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Chapter 25: 57 (page 1044)

Identify A, B, and C, three intermediates in the synthesis of the pain reliever and anesthetic fentanyl.

Short Answer

Expert verified

It is used for the treatment of patients having severe pain and it relieves the pain after the surgery.

Step by step solution

01

Fentanyl

It is used for the treatment of patients having severe pain and it relieves the pain after the surgery.

02

Formation of products

The reaction of (2-bromoethyl)benzene with piperidin-4-one forms A as shown below:

Formation of A

The reaction of A with pyridine in the presence of mild acid forms B as shown below:

Formation of B

The reaction of B with forms C as shown below:

Formation of C

The reaction of C with propionyl chloride in the presence of pyridine forms fentanyl as shown below:

Formation of fentanyl

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Most popular questions from this chapter

Question:The pKa of the conjugate acid of guanidine is 13.6, making it one of the strongest neutral organic bases. Offer an explanation.

Treatment of compound D with LiAlH4 followed by H2O forms compound E. D shows a molecular ion in its mass spectrum at m/z= 71 and IR absorptions at 3600-3200cm-1 and . E shows a molecular ion in its mass spectrum at m/z= 75 and IR absorptions at 3636cm-1 and 3600-3200cm-1 . Propose structures for D and E from these data and the given 1H NMR spectra.

Question: Draw the structure that corresponds to each name.

  1. N-isobutylcyclopentanamine
  2. tri-tert-butylamine
  3. N, N-diisopropylaniline
  4. N-methyl pyrrole
  5. N-methylcyclopentanamine
  6. 3-methylhexan-2-amine
  7. 2-sec-butylpiperidine
  8. (S)-heptan-2-amine

Rank the nitrogen atoms in each compound in order of increasing basicity. Isoniazid is a drug used to treat tuberculosis, whereas histamine causes the runny nose and watery eyes associated with allergies.

Draw a stepwise mechanism for the following reaction.
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