Textbook Question
Predict the products of the following reactions.
(c)
(d)
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Ch.10 - Structure and Synthesis of Alcohols
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
Chapter 10, Problem 11a-h
Which of the following compounds are suitable solvents for Grignard reactions?
(a) n-hexane
(b) CH3–O–CH3
(c) CHCl3
(d) cyclohexane
(e) benzene
(f) CH3OCH2CH2OCH3
(g) 
(h) 
Verified step by step guidance1
Step 1: Understand the requirements for a solvent to be suitable for Grignard reactions. Grignard reagents are highly reactive and can be destroyed by protic solvents or solvents containing acidic hydrogen atoms. Suitable solvents must be aprotic and non-reactive with the Grignard reagent.
Step 2: Analyze each compound provided in the list. For example, n-hexane (a) and cyclohexane (d) are non-polar hydrocarbons and do not contain any reactive groups that would interfere with Grignard reagents, making them suitable solvents.
Step 3: Evaluate ethers such as CH3-O-CH3 (b) and CH3OCH2CH2OCH3 (f). Ethers are commonly used solvents for Grignard reactions because they are aprotic and can stabilize the Grignard reagent through coordination with the magnesium atom.
Step 4: Examine compounds like CHCl3 (c) and benzene (e). CHCl3 contains acidic hydrogen atoms and is unsuitable for Grignard reactions. Benzene is non-polar and inert, making it a suitable solvent.
Step 5: Assess the cyclic ethers provided in the image, (vii) and (viii). Both are cyclic ethers, which are aprotic and can stabilize Grignard reagents through coordination. Therefore, they are suitable solvents for Grignard reactions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Grignard Reagents
Grignard reagents are organomagnesium compounds formed by the reaction of magnesium with alkyl or aryl halides. They are highly reactive and serve as nucleophiles in organic synthesis, particularly in forming carbon-carbon bonds. Understanding their reactivity is crucial for determining suitable solvents, as they can react with protic solvents, leading to the destruction of the Grignard reagent.
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Carbonation of Grignard Reagents
Solvent Properties
The choice of solvent in Grignard reactions is critical, as it must be an aprotic solvent that does not contain acidic protons. Suitable solvents, such as ethers, stabilize the Grignard reagent without participating in the reaction. Common examples include diethyl ether and tetrahydrofuran (THF), which provide a non-reactive environment for the reaction to proceed effectively.
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Reactivity of Solvents
Different solvents exhibit varying degrees of reactivity with Grignard reagents. For instance, solvents like water or alcohols can protonate Grignard reagents, rendering them ineffective. In contrast, hydrocarbons like n-hexane and cyclohexane are non-polar and do not react with Grignard reagents, making them unsuitable for facilitating the desired reactions. Understanding these interactions is essential for selecting appropriate solvents.
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Related Practice
Textbook Question
Predict the products of the following reactions.
(a)
(b)
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Textbook Question
For each molecular formula, draw all the possible constitutional isomers of alcohols with that formula. Give the IUPAC name for each alcohol.(a) C3H8O(b) C4H10O(c) C3H6O(d) C3H4O
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Textbook Question
Show how you would synthesize the following primary alcohol by adding an appropriate Grignard reagent to formaldehyde.
(a)
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Textbook Question
The following compounds are only slightly soluble in water, but one of them is very soluble in a dilute aqueous solution of sodium hydroxide. The other is still only slightly soluble.
(a) Explain the difference in solubility of these compounds in dilute sodium hydroxide.
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Textbook Question
The following compounds are only slightly soluble in water, but one of them is very soluble in a dilute aqueous solution of sodium hydroxide. The other is still only slightly soluble.
(b) Show how this difference might be exploited to separate a mixture of these two compounds using a separatory funnel.
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