products (The BASICS part II)
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