Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 25, Problem 25.37P
Varenicline (trade name Chantix) is a drug used to help smokers quit their habit. (a) Which
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Varenicline (trade name Chantix) is a drug used to help smokers quit their habit. (a) Which N atom in varenicline is most basic? Explain your choice. (b) What product is formed when varenicline is treated with HCl?
Rank the labeled nitrogen atoms in each compound in order of increasing basicity. Histamine causes the runny nose and watery eyes associated with allergies, and trazodone is a drug used as a sedative and antidepressant.
Rank the labeled N atoms in the anticancer drug imatinib (trade nameGleevec) in order of increasing basicity. Imatinib, sold as a salt withmethanesulfonic acid (CH3SO3H), is used for the treatment of chronicmyeloid leukemia as well as certain gastrointestinal tumors.
Chapter 25 Solutions
Organic Chemistry
Ch. 25 - Prob. 25.1PCh. 25 - Prob. 25.2PCh. 25 - Prob. 25.3PCh. 25 - Prob. 25.4PCh. 25 - Prob. 25.5PCh. 25 - Prob. 25.6PCh. 25 - Problem 25.7
Draw the product of each...Ch. 25 - Prob. 25.8PCh. 25 - Prob. 25.9PCh. 25 - Prob. 25.10P
Ch. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Problem 25.18
Write out steps to show how each of...Ch. 25 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Problem 25.22
Which nitrogen atom in each compound...Ch. 25 - Prob. 25.23PCh. 25 - Prob. 25.24PCh. 25 - Prob. 25.25PCh. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Problem 25.28
Draw the major product formed in...Ch. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Problem 25.31
Devise a synthesis of each compound...Ch. 25 - Prob. 25.32PCh. 25 - Problem 25.33
What starting materials are needed...Ch. 25 - Problem 25.34
(a) What two components are needed...Ch. 25 - Prob. 25.35PCh. 25 - Prob. 25.36PCh. 25 - 25.37 Varenicline (trade name Chantix) is a drug...Ch. 25 - Give a systematic or common name for each...Ch. 25 - Prob. 25.39PCh. 25 - 25.40 How many stereogenic centers are present in...Ch. 25 - 25.41 Rank the compounds in each group in order of...Ch. 25 - 25.42 Decide which atom in each molecule is most...Ch. 25 - 25.43 Explain why pyrimidine is less basic than...Ch. 25 - 25.44 Rank the nitrogen atoms in each compound in...Ch. 25 - 25.45 Explain why nitroaniline is a stronger base...Ch. 25 - 25.46 Explain the observed difference in the...Ch. 25 - 25.47 Why is pyrrole more acidic than...Ch. 25 - Prob. 25.48PCh. 25 - Prob. 25.49PCh. 25 - Prob. 25.50PCh. 25 - 25.51 How would you separate toluene , benzoic...Ch. 25 - 25.52 Draw the products formed when methylaniline ...Ch. 25 - Prob. 25.53PCh. 25 - Prob. 25.54PCh. 25 - 25.55 Draw the organic products formed in each...Ch. 25 - Prob. 25.56PCh. 25 - 25.57 Identify A, B, and C, three intermediates in...Ch. 25 - Prob. 25.58PCh. 25 - Prob. 25.59PCh. 25 - 25.60 A chiral amine A having the configuration...Ch. 25 - 25.61 Draw a stepwise mechanism for each...Ch. 25 - 25.62 Draw a stepwise mechanism for the following...Ch. 25 - Prob. 25.63PCh. 25 - 25.64 Tertiary aromatic amines react with and ...Ch. 25 - 25.65 Devise a synthesis of each compound from...Ch. 25 - Prob. 25.66PCh. 25 - Prob. 25.67PCh. 25 - Prob. 25.68PCh. 25 - Prob. 25.69PCh. 25 - 25.70 Devise a synthesis of each biologically...Ch. 25 - 25.71 Devise a synthesis of each compound from...Ch. 25 - 25.72 Three isomeric compounds A, B, and C, all...Ch. 25 - 25.73 Treatment of compound D with LiAlH4 followed...Ch. 25 - Prob. 25.74PCh. 25 - 25.75 Rank the following compounds in order of...Ch. 25 - Prob. 25.76PCh. 25 - Prob. 25.77PCh. 25 - Prob. 25.78P
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- Amphetamine is a powerful stimulant of the central nervous system. (a) Which proton in amphetamine is most acidic? (b) What products are formed when amphetamine is treated with NaH? (c) What products are formed when amphetamine is treated with HCl?arrow_forwardRank the given compounds in order of decreasing basicity. 1=most basic, 4=least basicarrow_forwardRank the compounds in each group in order of increasing basicity.arrow_forward
- Decide which N atom in each molecule is most basic and draw the product formed when each compound is treated with CH3CO2H. Zolpidem (trade name Ambien) is used to treat insomnia, whereas aripiprazole (trade name Abilify) is used to treat depression, schizophrenia, and bipolar disorders.arrow_forwardRank the labeled N atoms in the anticancer drug imatinib (trade name Gleevec) in order of increasing basicity. Imatinib, sold as a salt with methanesulfonic acid (CH3SO3H), is used for the treatment of chronic myeloid leukemia as well as certain gastrointestinal tumors.arrow_forwardRank the compounds in each group in order of increasing acidity.arrow_forward
- Caftaric acid is found in grapes, wine, and raisins. Rank the labeledprotons in caftaric acid in order of increasing acidity.arrow_forwardDecide which N atom in each molecule is most basic, and draw the product formed when each compound is treated with CH3CO2H. Zolpidem (trade name Ambien) is used to treat insomnia, whereasaripiprazole (trade name Abilify) is used to treat depression,schizophrenia, and bipolar disorders.arrow_forwardAnswer the following questions about erlotinib and terbinafine. Erlotinib,sold under the trade name Tarceva, was introduced in 2004 for thetreatment of lung cancer. Terbinafine is an antifungal medication used totreat ringworm and fungal nail infections. Which C–H bond in erlotinib is most acidic? What orbitals are used to form the shortest C–C single bond inerlotinib?arrow_forward
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