Textbook Question
From which of the following compounds can HO− remove a proton in a reaction that favors product formation?
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Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 66
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 66Chapter 3, Problem 66
Tenormin, a member of the group of drugs known as beta-blockers, is used to treat high blood pressure and improve survival after a heart attack. It works by slowing down the heart to reduce its workload. Which atom in Tenormin is the most basic?
Verified step by step guidance1
Step 1: Understand the concept of basicity in organic chemistry. Basicity refers to the ability of an atom to donate a pair of electrons, typically to a proton (H⁺). Atoms with lone pairs of electrons, such as nitrogen, oxygen, or sulfur, are often candidates for basicity.
Step 2: Analyze the structure of Tenormin (Atenolol). Tenormin contains functional groups such as amines, alcohols, and possibly ethers. Focus on identifying atoms with lone pairs of electrons that can act as bases.
Step 3: Evaluate the nitrogen atom in the amine group. Amines are typically more basic than oxygen-containing groups because nitrogen is less electronegative than oxygen, making its lone pair more available for protonation.
Step 4: Consider the environment around the nitrogen atom. If the nitrogen is part of a secondary or tertiary amine, its basicity may be influenced by steric hindrance or electronic effects from nearby groups.
Step 5: Compare the basicity of the nitrogen atom to other atoms in the molecule, such as oxygen in alcohol or ether groups. Oxygen atoms are generally less basic than nitrogen due to their higher electronegativity, which holds onto the lone pair more tightly.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Basicity in Organic Chemistry
Basicity refers to the ability of a compound to accept protons (H+) or donate electron pairs. In organic chemistry, basicity is influenced by the structure of the molecule, including the presence of electronegative atoms and the availability of lone pairs. A more basic atom typically has a higher electron density and is less hindered by steric factors.
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Functional Groups in Beta-Blockers
Beta-blockers, like Tenormin, contain specific functional groups that influence their pharmacological properties. Common functional groups include amines, which can act as bases due to the presence of nitrogen atoms with lone pairs. Understanding the functional groups present in Tenormin is crucial for determining which atom may exhibit the highest basicity.
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Structure-Activity Relationship (SAR)
The Structure-Activity Relationship (SAR) is a principle that explores how the chemical structure of a compound relates to its biological activity. In the case of Tenormin, analyzing its molecular structure helps identify which atoms contribute to its basicity and overall effectiveness as a beta-blocker. This relationship is essential for predicting how modifications to the structure can affect drug performance.
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Related Practice
Textbook Question
For each of the following pairs of reactions, indicate which one has the more favorable equilibrium constant (that is, which one most favors products):
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2.
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Textbook Question
b. Determine the exact pKa values, using a calculator.
c. Which is the strongest acid?
1. nitrous acid (HNO2), Ka = 4.0 × 10−4
2. nitric acid (HNO3), Ka = 22
3. bicarbonate (HCO3−), Ka = 6.3 × 10−11
4. hydrogen cyanide (HCN), Ka = 7.9 × 10−10
5. formic acid (HCOOH), Ka = 2.0 × 10−4
6. phosphoric acid (H3PO4), Ka = 2.1
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Textbook Question
Given the Ka values, estimate the pKa value of each of the following acids without using a calculator (that is, is it between 3 and 4, between 9 and 10, and so on?):
1. nitrous acid (HNO2), Ka = 4.0 × 10−4
2. nitric acid (HNO3), Ka = 22
3. bicarbonate (HCO3−), Ka = 6.3 × 10−11
4. hydrogen cyanide (HCN), Ka = 7.9 × 10−10
5. formic acid (HCOOH), Ka = 2.0 × 10−4
6. phosphoric acid (H3PO4), Ka = 2.1
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Textbook Question
For each compound, indicate the atom that is most apt to be protonated.
a.
b.
c.
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Textbook Question
Which of the four reactions has the most favorable equilibrium constant?
1.
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