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 51a
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.
Verified step by step guidance1
Step 1: Recognize the structure of phosgene (Cl2C=O), which is an acid chloride derived from carbonic acid. Acid chlorides are reactive electrophiles that undergo nucleophilic acyl substitution reactions.
Step 2: Identify the nucleophile in the reaction. In this case, excess propan-2-ol (CH3CHOHCH3) acts as the nucleophile. Alcohols are good nucleophiles due to the lone pairs on the oxygen atom.
Step 3: Predict the first reaction step. The nucleophilic oxygen of propan-2-ol attacks the carbonyl carbon of phosgene, displacing one chloride ion (Cl-) and forming an intermediate ester-like compound: CH3CHOHCH3-C(=O)-Cl.
Step 4: Predict the second reaction step. Since phosgene can react twice, another molecule of propan-2-ol attacks the remaining carbonyl chloride group in the intermediate, displacing the second chloride ion (Cl-) and forming the final product: CH3CHOHCH3-C(=O)-OCH3CHOHCH3.
Step 5: Summarize the reaction. The final products are a diester (formed by two molecules of propan-2-ol reacting with phosgene) and two chloride ions (Cl-) as byproducts.
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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 an acyl compound, leading to the replacement of a leaving group. In the case of phosgene, the nucleophile (propan-2-ol) attacks the carbonyl carbon, resulting in the formation of a tetrahedral intermediate that eventually collapses to yield a carboxylic acid derivative and release the leaving group.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Acid Chlorides
Acid chlorides are a class of reactive organic compounds characterized by the presence of a carbonyl group (C=O) bonded to a chlorine atom. They are highly reactive due to the electronegative chlorine, which makes the carbonyl carbon more susceptible to nucleophilic attack. Phosgene, as an acid chloride of carbonic acid, exhibits similar reactivity, allowing it to participate in nucleophilic acyl substitution reactions.
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Reactivity of Phosgene
Phosgene is notable for its ability to react twice with nucleophiles due to its two reactive acyl chloride groups. This property allows it to form products with two nucleophiles, such as propan-2-ol, leading to the generation of a diester. Understanding this reactivity is crucial for predicting the products of reactions involving phosgene and other similar acid chlorides.
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Related Practice
Textbook Question
Two widely used pain relievers are aspirin and acetaminophen. Show how you would synthesize these drugs from phenol.
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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.
(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)
754
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Textbook Question
Predict the products of the following reactions.
(l)
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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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