Textbook Question
Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.
a. 3-phenylprop-1-ene
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 13c
Wade 9th EditionCh. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet SpectroscopyProblem 13cChapter 15, Problem 13c
Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.
c. dec-5-ene
Verified step by step guidance1
Step 1: Begin with bromobenzene as the starting material. Perform a Grignard reaction by reacting bromobenzene with magnesium (Mg) in dry ether to form phenylmagnesium bromide (a Grignard reagent). This will allow the phenyl group to act as a nucleophile in subsequent steps.
Step 2: To introduce the alkyl chain, react phenylmagnesium bromide with 1-bromobutane (an alkyl halide with four carbon atoms). This reaction will result in the formation of butylbenzene through a nucleophilic substitution mechanism.
Step 3: Perform a Friedel-Crafts alkylation on butylbenzene to extend the carbon chain. Use an alkyl halide such as 1-bromo-2-butene (a four-carbon alkenyl halide) in the presence of a Lewis acid catalyst like AlCl₃. This will introduce a double bond and form a longer alkyl chain attached to the benzene ring.
Step 4: Hydrogenate the benzene ring selectively to remove aromaticity and form a cyclohexane derivative. Use a catalyst such as Pd/C under hydrogen gas (H₂) to achieve this transformation.
Step 5: Perform a dehydrohalogenation reaction to form dec-5-ene. Use a strong base such as KOH or NaOH in an alcohol solvent to eliminate a halogen atom and form the desired alkene structure.
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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 context of synthesizing compounds from bromobenzene, understanding EAS is crucial as it allows for the introduction of various substituents onto the benzene ring, which can then be further manipulated to create desired products like dec-5-ene.
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EAS Review
Alkylation Reactions
Alkylation reactions involve the introduction of an alkyl group into a molecule, often through nucleophilic substitution or EAS. When synthesizing dec-5-ene, alkyl halides can be used to add carbon chains to the aromatic system or to create alkenes. Recognizing how to effectively use alkyl halides in these reactions is essential for constructing the target compound.
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03:19Sodium Alkynide Alkylation
Elimination Reactions
Elimination reactions are processes where two atoms or groups are removed from a molecule, resulting in the formation of a double bond. In the synthesis of dec-5-ene, elimination reactions can be employed after alkylation to generate the alkene from a saturated precursor. Understanding the conditions and mechanisms of elimination is vital for achieving the desired unsaturation in the final product.
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00:40Recognizing Elimination Reactions.
Related Practice
Textbook Question
Predict the products of the following proposed Diels–Alder reactions.
(b)
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Textbook Question
Predict the products of the following proposed Diels–Alder reactions.
(a)
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Textbook Question
Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.
b. 5-methylhex-2-ene
Textbook Question
Predict the products of the following proposed Diels–Alder reactions.
(c)
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Textbook Question
Addition of 1-bromobut-2-ene to magnesium metal in dry ether results in formation of a Grignard reagent. Addition of water to this Grignard reagent gives a mixture of but-1-ene and but-2-ene (cis and trans). When the Grignard reagent is made using 3-bromobut-1-ene, addition of water produces exactly the same mixture of products in the same ratios. Explain this curious result
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