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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

Expert verified

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: Consider the following SN2 reaction.

  1. Draw a mechanism using curved arrows.
  2. Draw an energy diagram. Label the axes, the reactants, products, Ea , and ∆H°. Assume that the reaction is exothermic.
  3. Draw the structure of the transition state.
  4. What is the rate equation?
  5. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from Br-to I-;[2] The solvent is changed from acetone to CH3CH2OH ; [3] The alkyl halide is changed from CH3(CH2)4Br to CH3CH2CH2CH(Br)CH3 ; [4] The concentration of CN- is increased by a factor of five; and [5] The concentrations of both the alkyl halide and CN-are increased by a factor of five.

Question: Identify the stronger nucleophile in each pair

a.NH3 NH2 NH3,NH2

b.CH3 NH2 ,CH3 OH CH3NH2,CH3OH

c.CH3CO2- ,CH3CH2O- CH3CO2-,CH3CH2O-

Question: Which molecules contain good leaving groups?

a.

b.

c.

d.

CH3-CH3

Question: Draw the products formed when each alkyl halide is treated with NaCN.

a.

b.

Question: Rank the following carbocations in order of increasing stability.
See all solutions

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