Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 15, Problem 20P
Suggest appropriate methods for preparing each of the following
Expert Solution & Answer
Interpretation Introduction
Interpretation:
The appropriate method of preparation for each of the given organometallic compounds is to be suggested.
Concept introduction:
The reaction of a metal with an organic halide is an oxidation–reduction in which the metal is the reducing agent.
lithium metal and magnesium metal in the presence of dry ether as a solvent, reacts with alkyl halides to produce the corresponding organo lithium and magnesium compounds respectively.
Organolithium reagents are used to prepare organometallic compounds analogous of terminal alkynes.
Organolithium compounds are strongly basic and react with terminal alkynes by abstracting the acidic proton and forming an alkane.
Answer to Problem 20P
Solution:
Explanation of Solution
Alkyl halides react with lithium metal in the presence of dry ether as a solvent to produce the corresponding organo lithium compound.
The product given is cyclopentyl lithium. Reaction of cyclopentyl bromide with lithium metal in the presence of diethyl ether as a solvent will produce this cyclopentyl lithium.
The reaction is shown below:
The product given is tert-butyl magnesium bromide. Tert-butyl bromide react with magnesium metal in the presence of diethyl ether as a solvent will produce this tert-butyl magnesium bromide.
The reaction is shown below:
Organolithium reagents are used to prepare organometallic compounds analogous of terminal alkynes.
Organolithium compounds are strongly basic and react with terminal alkynes by abstracting the acidic proton and forming an alkane.
Thus, phenyl acetylene reacts with an organo lithium reagent like butyl lithium to produce lithium phenylacetylide and butane.
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You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products:
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2. H₂O
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There is no reagent that will make this synthesis work without complications.
: ☐
S
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Predict the major products of this organic reaction:
H
OH
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Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry.
Click and drag to start drawing a
structure.
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For each reaction below, decide if the first stable organic product that forms in solution will create a new C-C bond, and check the appropriate box.
Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below.
Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first
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NH2
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?
Will the first product that forms in this reaction
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Yes
No
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Chapter 15 Solutions
Organic Chemistry - Standalone book
Ch. 15.1 - Each of the following organometallic reagents will...Ch. 15.3 - Write equations showing how you could prepare...Ch. 15.4 - Lithium diisopropylamide is often used as a strong...Ch. 15.5 - Write the structure of the organic product of each...Ch. 15.7 - Prob. 5PCh. 15.8 - Prob. 6PCh. 15.9 - Prob. 7PCh. 15.9 - Like nickel, iron reacts with carbon monoxide to...Ch. 15.9 - Prob. 9PCh. 15.9 - What is the oxidation state of manganese in the...
Ch. 15.9 - Prob. 11PCh. 15.10 - Prob. 12PCh. 15.10 - Prob. 13PCh. 15.11 - Give the structure including stereochemistry of...Ch. 15.11 - Prob. 15PCh. 15.12 - Homogeneous catalytic hydrogenation of the...Ch. 15.12 - Prob. 17PCh. 15.13 - What alkenes are formed from 2-pentene by olefin...Ch. 15.13 - The product of the following reaction was isolated...Ch. 15 - Suggest appropriate methods for preparing each of...Ch. 15 - Prob. 21PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 23PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 25PCh. 15 - A different stereoisomer of...Ch. 15 - Prob. 27PCh. 15 - Using phenyllithium and any necessary organic or...Ch. 15 - Prob. 29PCh. 15 - A number of drugs are prepared by reactions in...Ch. 15 - The following conversion was carried out in two...Ch. 15 - Outline syntheses of (a)...Ch. 15 - (S)-(+)-Ibuprofen can be prepared by...Ch. 15 - Like other hydroborations, the reaction of alkynes...Ch. 15 - The sex attractant of the female silkworm has been...Ch. 15 - Prob. 36PCh. 15 - (a) Exaltolide, a musk substance, has been...Ch. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and (Cyclobutadiene)tricarbonyliron...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...
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