Textbook Question
Which of following ethers cannot be made by a Williamson ether synthesis?
1460
views
Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides
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. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 99e
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 99eChapter 10, Problem 99e
What are the products of the following reactions?
e. 
Verified step by step guidance1
Step 1: Identify the type of reaction. The given reaction involves a primary alkyl bromide (1-bromobutane) and a strong nucleophile/base (methoxide ion, CH3O−). This setup suggests an SN2 reaction mechanism due to the primary nature of the alkyl halide.
Step 2: Understand the SN2 mechanism. In an SN2 reaction, the nucleophile attacks the electrophilic carbon (the carbon bonded to the bromine) from the opposite side of the leaving group, resulting in a single-step substitution reaction.
Step 3: Determine the leaving group. Bromine (Br) is the leaving group in this reaction. It will depart as Br−, leaving the carbon atom available for nucleophilic attack.
Step 4: Predict the product. The methoxide ion (CH3O−) will replace the bromine atom on the carbon chain, forming an ether. The product will be butyl methyl ether (CH3OCH2CH2CH2CH3).
Step 5: Verify stereochemistry. Since the reaction follows an SN2 mechanism, the attack by the nucleophile will invert the configuration at the carbon center if it is chiral. However, in this case, the carbon is not chiral, so stereochemistry is not a concern.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
5mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Elimination Reactions
Elimination reactions involve the removal of a small molecule from a larger one, resulting in the formation of a double bond. In this case, the bromide (Br) is eliminated along with a proton (H) from an adjacent carbon, leading to the formation of an alkene. Understanding the mechanism of elimination, such as E2 or E1, is crucial for predicting the products.
Recommended video:
Guided course
00:40
Recognizing Elimination Reactions.
Nucleophiles and Their Role
Nucleophiles are species that donate an electron pair to form a chemical bond. In this reaction, methoxide (CH3O-) acts as a strong nucleophile, attacking the carbon atom bonded to the bromine. This interaction is essential for driving the elimination process and determining the final products of the reaction.
Recommended video:
Guided course
08:27Nucleophilic Addition
Regioselectivity in Elimination
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others. In elimination reactions, the location of the double bond formed can vary, leading to different products. Factors such as sterics and the stability of the resulting alkene influence which product is favored, making it important to analyze the structure of the starting material.
Recommended video:
Guided course
00:38Intro to Substitution/Elimination Problems
Related Practice
Textbook Question
What are the products of the following reactions?
g.
h.
1172
views
Textbook Question
What are the products of the following reactions?
a.
b.
1302
views
Textbook Question
When 2-bromo-2,3-dimethylbutane reacts with a strong base, two alkenes (2,3-dimethyl-1-butene and 2,3-dimethyl-2-butene) are formed.
a. Which of the bases (A, B, C, or D) would form the highest percentage of the 1-alkene?
b. Which would give the highest percentage of the 2-alkene?
2255
views
Textbook Question
What are the products of the following reactions?
f.
1338
views
Textbook Question
a. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol.
b. Are all the products optically active?
1622
views