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SolutionsPreparation

1. Which carbonyl compound is obtained?

Give the carbonyl compound obtained in each case:

  1. Oxidation of 2-butanol with K2Cr2O7/H2SO4.
  2. Oxidation of 1-butanol with pyridinium chlorochromate (PCC).
  3. Ozonolysis of 1-methylcyclohexene followed by Zn/H2O.
  4. Hydration of 1-hexyne with H2SO4/HgSO4.
  5. Benzene with propanoyl chloride and AlCl3.
  6. Benzonitrile with ethylmagnesium bromide, followed by acid hydrolysis.
  1. Butanone.
  2. Butanal (PCC does not oxidize the aldehyde to the acid).
  3. 6-Oxoheptanal: the ring is cleaved and a compound with a ketone and an aldehyde is obtained.
  4. 2-Hexanone (Markovnikov addition of water and tautomerism of the enol).
  5. Propiophenone (1-phenyl-1-propanone).
  6. Propiophenone: the intermediate imine is hydrolyzed to the ketone.

2. Two routes to the same ketone

Propose two different methods to prepare cyclohexyl methyl ketone (1-cyclohexylethanone).

  • Oxidation of 1-cyclohexylethanol (for example, with PCC or K2Cr2O7).
  • Hydration of ethynylcyclohexane (H2SO4, HgSO4).
  • Reaction of cyclohexanecarbonyl chloride with lithium dimethylcuprate, (CH3)2CuLi.
  • Reaction of cyclohexanecarbonitrile with CH3MgBr followed by acid hydrolysis.

Any pair of these is valid; in synthesis the one chosen starts from the most accessible materials and does not affect other groups in the molecule.

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