Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.22P
For each pair of compounds:
base of each acid.
a.or b.or
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1.
b. Which is a stronger base?
2.
or
rank from weakest to strongest base (1 is weak while 3 is strong)
c
For each pair of compounds:
[1] Which indicated H is more acidic?
[2] Draw the conjugate base of each acid.
[3] Which conjugate base is stronger?
Chapter 2 Solutions
Organic Chemistry
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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- Summarize the relationship between pKa and acid strength by completing the following sentences: a. The higher the pKa of an acid, the stronger or weaker the acid. b. The lower the pKa of an acid, the stronger or weaker the acid.arrow_forwardDraw the structure of a constitutional isomer of compound B that fits each description. a. an isomer that is at least 105 times more acidic than B b. an isomer that is at least 10 times less acidic than B c. an isomer that is comparable in acidity to B HO. Barrow_forwardWhich compound in the following pair is the stronger acid? Select the single best answer. HO. Farrow_forward
- Draw the structure of a constitutional isomer of compound B that fits each description. a. an isomer that is at least 105 times more acidic than B b. an isomer that is at least 105 times less acidic than B c. an isomer that is comparable in acidity to Barrow_forwardWhich one is the strongest base?arrow_forwardIndicate the strongest acid for each pair of molecules: choose A or barrow_forward
- Answer the following questions about esmolol, a drug used to treat high blood pressure sold under the trade name Brevibloc.a.Label the most acidic hydrogen atom in esmolol. b.What products are formed when esmolol is treated with NaH? c. What products are formed when esmolol is treated with HCl? d.Label all sp2 hybridized C atoms. e. Label the only trigonal pyramidal atom. f. Label all C's that bear a δ+ charge.arrow_forwardAnswer the following questions about esmolol, a drug used to treat high blood pressure sold under the trade name Brevibloc.a.Label the most acidic hydrogen atom in esmolol. b.What products are formed when esmolol is treated with NaH? c.What products are formed when esmolol is treated with HCl? d. Label all sp2 hybridized C atoms. e.Label the only trigonal pyramidal atom. f.Label all C's that bear a δ+ charge.arrow_forward1. For each pair, predict which is the stronger base. Explain or or IZarrow_forward
- 2) Determine which molecule is the stronger base. a. b. NH2 Vs Vs NH NH CIarrow_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_forwardDraw the most stable conjugate base for each compund below (one hydrogen removed)arrow_forward
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