Domanda del libro di testo
What is the product of the reaction of bromoethane with each of the following nucleophiles?
c. (CH3)3N
d. CH3CH2S-
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Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblema 15a,b
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblema 15a,bCapitolo 9, Problema 15a,b
What is the product of the reaction of bromoethane with each of the following nucleophiles?
a. CH3CH2CH2O−
b. CH3C≡C−
Guida verificata passo dopo passo1
Step 1: Recognize the type of reaction. The reaction of bromoethane (CH3CH2Br) with nucleophiles typically proceeds via an SN2 mechanism because bromoethane is a primary alkyl halide. In an SN2 reaction, the nucleophile attacks the electrophilic carbon (attached to the bromine) in a single concerted step, displacing the bromine as a leaving group.
Step 2: Analyze the first nucleophile (CH3CH2CH2O−). This is a strong nucleophile (an alkoxide ion). It will attack the electrophilic carbon in bromoethane, leading to the substitution of the bromine atom with the ethoxy group (CH3CH2CH2O−). The product will be CH3CH2CH2OCH2CH3 (propoxyethane).
Step 3: Analyze the second nucleophile (CH3C≡C−). This is an acetylide ion, which is also a strong nucleophile. It will similarly attack the electrophilic carbon in bromoethane, displacing the bromine atom. The product will be CH3C≡CCH2CH3 (butyne).
Step 4: Consider the stereochemistry. Since the SN2 mechanism involves a backside attack, the configuration of the carbon center (if it were chiral) would invert. However, in this case, bromoethane is not chiral, so stereochemistry is not a concern.
Step 5: Summarize the products. For part (a), the product is propoxyethane (CH3CH2CH2OCH2CH3). For part (b), the product is butyne (CH3C≡CCH2CH3). These products result from the substitution of bromine with the respective nucleophiles.
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Nucleophilicity
Nucleophilicity refers to the ability of a species to donate an electron pair to an electrophile, forming a chemical bond. Strong nucleophiles, such as alkoxide ions (like CH3CH2CH2O−), are more likely to react with electrophiles like bromoethane. The strength of a nucleophile is influenced by factors such as charge, electronegativity, and steric hindrance.
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Nucleophilic Addition
Substitution Reactions
Substitution reactions involve the replacement of one functional group in a molecule with another. In the case of bromoethane, the bromine atom can be replaced by a nucleophile through either an SN1 or SN2 mechanism, depending on the structure of the nucleophile and the substrate. Understanding these mechanisms is crucial for predicting the products of the reaction.
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01:34Recognizing Substitution Reactions.
Alkyl Halides
Alkyl halides, such as bromoethane, are organic compounds containing a carbon-halogen bond. They are key substrates in nucleophilic substitution reactions. The reactivity of alkyl halides is influenced by the type of halogen, the carbon's hybridization, and the presence of steric factors, which can affect the pathway of the reaction with nucleophiles.
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01:52How to name alkyl halides
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