ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS
ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS
6th Edition
ISBN: 9781260325294
Author: SMITH
Publisher: RENT MCG
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Chapter 2, Problem 36P

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 ?

Chapter 2, Problem 36P, 2.36 Propranolol is an antihypertensive agent—that is, it lowers blood pressure. (a) 
Which proton

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The most acidic proton in propranolol is to be identified.

Concept introduction: An acid is a substance that is capable to donate H+ ions or protons. The loss of a proton by an acid results in the formation of a substance known as conjugate base and the gain of a proton by a base results in the formation of a substance known as conjugate acid. The acidity of an acid is directly proportional to the resonance stabilization of its conjugate base.

Answer to Problem 36P

The most acidic proton is H of O····H group.

Explanation of Solution

The given ball-and-stick model of propranolol is,

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 2, Problem 36P , additional homework tip  1

Figure 1

In ball-and-stick model, each colored ball represents a specific atom and each stick represents a bond. In this model, each black ball represents C atom, each gray ball represents H atom, each blue ball represents N atom and each red ball represents O atom.

Thus, the given compound is drawn as,

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 2, Problem 36P , additional homework tip  2

Figure 2

The acidity of an acid is directly proportional to the resonance stabilization of its conjugate base. In propranolol, when the O····H group losses a proton it forms a conjugate base that is much more resonance stabilized.

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 2, Problem 36P , additional homework tip  3

Figure 3

Thus, the most acidic proton is H of O····H group.

Conclusion

The most acidic proton is H of O····H group.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of propranolol with NaH are to be stated.

Concept introduction: Sodium hydride (NaH) is a metal hydride. It is a strong base. It abstracts the most acidic proton and forms alkoxide ion. The resultant ion is a conjugate base of parent one (alcohol).

Answer to Problem 36P

The product formed by the treatment of propranolol with NaH is,

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 2, Problem 36P , additional homework tip  4

Explanation of Solution

Sodium hydride (NaH) is a metal hydride. It is a strong base. It abstracts the most acidic proton and forms alkoxide ion. The formed ion is a conjugate base of parent one (alcohol).

The products formed by the treatment of propranolol with NaH are shown in Figure 4.

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 2, Problem 36P , additional homework tip  5

Figure 4

Conclusion

The product formed by the treatment of propranolol with NaH is an alkoxide ion.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The most basic atom in propranolol is to be identified.

Concept introduction: A base is a substance that is capable to accept a H+ ion or a proton. The nitrogen atom of NH bond is more basic than the oxygen atom of OH bond. It is due to less electronegativity of nitrogen than that of oxygen atom. Moreover, the conjugate base of OH group is much more resonance stabilized.

Answer to Problem 36P

The most basic atom is N of N··H group.

Explanation of Solution

A base is a substance that is capable to accept H+ ion or hydrogen ion. The nitrogen atom of NH bond is more basic than the oxygen atom of OH bond. It is due to less electronegativity of nitrogen than that of oxygen atom. Moreover, the conjugate base of OH group is much more resonance stabilized than the N··H group.

Thus, the most basic atom is N of N··H group.

Conclusion

The most basic atom is N of N··H group.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The products formed by the treatment of propranolol with HCl are to be stated.

Concept introduction: Hydrogen chloride (HCl) is a halogen acid. It is a strong acid. It donates H+ ion to the most basic atom and forms a salt (includes halogen atom).

Answer to Problem 36P

The product formed by the treatment of propranolol with HCl is,

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 2, Problem 36P , additional homework tip  6

Explanation of Solution

Hydrogen chloride (HCl) is a halogen acid. It is a strong acid. It donates H+ ion to the most basic atom and forms a salt (includes halogen atom).

The product formed by the treatment of propranolol with HCl is shown in Figure 5.

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 2, Problem 36P , additional homework tip  7

Figure 5

Conclusion

The product formed by the treatment of propranolol with HCl is a salt.

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Chapter 2 Solutions

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS

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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