Textbook Question
Using the pKa values listed in [TABLE 15.1], predict the products of the following reactions:
d.
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Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
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. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 12c
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 12cChapter 16, Problem 12c
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
c. 
Verified step by step guidance1
Step 1: Analyze the target compound structure. The compound shown is an ester with the formula CH3CH2C(O)OCH2CH2CH3. This indicates that the acetyl group (CH3CH2C(O)) is bonded to an ethoxy group (OCH2CH2CH3).
Step 2: Recall the general reaction for synthesizing esters from acyl chlorides. Acyl chlorides react with alcohols in the presence of a base or under neutral conditions to form esters.
Step 3: Identify the alcohol needed to form the ethoxy group in the ester. The ethoxy group (OCH2CH2CH3) comes from ethanol (CH3CH2OH), which acts as the neutral nucleophile in this reaction.
Step 4: Write the reaction mechanism. Acetyl chloride (CH3CH2COCl) reacts with ethanol (CH3CH2OH). The nucleophilic oxygen in ethanol attacks the carbonyl carbon of acetyl chloride, displacing the chloride ion and forming the ester.
Step 5: Ensure reaction conditions are suitable. This reaction typically occurs under neutral or slightly basic conditions to facilitate the nucleophilic attack and stabilize the intermediate formed during the reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the carbonyl carbon of a carboxylic acid derivative, leading to the replacement of a leaving group. This reaction is crucial for synthesizing various compounds, as it allows for the transformation of one functional group into another while maintaining the carbon skeleton.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Acetyl Chloride as an Acyl Chloride
Acetyl chloride is an acyl chloride that serves as a reactive electrophile in nucleophilic acyl substitution reactions. Its structure, featuring a carbonyl group adjacent to a chlorine atom, makes it highly susceptible to nucleophilic attack, facilitating the formation of carboxylic acid derivatives. Understanding its reactivity is essential for predicting the outcome of reactions involving acetyl chloride.
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Neutral Nucleophiles
Neutral nucleophiles are species that possess a lone pair of electrons but do not carry a formal charge. Common examples include alcohols and amines. In the context of nucleophilic acyl substitution, using a neutral nucleophile is important as it can effectively attack the electrophilic carbonyl carbon without introducing additional charges that could complicate the reaction mechanism.
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Related Practice
Textbook Question
What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following? b. a weaker base than the substituent that is attached to the acyl group
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Textbook Question
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
e.
1147
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Textbook Question
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
f.
1150
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Textbook Question
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
d.
1050
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Textbook Question
Using the pKa values listed in [TABLE 15.1], predict the products of the following reactions:
c.
1356
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