Organic Chemistry - With Access (Custom)
4th Edition
ISBN: 9781259147760
Author: OHIO UNIV.
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.34P
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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Propranolol is an antihypertensive agent – that is, it lowers blood pressure. (a) Which proton in propranolol is most acidic? (b) What products are formed when propranolol is treated with NaH? (c) Which atom is most basic? (d) What products are formed when propranolol is treated with HCl?
Rank the attached compounds in order of increasing acidity, and then ranktheir conjugate bases in order of increasing basicity ?
Choose in each set the most acidic compound. Give explanation.
Chapter 2 Solutions
Organic Chemistry - With Access (Custom)
Ch. 2 - a. Which compounds are Bronsted-Lowry acids:...Ch. 2 - a. Draw the conjugate acid of each base:...Ch. 2 - Label the acid and base, and the conjugate acid...Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Which compound in each pair is the stronger acid?...Ch. 2 - Use a calculator when necessary to answer the...Ch. 2 - Rank the conjugate bases of each of group of acids...Ch. 2 - Problem-2.10 Considers two acids: (formic acid,)...Ch. 2 - Estimate the pKa of each of the indicated bonds.
Ch. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.12PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - which compound in each pair of isomers is the...Ch. 2 - Prob. 2.15PCh. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - whichcompound in each pair is the stronger acid? a...Ch. 2 - Glycolic acid, HOCH2CO2H, is the simplest member...Ch. 2 - Explain the apparent paradox. HBr is a stronger...Ch. 2 - The CH bond in acetone, (CH3)2C=O, has a pKa of...Ch. 2 - Acetonitrile (CH3CN) has a pKa of 25, making it...Ch. 2 - For each pair of compounds: [1] Which indicated H...Ch. 2 - Rank the compounds in each group in order of...Ch. 2 - Which proton in each of the following drugs is...Ch. 2 - Prob. 2.25PCh. 2 - Problem 2.29
Compounds like amphetamine that...Ch. 2 - Problem 2.30 Which species are Lewis bases?
a. b....Ch. 2 - Which species are Lewis acids?
a. b. c. d.
Ch. 2 - For each reaction, label the Lewis acid and base....Ch. 2 - Prob. 2.30PCh. 2 - Prob. 2.31PCh. 2 - Prob. 2.32PCh. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - Prob. 2.35PCh. 2 - Prob. 2.36PCh. 2 - a Draw the conjugate acid of ethylene, CH2 = CH2....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Prob. 2.40PCh. 2 - Draw the product of acid-base reaction. a. c. b....Ch. 2 - Prob. 2.42PCh. 2 - Prob. 2.43PCh. 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 - Which compounds can be deprotonated by OH, so that...Ch. 2 - Draw the product of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - Rank the following ions in order of increasing...Ch. 2 - Prob. 2.51PCh. 2 - Prob. 2.52PCh. 2 - The pKa of three CH bonds is given below. a. For...Ch. 2 - a. What is the conjugate acid of A? b. What is the...Ch. 2 - 2.56 Draw the structure of a constitutional isomer...Ch. 2 - 2.57 Many drugs are Bronsted-Lowry acids or...Ch. 2 - Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH)...Ch. 2 - Prob. 2.58PCh. 2 - Ethyl butanoate, CH3CH2CH2CO2CH2CH3, is one of the...Ch. 2 - Prob. 2.60PCh. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Prob. 2.64PCh. 2 - Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.66PCh. 2 - Prob. 2.67PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - Prob. 2.70PCh. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Two pKa values are reported for malonic acid, a...Ch. 2 - Prob. 2.74PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.76PCh. 2 - 2.78 Which compound, M or N, is the stronger acid?...
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- Place the following compounds in order of relative acidity. Consider 1 to be the most acidic and 6 to be the least acidic.arrow_forwardA. Compound II is more basic than compound I. B. Compound I is more basic than compound II. C. Cannot be compared D. Both compounds have the same basicityarrow_forwardplease explain and rank the following compound in order of increasing acidityarrow_forward
- Answer the following questions about the four species A–D.a.Which two species represent a conjugate acid–base pair? b. Which two species represent resonance structures? c. Which two species represent constitutional isomers?arrow_forwardDraw the structure of a constitutional isomer of compound B that fitseach description.a.) an isomer that is at least 105 times more acidic than Bb.) an isomer that is at least 105 times less acidic than Bc.) an isomer that is comparable in acidity to Barrow_forwardThe order of increasing acidity is Phenol < meta-cyanophenol < ortho-cyanophenol 1.how about para-cyanophenol??does it has higher acidicity than both ortho-cyanophenol and meta cyanophenol or lower?? 2.why does ortho-cyanophenol have higher acidicity than meta cyanophenol?? 3. why doesmeta cyanophenol have higher acidicity than Phenolarrow_forward
- Ibuprofen is A. the same acidity as potassium hydrogen phthalate B. less acidic than phenolphthalein C. less acidic than potassium hydrogen phthalate D. more acidic than potassium hydrogen phthalatearrow_forwardRank the bases below in order of increasing basicity.arrow_forwardRank the following substances in order of increasing acidity:arrow_forward
- Arrange each group of compounds in order of increasing acidity.butyric acid, a@bromobutyric acid, b@bromobutyric acidarrow_forwardRank 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.arrow_forwardPropoxide (CH3CH2CH2O- ) is a larger molecule than ethoxide (CH3CH2O- ), yet they are equally basic. Explain why they are equally basic.arrow_forward
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