Chapter 22: Q53. (page 917)
Question: Identify F in the following reaction sequence. F was converted in several steps to the antidepressant paroxetine (trade name Paxil; see also Problem 9.9).

Short Answer
Answer
Compound F is:

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Chapter 22: Q53. (page 917)
Question: Identify F in the following reaction sequence. F was converted in several steps to the antidepressant paroxetine (trade name Paxil; see also Problem 9.9).

Answer
Compound F is:

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Question: Draw the three possible resonance structures for an acid bromide, . Then, using the pKa values in Appendix A, decide if RCOBr is more or less stabilized by resonance than a carboxylic acid (RCOOH).
Question: Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.

Draw the products formed (including stereoisomers) when each compound is reduced with NaBH4in CH3OH.
What organocuprate reagent is needed to convert CH3CH2COCIto each ketone?
a.

b.

c.

Question: Fenofibric is a cholesterol-lowering medication that is converted to fenofibric acid, the active drug, by hydrolysis during metabolism. What is the structure of fenofibric acid?

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