Chapter 17: 7 P (page 539)
Question: What reagent would you use to accomplish each of the following reactions?
(a)

(b)

(c)

Short Answer
(a)

(b)

(c)

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Chapter 17: 7 P (page 539)
Question: What reagent would you use to accomplish each of the following reactions?
(a)

(b)

(c)

(a)

(b)

(c)

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How would you prepare the following substances from cyclopentanol?
More than one step may be required.
(a) Cyclopentanone
(b) Cyclopentene
(c) 1-Methylcyclopentanol
(d) trans-2-Methylcyclopentanol
Question: Predict the products of the following reactions:
(a)

(b)

(c)

TMS ethers can be removed by treatment with fluoride ion as well as by acid-catalyzed hydrolysis. Propose a mechanism for the reaction of cyclohexyl TMS ether with LiF. Fluorotrimethylsilane is a product.
How would you carry out the following transformation, a step used in the commercial synthesis of (S)-ibuprofen?

What products would you obtain from reaction of 1-pentanol with the
following reagents?
(a)
(b)
(c) , ,
(d) Dess–Martin periodinane
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