Textbook Question
Draw the product from reaction of the following substances with (1) Br2 and FeBr3 and (2) SO3 and H2SO4 catalyst (red=O):
(a) <IMAGE>
(b) <IMAGE>
Ch.13 Alkenes, Alkynes, and Aromatic Compounds
McMurry8th EditionFundamentals of GOBISBN: 9780134015187
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Table of contents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
Chapter 13, Problem 23
Reaction of Br2 and FeBr3 with phenol can lead to three possible substitution products. Show the structure of each and name them.
Verified step by step guidance1
Phenol (C6H5OH) is an aromatic compound with an -OH group attached to the benzene ring. The -OH group is an activating group, meaning it directs electrophilic substitution reactions to the ortho and para positions of the benzene ring.
The reaction involves bromine (Br2) in the presence of a catalyst, FeBr3. FeBr3 acts as a Lewis acid, polarizing the Br2 molecule and generating the electrophile, Br⁺, which will attack the benzene ring.
The first possible product is the ortho-substituted product, 2-bromophenol. This occurs when the Br⁺ electrophile substitutes at the position adjacent to the -OH group on the benzene ring.
The second possible product is the para-substituted product, 4-bromophenol. This occurs when the Br⁺ electrophile substitutes at the position opposite the -OH group on the benzene ring.
The third possible product is the di-substituted product, 2,4-dibromophenol. This occurs when two Br⁺ electrophiles substitute at both the ortho and para positions relative to the -OH group. The structure of each product can be drawn by placing the Br atoms at the respective positions on the benzene ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the case of phenol, the hydroxyl group (-OH) activates the ring, making it more reactive towards electrophiles like Br2 and FeBr3. Understanding EAS is crucial for predicting the products formed when phenol reacts with bromine.
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Naming Alkanes with Substituents Example 1
Bromination of Phenol
Bromination of phenol involves the introduction of bromine atoms into the aromatic ring. The reaction can yield multiple products depending on the position of substitution, typically ortho and para to the hydroxyl group. Recognizing the regioselectivity of bromination is essential for identifying the specific substitution products formed in this reaction.
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Substitution Product Structures
The substitution products of phenol with bromine include ortho-bromophenol, para-bromophenol, and brominated phenol derivatives. Each product has a distinct molecular structure based on the position of the bromine atom relative to the hydroxyl group. Drawing and naming these structures is vital for a complete understanding of the reaction outcomes.
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Related Practice
Textbook Question
Draw the structures of the two different alkenes from which 3-methyl-3-pentanol, shown in the margin, can be made. Draw them in both condensed and line format.
Textbook Question
The structure of vinyl acetate is shown below (the partial structure H2C=CH-is known as a vinyl group). When polymerized it produces poly(vinyl acetate), a polymer used for the springy soles in running shoes. Draw the structure of the polymer obtained if three vinyl acetate units underwent polymerization.
Textbook Question
Draw structures corresponding to the following names (refer to Table 13.2 if necessary):
a. m-Chloronitrobenzene
b. o-Nitrotoluene
c. p-Methylaniline
d. p-Nitrophenol
Textbook Question
Alkynes undergo hydrogenation to give alkanes, just as alkenes do. Draw and name the products that would result from hydrogenation of the alkynes shown in Problem 13.25.
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Textbook Question
What do the terms saturated and unsaturated mean?