교과서 질문
Show how Friedel–Crafts acylation might be used to synthesize the following compounds.
c. n-butylbenzene
681
views
Ch. 21 - Carboxylic Acid Derivatives
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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TOC.tableOfContents
- 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
21장, 문제 32a,b
Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.
(a) n-octyl formate
(b) n-octyl acetate
검증된 단계별 안내1
Step 1: Understand the structure of the target compounds. (a) n-octyl formate is an ester with the formula CH3(CH2)6CH2OCHO, where the alcohol component is n-octanol and the acid component is formic acid. (b) n-octyl acetate is an ester with the formula CH3(CH2)6CH2OCOCH3, where the alcohol component is n-octanol and the acid component is acetic acid.
Step 2: Recall the general reaction mechanism for ester synthesis using anhydrides. Anhydrides react with alcohols to form esters and a carboxylic acid byproduct. This reaction is typically preferred over using acid chlorides because anhydrides are less reactive, easier to handle, and do not produce corrosive HCl as a byproduct.
Step 3: For (a) n-octyl formate, use formic anhydride (HCO)2O as the starting anhydride. React n-octanol (CH3(CH2)6CH2OH) with formic anhydride. The reaction proceeds via nucleophilic attack of the alcohol oxygen on the carbonyl carbon of the anhydride, followed by elimination of formic acid (HCOOH) as the byproduct.
Step 4: For (b) n-octyl acetate, use acetic anhydride (CH3CO)2O as the starting anhydride. React n-octanol (CH3(CH2)6CH2OH) with acetic anhydride. The reaction mechanism is similar to (a), where the alcohol oxygen attacks the carbonyl carbon of the anhydride, leading to the formation of n-octyl acetate and acetic acid (CH3COOH) as the byproduct.
Step 5: Summarize why anhydrides are preferable to acid chlorides. Anhydrides are less reactive than acid chlorides, making them easier to control in reactions. They do not produce corrosive HCl, which can be problematic in certain reaction setups. Additionally, the byproducts (formic acid or acetic acid) are less hazardous and easier to handle compared to HCl.
비슷한 문제에 대한 검증된 영상 답변:
이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
6m주요 개념
질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.
Anhydrides in Organic Synthesis
Anhydrides are reactive compounds derived from acids by the removal of water. They are commonly used in organic synthesis due to their ability to acylate nucleophiles, forming esters or amides. Their reactivity allows for the formation of carbon-carbon bonds, making them versatile intermediates in the synthesis of various organic compounds.
추천 영상:
03:35
Anhydride Nomenclature
Comparison of Anhydrides and Acid Chlorides
While both anhydrides and acid chlorides are acylating agents, anhydrides are often preferred due to their milder reactivity and lower toxicity. Acid chlorides can be more reactive, leading to side reactions or decomposition, whereas anhydrides can provide better control over the reaction conditions, resulting in higher yields of the desired product.
추천 영상:
03:13Acid Chloride Nomenclature
Synthesis of Esters
The synthesis of esters from alcohols and acylating agents like anhydrides involves a nucleophilic acyl substitution mechanism. In this process, the alcohol acts as a nucleophile, attacking the carbonyl carbon of the anhydride, leading to the formation of the ester and a carboxylic acid. Understanding this mechanism is crucial for predicting the outcomes of the reactions in the given synthesis tasks.
추천 영상:
가이드 코스
01:28Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis Example 2
관련 실천
교과서 질문
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(b)
683
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교과서 질문
Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.
(c) phthalic acid monoamide
(d) succinic acid monomethyl ester
597
views
교과서 질문
Show how Friedel–Crafts acylation might be used to synthesize the following compounds.
a. acetophenone
1313
views
교과서 질문
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(a)
860
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교과서 질문
Show how Friedel–Crafts acylation might be used to synthesize the following compounds.
b. benzophenone
1027
views