Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
Question
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Chapter 2, Problem 2.70P
Interpretation Introduction

Interpretation:

To explain the difference in the observed pK values for P and Q.

Concept introduction:

Acid base reaction or Proton transfer reaction. It is the equilibrium reaction. An acid donates a proton to a based and thus forming conjugate acid and base. The reaction is always involves two acid and bases. It is equilibrium reaction so the position of the equilibrium depends on the strength of the acid and bases. The stronger is the acid that donates proton and the stronger base accept the proton. Then these two forms the conjugate acid and base as shown below in the Fig.

Organic Chemistry-Package(Custom), Chapter 2, Problem 2.70P

From the Bronsted-Lowry, an acid is a proton donor and from the Lewis electron pairs acceptor. Thus an acid strength is defined as the tendency to donate proton. The decision of an acid is stronger is based on the compound donating proton. If the compound readily donates the proton then it is strong acid. The strong acid is determined using the acidity constant, Ka. So larger the Ka value stronger the acid. Moreover for exponent value it is conveniently measured by pKa values.

pKa = -log Ka

So, smaller the pKa, stronger is the acid.

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Chapter 2 Solutions

Organic Chemistry-Package(Custom)

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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