Textbook Question
What is the major product(s) of each of the following reactions?
d.
2
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Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
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. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 63g
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 63gChapter 11, Problem 63g
What is the major product(s) of each of the following reactions?
g. 
Verified step by step guidance1
Step 1: Analyze the starting material. The molecule is a cyclopentanol derivative with a hydroxyl (-OH) group and a methyl group attached to the ring. The hydroxyl group is in the axial position.
Step 2: Understand the role of TsCl/pyridine. Tosyl chloride (TsCl) reacts with the hydroxyl group in the presence of pyridine to convert it into a tosylate (-OTs) group. This step makes the hydroxyl group a better leaving group.
Step 3: Consider the stereochemistry of the tosylation reaction. The tosylate group will retain the stereochemistry of the original hydroxyl group, as this reaction does not invert the configuration.
Step 4: Examine the second reagent, NaCN. Sodium cyanide (NaCN) is a nucleophile that will perform an SN2 reaction, displacing the tosylate group. Since SN2 reactions proceed with inversion of configuration, the cyanide group (-CN) will attach to the carbon in the equatorial position.
Step 5: Predict the major product. The major product will be a cyclopentane ring with a cyanide group (-CN) in the equatorial position and a methyl group in the axial position, due to the stereochemical inversion during the SN2 reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alcohol Activation
In organic chemistry, alcohols can be converted into better leaving groups through activation. In this reaction, TsCl (tosyl chloride) is used in the presence of pyridine to convert the alcohol (-OH) into a tosylate, which is a more reactive species. This transformation facilitates subsequent nucleophilic substitution reactions.
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Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, after the alcohol is converted to a tosylate, NaCN (sodium cyanide) acts as the nucleophile, attacking the carbon atom bonded to the tosylate and resulting in the formation of a nitrile (R-C≡N).
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Formation of Nitriles
Nitriles are organic compounds containing a cyano group (-C≡N) and are often formed through nucleophilic substitution reactions involving alkyl halides or activated alcohols. The reaction of the tosylate with NaCN leads to the formation of a nitrile, which can be useful in various synthetic applications, including the synthesis of amines and carboxylic acids.
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Related Practice
Textbook Question
What is the major product(s) of each of the following reactions?
a.
b.
2
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Textbook Question
What is the major product(s) of each of the following reactions?
h.
1
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Textbook Question
In Section 10.12, we saw that S-adenosylmethionine (SAM) methylates the nitrogen atom of noradrenaline to form adrenaline, a more potent hormone. If SAM methylates an OH group attached to the benzene ring instead, it completely destroys noradrenaline's activity.
b. Which reaction is more apt to occur, methylation on nitrogen or methylation on oxygen?
1
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Textbook Question
An unknown alcohol with a molecular formula of C7H14O was oxidized to an aldehyde with HOCl. When an acidic solution of the alcohol was distilled, two alkenes were obtained. The alkene formed in greater yield was determined to be 1-methylcyclohexene. The other alkene formed the original un-known alcohol when treated with BH3/THF followed by H2O2, HO-, and H2O. Identify the unknown alcohol.
9
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Textbook Question
What is the major product(s) of each of the following reactions?
c.
1
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