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Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.

Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Question 6
**Predicting Products in Chemical Reactions: Indicating Regiochemistry and Stereochemistry** **Reaction: Addition of Chlorine Water to Styrene** In this reaction, styrene (phenylethylene) undergoes an addition reaction with chlorine water (Cl₂ and H₂O). **Reactants:** - Styrene (C₆H₅-CH=CH₂) - Chlorine Water (Cl₂ in H₂O) **Products:** - The major product of the reaction is 1-phenyl-1,2-dichloroethanol. **Mechanism:** 1. Electrophilic Attack: The double bond in styrene breaks and forms a chloronium ion intermediate. 2. Nucleophilic Attack: Water (H₂O) acts as the nucleophile, attacking the more substituted carbon. 3. Deprotonation: The molecule deprotonates to yield the final product. **Regiochemistry:** - The chlorine (Cl) will add to the less substituted carbon of the double bond (Markovnikov's rule), leading to the formation of an intermediate where the more stable carbocation forms at the benzylic (adjacent to the benzene ring) position. - Water attacks the carbocation, leading to the formation of an alcohol at the more substituted carbon (benzylic position). **Stereochemistry:** - This is not explicitly mentioned in simple reactions, but if the starting material was chiral or stereospecific products were expected, stereochemistry would need to be considered. Thus, the structure of 1-phenyl-1,2-dichloroethanol would be: C6H5-CHCl-CHCl-OH When predicting products in such reactions, it is crucial to consider both regiochemistry (the specific regions on a molecule where reactions occur) and stereochemistry (the spatial arrangement of atoms).
Transcribed Image Text:**Predicting Products in Chemical Reactions: Indicating Regiochemistry and Stereochemistry** **Reaction: Addition of Chlorine Water to Styrene** In this reaction, styrene (phenylethylene) undergoes an addition reaction with chlorine water (Cl₂ and H₂O). **Reactants:** - Styrene (C₆H₅-CH=CH₂) - Chlorine Water (Cl₂ in H₂O) **Products:** - The major product of the reaction is 1-phenyl-1,2-dichloroethanol. **Mechanism:** 1. Electrophilic Attack: The double bond in styrene breaks and forms a chloronium ion intermediate. 2. Nucleophilic Attack: Water (H₂O) acts as the nucleophile, attacking the more substituted carbon. 3. Deprotonation: The molecule deprotonates to yield the final product. **Regiochemistry:** - The chlorine (Cl) will add to the less substituted carbon of the double bond (Markovnikov's rule), leading to the formation of an intermediate where the more stable carbocation forms at the benzylic (adjacent to the benzene ring) position. - Water attacks the carbocation, leading to the formation of an alcohol at the more substituted carbon (benzylic position). **Stereochemistry:** - This is not explicitly mentioned in simple reactions, but if the starting material was chiral or stereospecific products were expected, stereochemistry would need to be considered. Thus, the structure of 1-phenyl-1,2-dichloroethanol would be: C6H5-CHCl-CHCl-OH When predicting products in such reactions, it is crucial to consider both regiochemistry (the specific regions on a molecule where reactions occur) and stereochemistry (the spatial arrangement of atoms).
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