Textbook Question
Match four of the following UV absorption maxima (λmax) with the corresponding compounds: (1) 232 nm; (2) 256 nm; (3) 273 nm; (4) 292 nm; (5) 313 nm; (6) 353 nm.
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Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
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Wade 9th EditionCh. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet SpectroscopyProblem 25a
Wade 9th EditionCh. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet SpectroscopyProblem 25aChapter 15, Problem 25a
Predict the products of the following reactions.
(a) allyl bromide + cyclohexyl magnesium bromide
Verified step by step guidance1
Identify the type of reaction: This reaction involves an organometallic reagent (cyclohexyl magnesium bromide, a Grignard reagent) and an alkyl halide (allyl bromide). Grignard reagents typically act as nucleophiles in reactions with electrophiles.
Analyze the reactivity of the Grignard reagent: The cyclohexyl magnesium bromide contains a cyclohexyl group bonded to magnesium. The carbon attached to magnesium is highly nucleophilic due to the polar carbon-magnesium bond.
Determine the electrophilic site in allyl bromide: In allyl bromide, the carbon bonded to the bromine atom is electrophilic because bromine is more electronegative and withdraws electron density from the carbon.
Predict the nucleophilic attack: The nucleophilic cyclohexyl group from the Grignard reagent will attack the electrophilic carbon of allyl bromide, displacing the bromide ion (Br⁻) as a leaving group. This results in the formation of a new carbon-carbon bond.
Write the product structure: The product will be an alkane where the cyclohexyl group is bonded to the allyl group (CH₂=CH-CH₂). The bromide ion (Br⁻) is a byproduct of the reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the case of allyl bromide, the bromine atom acts as a leaving group, allowing the nucleophile (cyclohexyl magnesium bromide) to form a new bond with the carbon atom that was previously bonded to bromine.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Grignard Reagents
Grignard reagents are organomagnesium compounds that act as strong nucleophiles in organic reactions. Cyclohexyl magnesium bromide is a Grignard reagent that can react with electrophiles, such as allyl bromide, to form new carbon-carbon bonds. This reaction is crucial for building complex organic molecules and is a key tool in synthetic organic chemistry.
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Reaction Mechanism
Understanding the reaction mechanism is essential for predicting the products of organic reactions. In this case, the mechanism involves the nucleophilic attack of the Grignard reagent on the allyl bromide, leading to the formation of a new carbon-carbon bond. Analyzing the mechanism helps in anticipating the structure of the final product and understanding the steps involved in the reaction.
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Related Practice
Textbook Question
Predict the products of the following reactions.
(b) cyclopentadiene + anhydrous HCl
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Textbook Question
Predict the products of the following reactions.
(c) 2-methylpropene + NBS, light
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Textbook Question
Phenolphthalein is an acid–base indicator that is colorless below pH 8 and red above pH 8. Explain briefly why the first structure is colorless and the second structure is colored.
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Textbook Question
Predict the products of the following reactions.
(d) furan + trans-1,2-dicyanoethylene
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Textbook Question
Classify the following dienes and polyenes as isolated, conjugated, cumulated, or some combination of these classifications.
(a) cycloocta-1,4-diene
(b) cycloocta-1,3-diene
(c) cyclodeca-1,2-diene
(d) cycloocta-1,3,5,7-tetraene
(e) cyclohexa-1,3,5-triene (benzene)
(f) penta-1,2,4-triene