2. Complete part of the following assigned problem from the textbook by drawing intermediates A, B, and C. [4 pts each] • Do not abbreviate any part of the structures. Use the work space for your rough drafts, and put your final answers in the indicated spaces. 23.58 Identify A, B, and C, three intermediates in the synthesis of the pain reliever and anesthetic fentanyl. H-N A + -Br -NH2 NaBH3CN A B N -N mild acid pyridine fentanyl B C Space to work. Nothing in the space below the heavier line will be graded.

2. Complete part of the following assigned problem from the textbook by drawing intermediates A, B, and C. [4 pts each] • Do not abbreviate any part of the structures. Use the work space for your rough drafts, and put your final answers in the indicated spaces. 23.58 Identify A, B, and C, three intermediates in the synthesis of the pain reliever and anesthetic fentanyl. H-N A + -Br -NH2 NaBH3CN A B N -N mild acid pyridine fentanyl B C Space to work. Nothing in the space below the heavier line will be graded.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.30P: Nicotinic acid, more commonly named niacin, is one of the B vitamins. Show how nicotinic acid can be...

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2. Complete part of the following assigned problem from the textbook by drawing intermediates A, B, D, and E. [4 pts each] • Do not abbreviate any part of the structures. Use the work space for your rough drafts, and put your final answers in the indicated spaces. B, D, and E 20.43 Identify compounds A-M in the following reaction sequence. A Br NaCN H3O+ SOCI₂ A B D [1] (CH3)2CuLi [2] H₂O E D B E
Complete the following reactions by giving appropriate reagents: Zn(Hg) (1)? AICI HCI HNO₂ CI H₂SO4 (3)? (4)? NO₂ (2)?
Galantamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of Alzheimer's disease. In a synthesis of galantamine and related compounds (J. Org. Chem. 2015, 80, 1952-1956), compound 1 was converted into compound 2. Propose an efficient synthesis for the conversion of 1 to 2 A. NaOH MeO D. DMP or PCC G. HBr MeO B. H₂SO4, H₂O, HgSO4 E. Na2Cr₂O7, H₂SO4, H₂O H. 1) O3; 2) DMS H 2 The conversion of 1 to 2 can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. C. 1) BH3-THF; 2) H₂O2, NaOH F.HBr, ROOR I. TsCl, py Meo I₁, N Me Galanthamine OH
Galantamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of Alzheimer's disease. In a synthesis of galantamine and related compounds (J. Org. Chem. 2015, 80, 1952-1956), compound 1 was converted into compound 2. Propose an efficient synthesis for the conversion of 1 to 2 A. NaOH MeO D. DMP or PCC G. HBr 1 MeO B. H₂SO4, H₂O, HgSO4 E. Na₂Cr₂O7, H₂SO4, H₂O H. 1) O3; 2) DMS H 2 x I. TsCl, py The conversion of 1 to 2 can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. C. 1) BH3-THF; 2) H₂O2, NaOH F.HBr, ROOR = MeO Ill. N Me Galanthamine OH
Draw the major organic product of each of the following reactions.
1) Show how m-toluidine (shown on the right) can be converterd to the following compounds using any neccesary reagents. (You can use a previously synthesized compound to carry on). a) H₂C- b) d) c) H₂C m-toluonitrile m-iodotoluene H₂C. CN m-cresol CHÍNH, OH H₂C.
What reagents would you use to carry out the following reaction? (A) H₂ / Pt (B) (C) (D) H₂/Lindlar's ??? Li, EtNH₂ followed by NH4Cl H₂O₂ / NaOH
2. The following drugs are synthesised using the methods in this chapter and previous chapters. Derive a synthesis for each, starting with any compounds containing no more than six carbons atoms. A. Phenacetin, used with aspirin and caffeine in pain-relief medications B. Methamphetamine, once considered a safe diet pill, but now known to be addictive and destructive to brain tissue. C. Dopamine, one of the neurotransmitters in the brain. Parkinson's disease is thought to result from a dopamine deficiency.
Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen.
Hw.51.
Hh.115.
49. Identify structures A and B in the following reaction sequence. 1).0₂ 2) DMS NaOH H₂O B C₁0H₁0 50. Provide a stepwise mechanism for the reaction A-----> B in question 49.