Textbook Question
How could each of the following compounds be prepared from cyclohexanone?
a.
1
views
Ch. 17 - Reactions at the Alpha-Carbon
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
Chapter 18, Problem 14a
How could each of the following compounds be prepared from a ketone and an alkyl halide?
a. 
Verified step by step guidance1
Step 1: Identify the target compound. The structure provided is a ketone with an alkyl group containing a double bond attached to the alpha-carbon. This suggests the use of an alkylation reaction.
Step 2: Select the starting ketone. The ketone in the target compound is cyclopentanone, which will serve as the starting material.
Step 3: Choose the alkyl halide. The alkyl group attached to the alpha-carbon contains a double bond, indicating that the alkyl halide should be allyl bromide (CH2=CH-CH2Br).
Step 4: Use a base to generate the enolate ion from the ketone. A strong base such as sodium hydride (NaH) or LDA (Lithium Diisopropylamide) can be used to deprotonate the alpha-carbon of cyclopentanone, forming the enolate ion.
Step 5: Perform the alkylation reaction. React the enolate ion with allyl bromide in an SN2 reaction to attach the allyl group to the alpha-carbon of cyclopentanone, forming the target compound.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Enolate Formation
Enolates are nucleophilic species formed from the deprotonation of a carbonyl compound, such as a ketone. This process typically involves a strong base that abstracts an alpha-hydrogen, resulting in a resonance-stabilized anion. Enolates are crucial intermediates in organic synthesis, particularly in reactions like alkylation, where they can react with alkyl halides to form new carbon-carbon bonds.
Recommended video:
Guided course
02:26
Formation of Enolates
Alkylation of Enolates
Alkylation of enolates involves the reaction of an enolate ion with an alkyl halide to form a new carbon-carbon bond. This reaction is typically carried out under conditions that favor the formation of the enolate, followed by the nucleophilic attack on the electrophilic carbon of the alkyl halide. The choice of alkyl halide can influence the regioselectivity and stereochemistry of the resulting product.
Recommended video:
Guided course
03:05Enolates of Esters
Synthesis of Carbonyl Compounds
The synthesis of carbonyl compounds from ketones and alkyl halides often involves multiple steps, including enolate formation and subsequent alkylation. This strategy allows for the construction of complex molecules by introducing new alkyl groups at specific positions. Understanding the reactivity of both the ketone and the alkyl halide is essential for predicting the outcome of the synthesis and for optimizing reaction conditions.
Recommended video:
Guided course
01:40Defining meso compounds.
Related Practice
Textbook Question
Show how the following compounds can be prepared from the given starting material:
a.
1
views
Textbook Question
Draw the enol tautomers for each of the following compounds. For compounds that have more than one enol tautomer, indicate the one that is more stable.
f.
1
views
Textbook Question
A ketone undergoes acid-catalyzed bromination, acid-catalyzed chlorination, racemization, and acid-catalyzed deuterium exchange at the ⍺-carbon. All of these reactions have similar rate constants.What does this tell you about the mechanisms of these reactions?
2
views
Textbook Question
How could each of the following compounds be prepared from a ketone and an alkyl halide?
b.
4
views
Textbook Question
How could each of the following compounds be prepared from cyclohexanone?
b.
1
views