Chapter 22: Q4P (page 734)
Write the complete mechanism for the deuteration of acetone on treatment with D3O+.
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Chapter 22: Q4P (page 734)
Write the complete mechanism for the deuteration of acetone on treatment with D3O+.
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How would you synthesize the following compounds from cyclohexanone?
More than one step may be required.

How many acidic Hydrogens does each of the molecules listed in Problem 22-1 have? Identify them.
Show how you might prepare 1-penten-3-one from 3-pentanone.
If methanol rather than water is added at the end of a Hell–Volhard–Zelinskii reaction, an ester rather than an acid is produced. Show how you would carry out the following transformation, and propose a mechanism for the ester forming step.
The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold Helminthosporium sativum, involves the following base treatment of a keto tosylate.
What kind of reaction is occurring? How would you complete the synthesis?

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