19.42 Although codeine occurs in low concentration in the opium poppy, mostof the codeine used in medicine is prepared from morphine (the principalcomponent of opium) by the following reaction. Explain why selectivemethylation occurs at only one OH in morphine to give codeine. Codeineis a less potent and less addictive analgesic than morphine.HOHOmorphineN[1] KOH[2] CH₂IwwwwwwHOcodeineN

Approach to solving the question: As we know, KOH is a strong base and abstract the most acidic…

Answered: 19.42 Although codeine occurs in low…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter23: Carbonyl Condensation Reactions

Section23.SE: Something Extra

Problem 45MP

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17.36 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. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N Tamoxifen
16.51 Propose a plausible mechanism for the following transformation: Heat
Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal anti-inflammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.
Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal anti-inammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.
Draw a stepwise mechanism for the formation of A from an alcohol and acid chloride. A was converted in one step to blattellaquinone, the sex pheromone of the female German cockroach, Blattella germanica.
Draw a structural formula for the product formed by treating butanal with each reagent. (a) LiA1H4LiA1H4 followed by H2OH2O (b) NaBH4NaBH4 in CH3OH/H2O (c) H2/Pt (d) Ag(NH3)2+in NH3/H2O (e) H2CrO4, heat (f) HOCH2CH2OH,HCl
Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal antiinflammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.
Enalapril, a drug used to treat hypertension, is prepared from compounds D and E by reductive amination. What is the structure of enalapril?
18.26 Predict the products of the following ether cleavage reactions: LOCH CH3 OC(CH3)3 (a) HI CF3CO,H, ? (b) H2O HI HI (c) Н,С— СНОСH,CH, (d) (CH3);CCH,OCH,CH3 H20 H2O
One step in the synthesis of the antihistamine fexofenadine (Section 23.5) involves acid-catalyzed hydration of the triple bond in A. Draw a stepwise mechanism for this reaction and explain why only ketone B is formed.
Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal antiinflammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib
Acetanilide is less reactive than aniline toward eletrophilic substitution. Explain.

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