Textbook Question
Draw the structures of the aldehydes that might be oxidized to yield the following carboxylic acids:
c. CH3CH=CHCOOH
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14. Compounds with Oxygen or Sulfur
Alcohol Reactions: Oxidation Reactions
Problem 32c
Textbook Question
Draw the condensed structural formulas for the aldehyde and carboxylic acid produced when each of the following is oxidized:
c. 3-chloro-1-propanol
Verified step by step guidance1
Step 1: Understand the oxidation process for alcohols. Primary alcohols, such as 3-chloro-1-propanol, are oxidized first to aldehydes and then further oxidized to carboxylic acids. This involves the removal of hydrogen atoms and the addition of oxygen atoms.
Step 2: Identify the structure of 3-chloro-1-propanol. The molecule consists of a three-carbon chain with a hydroxyl (-OH) group attached to the first carbon and a chlorine atom attached to the third carbon. Its condensed structural formula is CH2Cl-CH2-CH2OH.
Step 3: Determine the aldehyde produced in the first step of oxidation. The hydroxyl group (-OH) on the first carbon is oxidized to a carbonyl group (-CHO), forming an aldehyde. The condensed structural formula for the aldehyde is CH2Cl-CH2-CHO.
Step 4: Determine the carboxylic acid produced in the second step of oxidation. The aldehyde group (-CHO) is further oxidized to a carboxylic acid group (-COOH). The condensed structural formula for the carboxylic acid is CH2Cl-CH2-COOH.
Step 5: Summarize the oxidation process. The primary alcohol (3-chloro-1-propanol) is oxidized first to an aldehyde (CH2Cl-CH2-CHO) and then to a carboxylic acid (CH2Cl-CH2-COOH). These transformations involve the progressive addition of oxygen atoms to the functional group.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation Reactions
Oxidation reactions involve the loss of electrons or an increase in oxidation state by a molecule. In organic chemistry, this often refers to the conversion of alcohols to aldehydes or carboxylic acids. Understanding the mechanism of oxidation is crucial for predicting the products formed when specific alcohols, like 3-chloro-1-propanol, undergo oxidation.
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Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In this case, the aldehyde group (-CHO) and the carboxylic acid group (-COOH) are key functional groups that result from the oxidation of alcohols. Recognizing these groups helps in drawing the correct condensed structural formulas.
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Condensed Structural Formulas
Condensed structural formulas provide a simplified representation of a molecule's structure, showing the arrangement of atoms and functional groups without depicting all the bonds explicitly. For aldehydes and carboxylic acids, these formulas highlight the key functional groups and the carbon skeleton, making it easier to visualize the molecular structure resulting from the oxidation of 3-chloro-1-propanol.
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