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H3C 1₂0 CH3 CH3 H H3CO+ H₂C CH3 Br₂ CH3OH n Br raw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions ^@C↔X ™ H3C OCH 3 CH3 H3C Br CH3 H3CO H3C CH3 Br CH3 H30

H3C 1₂0 CH3 CH3 H H3CO+ H₂C CH3 Br₂ CH3OH n Br raw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions ^@C↔X ™ H3C OCH 3 CH3 H3C Br CH3 H3CO H3C CH3 Br CH3 H30

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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The image displays a multi-step chemical reaction mechanism involving organic compounds. 1. **Reaction Overview:** - **Starting Material:** A branched alkane with the formula \( C_5H_{10} \), specifically 2-bromo-2-methylbutane. - **Reagents:** The reaction involves bromine (\( Br_2 \)) in methanol (\( CH_3OH \)). - **Product Formation:** The product is a brominated ether, where methanol performs a substitution reaction. 2. **Mechanism Step Detail:** - The reaction undergoes through a carbocation intermediate. - The first step shows the interaction of methanol with the carbocation, leading to the formation of an ether and the release of a proton. 3. **Arrow-Pushing Instructions:** - A blue button labeled "Arrow-pushing Instructions" is present, suggesting interactive learning content for understanding electron movement in reaction mechanisms. - Curved arrows in the mechanism diagrams indicate electron flow, demonstrating how nucleophiles attack the electrophile and how leaving groups depart. 4. **Diagrams:** - **Left Diagram:** The initial carbocation with methanol and water molecules. The oxygen in methanol has a lone pair. - **Right Diagram:** The resulting product is an ether with a hydronium ion (\( H_3O^+ \)), indicating proton transfer. This image is intended for educational purposes to explain reaction mechanisms and electron flow using curved arrow notation.
Transcribed Image Text:The image displays a multi-step chemical reaction mechanism involving organic compounds. 1. **Reaction Overview:** - **Starting Material:** A branched alkane with the formula \( C_5H_{10} \), specifically 2-bromo-2-methylbutane. - **Reagents:** The reaction involves bromine (\( Br_2 \)) in methanol (\( CH_3OH \)). - **Product Formation:** The product is a brominated ether, where methanol performs a substitution reaction. 2. **Mechanism Step Detail:** - The reaction undergoes through a carbocation intermediate. - The first step shows the interaction of methanol with the carbocation, leading to the formation of an ether and the release of a proton. 3. **Arrow-Pushing Instructions:** - A blue button labeled "Arrow-pushing Instructions" is present, suggesting interactive learning content for understanding electron movement in reaction mechanisms. - Curved arrows in the mechanism diagrams indicate electron flow, demonstrating how nucleophiles attack the electrophile and how leaving groups depart. 4. **Diagrams:** - **Left Diagram:** The initial carbocation with methanol and water molecules. The oxygen in methanol has a lone pair. - **Right Diagram:** The resulting product is an ether with a hydronium ion (\( H_3O^+ \)), indicating proton transfer. This image is intended for educational purposes to explain reaction mechanisms and electron flow using curved arrow notation.
### Transcription for Educational Website #### Organic Reaction Mechanism: Bromination in Aqueous Solution The image depicts a mechanism involving the reaction of an alkene with bromine (\( \text{Br}_2 \)) in water. The reaction involves the formation of a bromohydrin. --- #### Reaction Overview: 1. **Starting Materials:** - **Alkene**: A hydrocarbon featuring a double bond and an arrangement of carbon atoms with attached methyl groups. - \( \text{Br}_2 \), in the presence of water (\( \text{H}_2\text{O} \)). 2. **Product:** - **Bromohydrin**: A molecule featuring both a bromine atom and a hydroxyl group (\(-\text{OH}\)) bonded to adjacent carbon atoms. --- #### Mechanistic Steps: 1. **Formation of a Bromonium Ion:** - The alkene reacts with \( \text{Br}_2 \), leading to the formation of a bromonium ion intermediate. This structure has a three-membered ring with a positively charged bromine attached to the two carbons from the former double bond. 2. **Nucleophilic Attack by Water:** - **Transition Structure:** The positively charged bromonium ion is attacked by a water molecule, where the lone pair of the oxygen forms a bond with one of the carbons, opening the bromonium ring. - **Arrow Notation:** Curved arrows are drawn to indicate the flow of electrons in this nucleophilic attack step. 3. **Final Product:** - The opening of the ring and subsequent proton transfers result in the formation of the bromohydrin. The structure shows a hydroxyl group on one carbon and a bromine atom on the adjacent carbon, and a water molecule bonded to another carbon with a positive charge due to protonation. --- This reaction is an example of halohydrin formation, showcasing how alkenes can be functionalized to add both a halogen and hydroxyl group in positions that are vicinal, or neighboring.
Transcribed Image Text:### Transcription for Educational Website #### Organic Reaction Mechanism: Bromination in Aqueous Solution The image depicts a mechanism involving the reaction of an alkene with bromine (\( \text{Br}_2 \)) in water. The reaction involves the formation of a bromohydrin. --- #### Reaction Overview: 1. **Starting Materials:** - **Alkene**: A hydrocarbon featuring a double bond and an arrangement of carbon atoms with attached methyl groups. - \( \text{Br}_2 \), in the presence of water (\( \text{H}_2\text{O} \)). 2. **Product:** - **Bromohydrin**: A molecule featuring both a bromine atom and a hydroxyl group (\(-\text{OH}\)) bonded to adjacent carbon atoms. --- #### Mechanistic Steps: 1. **Formation of a Bromonium Ion:** - The alkene reacts with \( \text{Br}_2 \), leading to the formation of a bromonium ion intermediate. This structure has a three-membered ring with a positively charged bromine attached to the two carbons from the former double bond. 2. **Nucleophilic Attack by Water:** - **Transition Structure:** The positively charged bromonium ion is attacked by a water molecule, where the lone pair of the oxygen forms a bond with one of the carbons, opening the bromonium ring. - **Arrow Notation:** Curved arrows are drawn to indicate the flow of electrons in this nucleophilic attack step. 3. **Final Product:** - The opening of the ring and subsequent proton transfers result in the formation of the bromohydrin. The structure shows a hydroxyl group on one carbon and a bromine atom on the adjacent carbon, and a water molecule bonded to another carbon with a positive charge due to protonation. --- This reaction is an example of halohydrin formation, showcasing how alkenes can be functionalized to add both a halogen and hydroxyl group in positions that are vicinal, or neighboring.
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