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H Ph 1. HO A NaOH Ph Br DMSO / H20 2. N-Br ...HO. N-H a = Proton transfer d = Radical chain addition g = E2 Elimination b = Lewis acid/base e = Electrophilic addition h = SN1 Nucleophilic substitution %3D %3D c = Radical chain substitution f=E1 Elimination i = SN2 Nucleophilic substitution Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. 1. 2.

H Ph 1. HO A NaOH Ph Br DMSO / H20 2. N-Br ...HO. N-H a = Proton transfer d = Radical chain addition g = E2 Elimination b = Lewis acid/base e = Electrophilic addition h = SN1 Nucleophilic substitution %3D %3D c = Radical chain substitution f=E1 Elimination i = SN2 Nucleophilic substitution Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. 1. 2.

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
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### Chemical Reaction Mechanism Identification #### Reaction 1: **Reactants:** - A molecule with a phenyl group (-Ph), chlorine (-Cl), and a hydrogen substituted on a carbon, reacting with sodium hydroxide (NaOH). **Products:** - A phenyl group attached to a cyclopropenone. #### Reaction 2: **Reactants:** - A cyclohexanone reacting with an N-bromo compound in the presence of DMSO (Dimethyl sulfoxide) and water (H<sub>2</sub>O). **Products:** - A brominated cyclopentanone and an imidic product. **Mechanisms:** a) Proton transfer b) Lewis acid/base c) Radical chain substitution d) Radical chain addition e) Electrophilic addition f) E1 Elimination g) E2 Elimination h) S<sub>N1</sub> Nucleophilic substitution i) S<sub>N2</sub> Nucleophilic substitution #### Instructions: Identify the mechanism by which each of the reactions proceeds from among the mechanisms listed. Use the letters a - i for your answers. 1. **_____** 2. **_____** **Graph/Diagram Description:** - The diagrams consist of molecular structures of reactants and products. In reaction 1, there is a structural transformation from a phenyl-substituted molecule with a chlorine substituent to a phenylcyclopropenone. - In reaction 2, the reactants include a cyclohexanone and a brominated amide. The product formation includes a creation of a brominated cyclopentanone with an imidic compound. **Note:** Understanding and identifying the correct mechanism for each reaction is essential for grasping organic chemistry reaction pathways and the principles governing chemical reactivity and product formation.
Transcribed Image Text:### Chemical Reaction Mechanism Identification #### Reaction 1: **Reactants:** - A molecule with a phenyl group (-Ph), chlorine (-Cl), and a hydrogen substituted on a carbon, reacting with sodium hydroxide (NaOH). **Products:** - A phenyl group attached to a cyclopropenone. #### Reaction 2: **Reactants:** - A cyclohexanone reacting with an N-bromo compound in the presence of DMSO (Dimethyl sulfoxide) and water (H<sub>2</sub>O). **Products:** - A brominated cyclopentanone and an imidic product. **Mechanisms:** a) Proton transfer b) Lewis acid/base c) Radical chain substitution d) Radical chain addition e) Electrophilic addition f) E1 Elimination g) E2 Elimination h) S<sub>N1</sub> Nucleophilic substitution i) S<sub>N2</sub> Nucleophilic substitution #### Instructions: Identify the mechanism by which each of the reactions proceeds from among the mechanisms listed. Use the letters a - i for your answers. 1. **_____** 2. **_____** **Graph/Diagram Description:** - The diagrams consist of molecular structures of reactants and products. In reaction 1, there is a structural transformation from a phenyl-substituted molecule with a chlorine substituent to a phenylcyclopropenone. - In reaction 2, the reactants include a cyclohexanone and a brominated amide. The product formation includes a creation of a brominated cyclopentanone with an imidic compound. **Note:** Understanding and identifying the correct mechanism for each reaction is essential for grasping organic chemistry reaction pathways and the principles governing chemical reactivity and product formation.
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