Phenacetin (shown in the margin) was once used in headache remedies but is now banned because of its potential for causing kidney damage. (a) Identify all the functional groups present in phenacetin. (b) Draw the structures of the carboxylic acid and amine needed to prepare phenacetin.
Ch.17 Carboxylic Acids and Their Derivatives
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187당신이 사용하는 게 아니라요?교과서 변경
17장, 문제 23a
Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.
a. Isopropyl benzoate
검증된 단계별 안내1
Identify the functional group in the compound. Isopropyl benzoate is an ester, which has the general structure RCOOR'. In this case, the R group is a benzene ring (benzoate), and the R' group is an isopropyl group.
Understand the reaction type. Acid-catalyzed hydrolysis of an ester involves breaking the ester bond in the presence of water and an acid catalyst, such as HCl or H2SO4. This reaction produces a carboxylic acid and an alcohol.
Write the general reaction for ester hydrolysis: . Here, the ester breaks into a carboxylic acid (RCOOH) and an alcohol (R'OH).
Apply the reaction to isopropyl benzoate. The ester bond between the benzene ring (R group) and the isopropyl group (R' group) will break. The benzene ring will form benzoic acid (), and the isopropyl group will form isopropanol ().
Draw the products. The products of the reaction are benzoic acid and isopropanol. Represent benzoic acid with a benzene ring attached to a carboxylic acid group (-COOH) and isopropanol as a three-carbon chain with a hydroxyl group (-OH) on the middle carbon.

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이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
주요 개념
질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.
Acid-Catalyzed Hydrolysis
Acid-catalyzed hydrolysis is a chemical reaction where an ester reacts with water in the presence of an acid catalyst, typically a strong acid like sulfuric acid. This process breaks the ester bond, resulting in the formation of an alcohol and a carboxylic acid. The acid catalyst increases the reaction rate by protonating the carbonyl oxygen, making the carbon more electrophilic and susceptible to nucleophilic attack by water.
추천 영상:
가이드 코스
Acid-Catalyzed Ester Hydrolysis Concept 1
Esters
Esters are organic compounds formed from the reaction of an alcohol and a carboxylic acid, characterized by the functional group -COO-. They often have distinctive fruity odors and are commonly found in natural and synthetic substances. In the context of hydrolysis, esters can be converted back into their parent alcohol and carboxylic acid through the addition of water, facilitated by an acid catalyst.
추천 영상:
가이드 코스
Common Naming: Esters Concept 2
Products of Hydrolysis
The products of acid-catalyzed hydrolysis of an ester include an alcohol and a carboxylic acid. For isopropyl benzoate, the hydrolysis would yield isopropanol (the alcohol) and benzoic acid (the carboxylic acid). Understanding the structure of the starting ester is crucial for predicting the specific products formed during the hydrolysis reaction.
추천 영상:
가이드 코스
Basic Hydrolysis Example 2
관련 실천
교과서 질문
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Draw structures of the amides that can be made from the following reactants:
a. CH3NH2 + (CH3)2CHCOOH →?
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교과서 질문
What carboxylic acids and amines result from hydrolysis of the following amides?
b. N,N-Dimethyl-p-nitrobenzamide
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교과서 질문
Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.
b.
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What carboxylic acids and amines result from hydrolysis of the following amides?
a.
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교과서 질문
Draw structures of the amides that can be made from the following reactants:
b.
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