Textbook Question
One of the following compounds undergoes electrophilic aromatic substitution predominantly at C-3, and one undergoes electrophilic aromatic substitution predominantly at C-4. Which is which?
757
views
Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Bruice 8th EditionCh. 19 - More About Amines • Reactions of Heterocyclic CompoundsProblem 30a,b
Bruice 8th EditionCh. 19 - More About Amines • Reactions of Heterocyclic CompoundsProblem 30a,bChapter 20, Problem 30a,b
Name the following:
a. 
b. 
Verified step by step guidance1
Step 1: Analyze the structure in part (i). The molecule contains a pyridine ring (a six-membered aromatic ring with one nitrogen atom) substituted with a bromine atom and an ethyl group. Identify the positions of the substituents relative to the nitrogen atom in the pyridine ring.
Step 2: Assign locants to the substituents in part (i). The nitrogen atom in the pyridine ring is position 1. The bromine atom is at position 3, and the ethyl group is at position 4. Use the lowest possible locants for naming.
Step 3: Combine the substituents and the parent name for part (i). The parent name is 'pyridine,' and the substituents are '3-bromo' and '4-ethyl.' Assemble the name in alphabetical order of the substituents.
Step 4: Analyze the structure in part (ii). The molecule contains a piperidine ring (a six-membered saturated ring with one nitrogen atom) substituted with a methyl group and an ethyl group. Identify the positions of the substituents relative to the nitrogen atom in the piperidine ring.
Step 5: Assign locants to the substituents in part (ii). The nitrogen atom in the piperidine ring is position 1. The methyl group is at position 2, and the ethyl group is at position 4. Use the lowest possible locants for naming. Combine the substituents and the parent name 'piperidine' in alphabetical order.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Benzene Derivatives
Benzene derivatives are compounds that contain a benzene ring, which is a six-carbon ring with alternating double bonds. The presence of substituents, such as halogens or functional groups, can significantly alter the chemical properties and reactivity of the benzene ring. Understanding how to identify and name these derivatives is crucial in organic chemistry.
Recommended video:
Guided course
02:49
Aromatic synthesis starting with benzene/benzene derivatives
Nomenclature of Organic Compounds
Nomenclature refers to the systematic naming of organic compounds according to established rules, such as those set by the International Union of Pure and Applied Chemistry (IUPAC). This includes identifying the longest carbon chain, naming substituents, and determining the correct numbering of the carbon atoms to provide a unique and informative name for each compound.
Recommended video:
Guided course
01:40Defining meso compounds.
Substituent Effects
Substituent effects describe how different groups attached to a benzene ring can influence its reactivity and stability. For example, electron-donating groups can activate the ring towards electrophilic substitution, while electron-withdrawing groups can deactivate it. Recognizing these effects is essential for predicting the behavior of benzene derivatives in chemical reactions.
Recommended video:
2:02Directing Effects in Substituted Pyrroles, Furans, and Thiophenes Concept 1
Related Practice
Textbook Question
Benzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a Lewis acid such as AlCl3.
a. What are the major and minor products of the following reaction?
b. Would you expect epoxides to undergo similar reactions?
1382
views
Textbook Question
Name the following:
c.
889
views
Textbook Question
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
a.
b.
652
views
Textbook Question
A tertiary amine reacts with hydrogen peroxide to form a tertiary amine oxide.
Tertiary amine oxides undergo a reaction similar to the Hofmann elimination reaction (Section 10.10), called a Cope elimination. In this reaction, a tertiary amine oxide, rather than a quaternary ammonium ion, undergoes elimination. A strong base is not needed for a Cope elimination because the amine oxide acts as its own base.
Does the Cope elimination have an alkene-like transition state or a carbanion-like transition state?
1376
views
Textbook Question
Pyrrole reacts with excess para-(N,N-dimethylamino)benzaldehyde to form a highly colored compound. Draw the structure of the colored compound.
1000
views