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diastereomers. II

diastereomers. II

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter12: Chirality
Section: Chapter Questions
Problem 6E
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**Instructions for Classifying Molecules** **Objective:** Classify the following pairs of molecules as identical, constitutional isomers, enantiomers, or diastereomers. **Pairs of Molecules:** 1. **Top Left Pair:** - The first molecule (left): A cyclohexane ring with a methyl group and an ethyl group attached, both substituents represented in wedge (outward) and dashed (inward) bond configurations. - The second molecule (right): Similar cyclohexane structure with a methyl group and an ethyl group, but on different carbons or with different configurations. 2. **Second Row Pair:** - The first molecule (left): A straight-chain alkane with two chiral centers, substituents along the chain have different stereochemistry (wedge and dash represent different stereo orientations). - The second molecule (right): Similar chain with identical substituents but different stereochemistry compared to the first molecule. 3. **Third Row Pair:** - The first molecule (left): A molecule with a chlorine (Cl) and bromine (Br) substituent on a two-carbon chain, both showing different stereochemical orientations. - The second molecule (right): Similar two-carbon structure, with both substituents (Cl and Br) presenting different stereochemistry compared to the first molecule. 4. **Bottom Pair:** - The first molecule (left): A three-carbon alkane with substituents showing specific stereochemistry. - The second molecule (right): The same three-carbon structure, but with stereochemistry exactly inverted or different from the first. **Explanation:** In order to classify these molecules: - **Identical molecules** have the same connectivity and the same stereochemistry. - **Constitutional isomers** have the same molecular formula but different connectivity. - **Enantiomers** are non-superimposable mirror images, having stereocenters with all opposite configurations. - **Diastereomers** have the same connectivity but are not mirror images, with some differing stereocenters. Carefully analyze connectivity and stereo orientation using the standard notations (wedges and dashes) to determine the type of isomerism or identity for each pair.
Transcribed Image Text:**Instructions for Classifying Molecules** **Objective:** Classify the following pairs of molecules as identical, constitutional isomers, enantiomers, or diastereomers. **Pairs of Molecules:** 1. **Top Left Pair:** - The first molecule (left): A cyclohexane ring with a methyl group and an ethyl group attached, both substituents represented in wedge (outward) and dashed (inward) bond configurations. - The second molecule (right): Similar cyclohexane structure with a methyl group and an ethyl group, but on different carbons or with different configurations. 2. **Second Row Pair:** - The first molecule (left): A straight-chain alkane with two chiral centers, substituents along the chain have different stereochemistry (wedge and dash represent different stereo orientations). - The second molecule (right): Similar chain with identical substituents but different stereochemistry compared to the first molecule. 3. **Third Row Pair:** - The first molecule (left): A molecule with a chlorine (Cl) and bromine (Br) substituent on a two-carbon chain, both showing different stereochemical orientations. - The second molecule (right): Similar two-carbon structure, with both substituents (Cl and Br) presenting different stereochemistry compared to the first molecule. 4. **Bottom Pair:** - The first molecule (left): A three-carbon alkane with substituents showing specific stereochemistry. - The second molecule (right): The same three-carbon structure, but with stereochemistry exactly inverted or different from the first. **Explanation:** In order to classify these molecules: - **Identical molecules** have the same connectivity and the same stereochemistry. - **Constitutional isomers** have the same molecular formula but different connectivity. - **Enantiomers** are non-superimposable mirror images, having stereocenters with all opposite configurations. - **Diastereomers** have the same connectivity but are not mirror images, with some differing stereocenters. Carefully analyze connectivity and stereo orientation using the standard notations (wedges and dashes) to determine the type of isomerism or identity for each pair.
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