Textbook Question
Predict the major products of the following reactions.
f. 1-ethylcycloheptene + cold, dilute KMnO4
10. Addition Reactions
Dihydroxylation
Problem 49f
Textbook Question
Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.
(f) 
Verified step by step guidance1
Step 1: Begin by identifying the target molecule, which is a 1,2-diol (two hydroxyl groups on adjacent carbons) with a total of 8 carbons in the chain. The synthesis must start with organic molecules containing three carbons or fewer.
Step 2: To construct the carbon chain, use successive alkylation reactions. Start with a three-carbon molecule such as propanal or propanone. Perform aldol condensation reactions to elongate the chain step by step, ensuring the correct connectivity of carbons.
Step 3: Once the desired carbon chain length is achieved (8 carbons), introduce the hydroxyl groups. Use epoxidation of an alkene intermediate followed by acid-catalyzed ring opening to form the 1,2-diol. For example, convert the terminal alkene to an epoxide using a peracid (e.g., mCPBA), then hydrolyze the epoxide under acidic conditions.
Step 4: Ensure stereochemistry is correct. If the target molecule requires specific stereochemistry, use reagents or conditions that favor the desired stereochemical outcome during the epoxide ring opening.
Step 5: Purify the final product using techniques such as distillation or recrystallization, and confirm the structure using spectroscopic methods like NMR and IR to ensure the synthesis was successful.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic chemistry, common functional groups include alcohols (–OH), carboxylic acids (–COOH), and amines (–NH2). Understanding functional groups is essential for predicting the reactivity and properties of organic compounds.
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Synthesis of Organic Molecules
The synthesis of organic molecules involves constructing complex molecules from simpler ones through various chemical reactions. This process often requires knowledge of reaction mechanisms, reagents, and conditions. In this context, starting with molecules containing three carbons or fewer means utilizing basic building blocks like propane, propene, or alcohols to create larger, more complex structures.
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Carbon Chain Length and Structure
The length and structure of carbon chains significantly influence the properties and reactivity of organic molecules. In the provided image, the molecule features a longer carbon chain with hydroxyl (–OH) groups, indicating it is likely a polyol. Understanding how to manipulate carbon chain length and branching is crucial for synthesizing desired organic compounds and predicting their behavior in reactions.
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