Textbook Question
Predict the products of the following reactions.
(k)
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Ch. 21 - Carboxylic Acid Derivatives
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 21, Problem 50l
Predict the products of the following reactions.
(l) 
Verified step by step guidance1
Step 1: Identify the functional groups in the reactants. The cyclic compound contains a ketone and an ester functional group. The second reactant is ethylene glycol (HOCH₂CH₂OH), which is a diol (contains two hydroxyl groups). The reaction occurs under acidic conditions (H⁺).
Step 2: Recognize the type of reaction. This is an acetal formation reaction, where a ketone reacts with a diol under acidic conditions to form a cyclic acetal. Acetals are stable compounds often used to protect carbonyl groups in organic synthesis.
Step 3: Understand the mechanism. The reaction begins with protonation of the ketone oxygen by the acid catalyst, making the carbonyl carbon more electrophilic. The diol then attacks the carbonyl carbon, forming a tetrahedral intermediate.
Step 4: The intermediate undergoes proton transfer and elimination of water to form a hemiacetal. The second hydroxyl group of the diol then attacks the hemiacetal carbon, leading to the formation of a cyclic acetal after another elimination of water.
Step 5: Predict the product. The cyclic acetal formed will have the diol incorporated into the structure, with the two oxygen atoms of the diol forming a ring with the original carbonyl carbon. This protects the ketone group in the molecule.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Catalyzed Reactions
Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction. In organic chemistry, acids can protonate reactants, making them more electrophilic and facilitating nucleophilic attacks. This is particularly important in reactions involving alcohols and carbonyl compounds, where the acid can enhance the reactivity of the carbonyl carbon.
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Acid Catalyzed
Nucleophilic Addition
Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically found in carbonyl groups. In this case, the alcohol acts as a nucleophile, attacking the electrophilic carbon of the cyclic compound's carbonyl, leading to the formation of a new bond and the potential for product formation.
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Cyclic Compounds and Ring Strain
Cyclic compounds are molecules that contain a ring structure, which can introduce ring strain depending on the size and substituents of the ring. In the context of the reaction, the cyclic compound may have specific steric and electronic properties that influence its reactivity with the alcohol. Understanding the stability and strain of the ring is crucial for predicting the outcome of the reaction.
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Related Practice
Textbook Question
Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.
(b) Predict the products formed when phosgene reacts with 1 equivalent of methanol, followed by 1 equivalent of aniline.
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Textbook Question
Predict the products of the following reactions.
(j)
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Textbook Question
Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.
(a) Predict the products formed when phosgene reacts with excess propan-2-ol.
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Textbook Question
Predict the products of the following reactions.
(i)
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Textbook Question
An ether extraction of nutmeg gives large quantities of trimyristin, a waxy crystalline solid of melting point 57°C. The IR spectrum of trimyristin shows a very strong absorption at 1733 cm-1. Basic hydrolysis of trimyristin gives 1 equivalent of glycerol and 3 equivalents of myristic acid (tetradecanoic acid).
(a) Draw the structure of trimyristin.
(b) Predict the products formed when trimyristin is treated with lithium aluminum hydride, followed by aqueous hydrolysis of the aluminum salts.
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