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Chapter 7: PROBLEM7.64 (page 293)

Question: Fluticasone, the chapter-opening molecule, can be prepared by the following reaction. Draw a stepwise mechanism for this reaction.

Short Answer

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ANSWER

Formation of the fluticasone by theSN1 mechanism

Step by step solution

01

Preparation of fluticasone

Fluticasone is used for the treatment of cold-like nasal symptoms.

It is prepared by the reaction of compound A with BrCH2F and K2CO3by using DMF as a solvent. The reaction proceeds by the SN2 mechanism.

The role of the potassium carbonate is to abstract a proton from the thioacetic acid group. The alkyl halide then attacks the thioacetate, and the bromo group acts as a leaving group.

02

 Stepwise mechanism for the preparation of fluticasone

The first step involves the attack of potassium carbonate on the thioacetate group. This results in the loss of the proton and causes the attack of the alkyl halide BrCH2F . The bromide group acts as leaving group.

Formation of the fluticasone by theSN1 mechanism

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Most popular questions from this chapter

Question: Explain why quinuclidine is a much more reactive nucleophile than triethylamine, even though both compounds have N atoms surrounded by three R groups.

Question: Consider the following SN1 reaction.

  1. Draw a mechanism for this reaction using curved arrows.
  2. Draw an energy diagram. Label the axes, starting material, product Eaand 鈭�H掳. Assume that the starting material and product are equal in energy.
  3. Draw the structure of any transition states.
  4. What is the rate equation for this reaction?
  5. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from I- to Cl-;[2] The solvent is changed from H2O to DMF; [3] The alkyl halide is changed from (CH3)2 C(I) CH2CH3 to (CH3) CHCH(I)CH3 ; [4] The concentration of H2O is increased by a factor of five; and [5] The concentrations of both the alkyl halide and H2O are increased by factor of five.

Question: Uridine monophosphate (UMP) is one of the four nucleotides that compose RNA, the nucleic acid that translates the genetic information of DNA into proteins needed by cells for proper function and development. A key step in the synthesis of UMP is the reaction of A with B to form C, which is then converted to UMP in one step. Draw a stepwise mechanism for this SN1 reaction.

Question: Device a synthesis of each compound from an alkyl halide using any other organic or inorganic reagents.

a.

b.

c.

d.

Question: When (R)-6-bromo-2,6-dimethylnonane is dissolved in , nucleophilic substitution yields an optically inactive solution. When the isomeric halide (R)-2-bromo-2,5- dimethylnonane is dissolved in under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.
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