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12I Draw the product(s) of elimination and a complete mechanism (El or E2) for each reaction. Include possible rearrangement and circle the major product. CH3OH CH,CH,0 CH,OH a. b. Br C. CH,OH SN, CHS BrO CH, CH SN, HCH Br OCH3

12I Draw the product(s) of elimination and a complete mechanism (El or E2) for each reaction. Include possible rearrangement and circle the major product. CH3OH CH,CH,0 CH,OH a. b. Br C. CH,OH SN, CHS BrO CH, CH SN, HCH Br OCH3

Chemistry
Chemistry
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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
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**Exercise: Draw the products of elimination and a complete mechanism (E1 or E2) for each reaction. Include possible rearrangement and circle the major product.** ### Reaction Descriptions: #### Reaction a: - Initial molecule: Cyclohexane with Br substituent. - Mechanism: E2 - Reactants: Methanol (\(CH_3OH\)) - Step 1: Elimination of Br with the formation of a double bond. - Product: Cyclohexene. - Major Product: Cyclohexene (circled). #### Reaction b: - Initial molecule: 2-bromo-2-methylpentane. - Mechanism: Combination of E1 and SN1. - Reactants: Methanol (\(CH_3OH\)) - Step 1: Loss of Br to form a tertiary carbocation. - Step 2: Methanol attacks the carbocation, forming an ether. - Step 3: Elimination of the proton from methanol. - Rearrangement: Possible shifts leading to a more stabilized product. - Major products: - \(CH_3OH\) attachment (illustrating SN1). - Olefin (E1 reaction illustrated). #### Reaction c: - Initial molecule: 3-bromo-3-methylpentane. - Mechanism: E1 - Reactants: Methanol (\(CH_3OH\)) - Step 1: Loss of Br forms a stable carbocation. - Step 2: Formation of a double bond through elimination. - Product: Multiple possible alkene structures. - Major Product: The more substituted alkene resulting from the rearrangement (circled). Each reaction is carefully sketched, showing the movement of electrons and intermediates, with arrows indicating the changes and rearrangements. ### Diagram Explanations: - Arrows in the diagrams represent the flow of electrons during bond formation or breaking. - Each reaction pathway is labeled to indicate whether it follows an E1 or E2 elimination mechanism. - The major products in each category are circled to highlight the predominant outcome.
Transcribed Image Text:**Exercise: Draw the products of elimination and a complete mechanism (E1 or E2) for each reaction. Include possible rearrangement and circle the major product.** ### Reaction Descriptions: #### Reaction a: - Initial molecule: Cyclohexane with Br substituent. - Mechanism: E2 - Reactants: Methanol (\(CH_3OH\)) - Step 1: Elimination of Br with the formation of a double bond. - Product: Cyclohexene. - Major Product: Cyclohexene (circled). #### Reaction b: - Initial molecule: 2-bromo-2-methylpentane. - Mechanism: Combination of E1 and SN1. - Reactants: Methanol (\(CH_3OH\)) - Step 1: Loss of Br to form a tertiary carbocation. - Step 2: Methanol attacks the carbocation, forming an ether. - Step 3: Elimination of the proton from methanol. - Rearrangement: Possible shifts leading to a more stabilized product. - Major products: - \(CH_3OH\) attachment (illustrating SN1). - Olefin (E1 reaction illustrated). #### Reaction c: - Initial molecule: 3-bromo-3-methylpentane. - Mechanism: E1 - Reactants: Methanol (\(CH_3OH\)) - Step 1: Loss of Br forms a stable carbocation. - Step 2: Formation of a double bond through elimination. - Product: Multiple possible alkene structures. - Major Product: The more substituted alkene resulting from the rearrangement (circled). Each reaction is carefully sketched, showing the movement of electrons and intermediates, with arrows indicating the changes and rearrangements. ### Diagram Explanations: - Arrows in the diagrams represent the flow of electrons during bond formation or breaking. - Each reaction pathway is labeled to indicate whether it follows an E1 or E2 elimination mechanism. - The major products in each category are circled to highlight the predominant outcome.
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