ORGANIC CHEMISTRY W/ALEKS
6th Edition
ISBN: 9781264905430
Author: SMITH
Publisher: MCG CUSTOM
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Textbook Question
Chapter 2, Problem 37P
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
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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?
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.
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?
Chapter 2 Solutions
ORGANIC CHEMISTRY W/ALEKS
Ch. 2.1 - a. Which compounds are Bronsted-Lowry acids:...Ch. 2.2 - a. Draw the conjugate acid of each base:...Ch. 2.2 - Label each statement as True or False.
a. is the...Ch. 2.2 - Decide which compound is the acid and which is the...Ch. 2.2 - Draw the products formed from the acid-base...Ch. 2.3 - Which compound in each pair is the stronger acid?...Ch. 2.3 - Use a calculator when necessary to answer the...Ch. 2.3 - Rank the conjugate bases of each of group of acids...Ch. 2.3 - Problem-2.10 Considers two acids: (formic acid,)...Ch. 2.3 - Prob. 11P
Ch. 2.4 - Draw the products of each reaction and determine...Ch. 2.4 - Prob. 13PCh. 2.5 - Without reference to a pKa table, decide which...Ch. 2.5 - Rank the labeled H atoms in the following compound...Ch. 2.5 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2.5 - Which compound in each pair is the stronger acid?...Ch. 2.5 - Glycolic acid, HOCH2CO2H, is the simplest member...Ch. 2.5 - Explain the apparent paradox. HBr is a stronger...Ch. 2.5 - The CH bond in acetone, (CH3)2C=O, has a pKa of...Ch. 2.5 - Prob. 23PCh. 2.5 - For each pair of compounds: [1] Which indicated H...Ch. 2.5 - Rank the compounds in each group in order of...Ch. 2.5 - Prob. 26PCh. 2.5 - Prob. 27PCh. 2.6 - Prob. 28PCh. 2.7 - Problem 2.29
Compounds like amphetamine that...Ch. 2.8 - Problem 2.30 Which species are Lewis bases?
a. b....Ch. 2.8 - Which species are Lewis acids?
a. b. c. d.
Ch. 2.8 - For each reaction, label the Lewis acid and base....Ch. 2.8 - Prob. 33PCh. 2.8 - Prob. 34PCh. 2.8 - Label the Lewis acid and base. Use curved arrow...Ch. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - 2.38 What is the conjugate acid of each base?
a....Ch. 2 - 2.39 What is the conjugate base of each acid?
a....Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Prob. 43PCh. 2 - What is Ka for each compound? Use a calculator...Ch. 2 - What is the pKa for each compound? a. b. c.Ch. 2 - Which of the following bases are strong enough to...Ch. 2 - Draw the products of each reaction. Use the pKa...Ch. 2 - a. What is the conjugate acid of A? b. What is the...Ch. 2 - Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH)...Ch. 2 - 2.59 Atenolol is a (beta) blocker, a drug used to...Ch. 2 - 2.60 Use the principles in Section 2.5 to label...Ch. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 66PCh. 2 - 2.63 Classify each compound as a Lewis base, a...Ch. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Label the Lewis acid and Lewis base in each...Ch. 2 - 2.66 Draw the products of each Lewis acid-base...Ch. 2 - Prob. 71PCh. 2 - 2.68 Answer the following questions about the four...Ch. 2 - Prob. 73PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - Prob. 76PCh. 2 - Prob. 77PCh. 2 - Prob. 82P
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- Varenicline (trade name Chantix) is a drug used to help smokers quittheir habit. (a) Which N atom in varenicline is most basic? Explain your choice. (b) What product is formed when varenicline is treated with HCl?arrow_forwardAmphetamine is a powerful stimulant of the central nervous system.Draw the products formed (and show the flow of electrons) from the acid-base reaction of amphetamine with (a) HCl and with (b) NaH.arrow_forwardWrite an equation for the acid-base equilibrium of:(a) Pyrrolidine and water (b) Pyridine and waterarrow_forward
- Caftaric acid is found in grapes, wine, and raisins. Rank the labeledprotons in caftaric acid in order of increasing acidity.arrow_forwardA carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.(a) Draw the resonance forms of a carboxylic acid that is protonated on the hydroxyoxygen atom.(b) Compare the resonance forms with those given previously for an acid protonated on thecarbonyl oxygen atomarrow_forwardExplain why phenol is more acidic than alcohols by considering the resonance effect anddrawing the resonance structures of phenoxide ions.arrow_forward
- 18.64 The following two compounds each exhibit two heteroatoms (one nitrogen atom and one oxygen atom). :0 Compound A -N Compound B O In compound A, the lone pair on the nitrogen atom is more likely to function as a base. However, in compound B, the lone pair on the oxygen atom is more likely to function as a base. Explain this difference.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
- Consider the following reaction: (a) What is the acid on the left side of the equation? (b) What is the base on the left side of the equation? (c) What is the conjugate base of the acid on the left? (d) What is the conjugate acid of the base on the left? (e) What is the acid on the right side of the equation? (f) What is the base on the right side of the equation? (g) What is the conjugate base of the acid on the right? (h) What is the conjugate acid of the base on the right?arrow_forwardBupivacaine (trade name Marcaine) is a quick-acting anesthetic oftenused during labor and delivery. Which nitrogen atom in bupivacaine ismore basic? Explain your reasoning.arrow_forwardList the following compounds by discussing their basicity.arrow_forward
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