Textbook Question
For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:
d.
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Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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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
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Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 67c
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 67cChapter 10, Problem 67c
What product is formed when 1-bromopropane reacts with each of the following nucleophiles?
c. CH3S−
Verified step by step guidance1
Identify the type of reaction: This is a nucleophilic substitution reaction, where the nucleophile (CH3S−) will attack the electrophilic carbon in 1-bromopropane, displacing the bromine atom.
Analyze the substrate: 1-bromopropane is a primary alkyl halide, which typically undergoes an SN2 mechanism due to the lack of steric hindrance around the electrophilic carbon.
Understand the nucleophile: CH3S− is a strong nucleophile because sulfur is less electronegative than oxygen, making it more polarizable and better at donating its lone pair of electrons.
Describe the mechanism: In the SN2 mechanism, the nucleophile (CH3S−) attacks the carbon bonded to the bromine atom from the opposite side (backside attack), leading to the simultaneous displacement of the bromine atom as a leaving group.
Write the product: The nucleophile (CH3S−) replaces the bromine atom, forming the product CH3CH2CH2SCH3 (propyl methyl sulfide).
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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 replaces a leaving group in a molecule. In this context, 1-bromopropane, which contains a bromine leaving group, can undergo substitution when reacted with a nucleophile like CH3S−. The mechanism can follow either an SN1 or SN2 pathway, depending on the structure of the substrate and the nucleophile's strength.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Nucleophiles
Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. They are typically negatively charged or neutral molecules with lone pairs of electrons. In this case, CH3S− is a strong nucleophile due to the presence of a sulfur atom, which has a high electron density, making it effective in attacking the electrophilic carbon in 1-bromopropane.
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Product Formation
The product formed from the reaction of 1-bromopropane with CH3S− is propyl thioether (CH3CH2CH2SCH3). This occurs as the nucleophile attacks the carbon atom bonded to the bromine, displacing the bromine atom and forming a new C-S bond. Understanding the nature of the product is crucial for predicting the outcome of nucleophilic substitution reactions.
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Related Practice
Textbook Question
Which member of each pair is a better nucleophile in methanol?
e. I− or Br−
f. Cl− or Br−
1149
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Textbook Question
Which member in each pair in [PROBLEM 9-68] is a better leaving group?
a. H2O or HO−
b. NH3 or H2O
754
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Textbook Question
For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:
c.
1125
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Textbook Question
For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:
b.
711
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Textbook Question
What product is formed when 1-bromopropane reacts with each of the following nucleophiles?
d. HS−
2218
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