Chapter 17: Q63P (page 848)
Show how the following compounds can be prepared from cyclohexanone:

Short Answer
The answer is,

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Chapter 17: Q63P (page 848)
Show how the following compounds can be prepared from cyclohexanone:

The answer is,

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The 1 H NMR chemical shifts of nitromethane, dinitromethane, and trinitromethane are at d 6.10, d 4.33, and d 7.52. Match each chemical shift with the compound. Explain how chemical shift correlates with pKa.
If the preference for formation of a six-membered ring were not so great, what other cyclic product would be formed from the intramolecular aldol addition of
a.2,6-heptanedione? b. 2,8-nonanedione?
What compound is formed when a dilute solution of cyclohexanone is shaken with NaOD in for several hours?
Orsellinic acid, a common constituent of lichens, is synthesized from the condensation of acetyl thioester and malonyl thioester. If a lichen is grown on amedium containing acetate that was radioactively labeled with 14C at the carbonyl carbon, which carbons will be labelled in orsellinic acid?

Do a retrosynthetic analysis on each of the following compounds, ending with available starting materials.
(a)

(b)

(C)

(D)

(e)

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