Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 2, Problem 2.52P
Interpretation Introduction
Interpretation: The reason for the lower
Concept introduction: The acidity of a compound is inversely related to the
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Rank the compound of the attached group from strongest acid to weakest acid:
Q17
Explain why phenol (C6H50H) is substantially
more acidic than methanol (CH3OH), but
benzoic acid (C6H5CO2H) is not much more
acidic than acetic acid (CH3CO2H).
Нас — ОН
ОН
H3C-
ОН
OH
pKa = 15.5
pKa = 10.0
pk = 4.75
pk = 4.2
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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- The following pKa values have been measured. Explain why a hydroxyl group in the para position decreases the acidity while a hydroxyl group in the meta position increases the acidity.arrow_forwardPQ-16. What is the major product of this reaction? OH (A) (B) 2) H3O+ H (C) (D) Harrow_forwardWhat is the structure of compound A? 010 Compound A tot 01 Oll O III O IV OV || s ||| Compound A IV COOHarrow_forward
- h) Which is a weaker base and why? Pyridine Pyrrole i) Name the following compounds. H2N A B NH2arrow_forwardWhich is more acidic, p-methylphenol or phenol? why? Why is water more acidic than ethanol but slightly less acidic than methanol? Explain the acidity trend of alcohols: 1>2 > 3arrow_forward16-26 The p/fb of amphetamine is approximately 3.2 Amphetamine (a) Which form of amphetamine (the free base or its conjugate acid) would you expect to be present at pH 1.0, the pH of stomach acid? (b ) Which form of amphetamine would you expect to be present at pH 7.40, the pH of blood plasma?arrow_forward
- Rank the following substances in order of increasing acidity: (a) (CH3)2CHOH, HC≡CH, (CF3)2CHOH, CH3OH (b) Phenol, p-methylphenol, p-[trifluoromethyl) phenol (c) Benzyl alcohol, phenol, p-hydroxybenzonic acidarrow_forwardWhen the conjugate acid of aniline, C6H5NH3+, reacts with the acetate ion, the following reaction takes place: C6H5NH3+(aq)+CH3COO(aq)C6H5NH2(aq)+CH3COOH(aq) If Kafor C6H5NH3+ is 1.35105 and Kafor CH3COOH is 1.86105 , what is K for the reaction?arrow_forward16-13 Classify each amino group as primary, secondary, or tertiary and as aliphatic or aromatic. Serotonin (a neurotransmitter) Diphenhydramine (the hydrochloride salt is the antihistamine Benadryl) Lysine (an amino acid)arrow_forward
- Calculate the Ka's for the following acids: (a) Citric acid, pKa = 3.14 (b) Tartaric acid, pKa = 2.98arrow_forwardBr NaoH NH2 H>N (B HYO what is compound A and B?arrow_forwardPhenol has a pka = 10.0. 4-Hydroxybenzaldehyde has a pka = 7.3. Draw resonance forms of the conjugate base of both and explain why 4-hydroxybenzaldehyde is more acidic. (Acidic H is underlined.) OH phenol OH -H* - H* 4-hyroxybenzaldehydearrow_forward
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