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OH₂ Br 2. CO₂H Br₂ a = Proton transfer h = SN1 Nucleophilic substitution e = Electrophilic addition f = E1 Elimination b = Lewis acid/base i = SN2 Nucleophilic substitution c = Radical chain substitution g = E2 Elimination j = Electrophilic aromatic substitution d = Radical chain addition Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers. 1. 2. 1. OH HBr

OH₂ Br 2. CO₂H Br₂ a = Proton transfer h = SN1 Nucleophilic substitution e = Electrophilic addition f = E1 Elimination b = Lewis acid/base i = SN2 Nucleophilic substitution c = Radical chain substitution g = E2 Elimination j = Electrophilic aromatic substitution d = Radical chain addition Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers. 1. 2. 1. OH HBr

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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### Understanding Reaction Mechanisms in Organic Chemistry #### Reaction Mechanisms In organic chemistry, different types of reaction mechanisms describe how a chemical reaction proceeds from reactants to products. Each mechanism involves a series of steps describing the breaking and forming of bonds. Below are two example reactions, and you'll be asked to identify the mechanism used in each. #### Example Reactions **Reaction 1:** This reaction involves a cyclohexanol reacting with hydrobromic acid (HBr). The product of the reaction is a cyclohexyl carbocation and a bromide anion. **Reaction 2:** This reaction involves the addition of bromine (Br2) to an alkene, resulting in a dibrominated product. The reactant is a compound with a phenyl group (Ph-) and a carboxylic acid group (-CO2H), while the product is a vicinal dibromide with the substituents added on adjacent carbon atoms in the cyclohexane ring. #### Possible Mechanisms - **a. Proton transfer**: Movement of a proton from one molecule to another. - **b. Lewis acid/base**: Involving the interaction between a Lewis acid and a Lewis base. - **c. Radical chain substitution**: A substitution reaction involving radicals. - **d. Radical chain addition**: Addition reactions involving radicals. - **e. Electrophilic addition**: Addition of an electrophile to a nucleophile. - **f. E1 Elimination**: Unimolecular elimination mechanism. - **g. E2 Elimination**: Bimolecular elimination mechanism. - **h. S_N1 Nucleophilic substitution**: Unimolecular nucleophilic substitution. - **i. S_N2 Nucleophilic substitution**: Bimolecular nucleophilic substitution. - **j. Electrophilic aromatic substitution**: Substitution on an aromatic ring via an electrophile. #### Exercise Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers. 1. ______________ 2. ______________ **Explanation of Diagrams:** - **Diagram 1**: Shows an alcohol group (-OH) on cyclohexane reacting with HBr, resulting in a carbocation and a bromide ion. - **Diagram 2**: Illustrates an alkene with a phenyl group reacting with brom
Transcribed Image Text:### Understanding Reaction Mechanisms in Organic Chemistry #### Reaction Mechanisms In organic chemistry, different types of reaction mechanisms describe how a chemical reaction proceeds from reactants to products. Each mechanism involves a series of steps describing the breaking and forming of bonds. Below are two example reactions, and you'll be asked to identify the mechanism used in each. #### Example Reactions **Reaction 1:** This reaction involves a cyclohexanol reacting with hydrobromic acid (HBr). The product of the reaction is a cyclohexyl carbocation and a bromide anion. **Reaction 2:** This reaction involves the addition of bromine (Br2) to an alkene, resulting in a dibrominated product. The reactant is a compound with a phenyl group (Ph-) and a carboxylic acid group (-CO2H), while the product is a vicinal dibromide with the substituents added on adjacent carbon atoms in the cyclohexane ring. #### Possible Mechanisms - **a. Proton transfer**: Movement of a proton from one molecule to another. - **b. Lewis acid/base**: Involving the interaction between a Lewis acid and a Lewis base. - **c. Radical chain substitution**: A substitution reaction involving radicals. - **d. Radical chain addition**: Addition reactions involving radicals. - **e. Electrophilic addition**: Addition of an electrophile to a nucleophile. - **f. E1 Elimination**: Unimolecular elimination mechanism. - **g. E2 Elimination**: Bimolecular elimination mechanism. - **h. S_N1 Nucleophilic substitution**: Unimolecular nucleophilic substitution. - **i. S_N2 Nucleophilic substitution**: Bimolecular nucleophilic substitution. - **j. Electrophilic aromatic substitution**: Substitution on an aromatic ring via an electrophile. #### Exercise Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers. 1. ______________ 2. ______________ **Explanation of Diagrams:** - **Diagram 1**: Shows an alcohol group (-OH) on cyclohexane reacting with HBr, resulting in a carbocation and a bromide ion. - **Diagram 2**: Illustrates an alkene with a phenyl group reacting with brom
### Educational Resource: Reaction Mechanisms Identification #### Reaction Examples and Mechanism Identification Consider the following two chemical reactions: #### Reaction 1. \[ \text{CH}_3\text{CH}_2\text{OH} + \text{HI} \rightarrow \text{CH}_3\text{CH}_2\text{I} + \text{H}_2\text{O} \] #### Reaction 2. \[ \begin{array}{c} \text{Ph}\text{CH}_2\text{CH}_2\text{OCH}_3\text{NM}_2 + \text{H}_2\text{SO}_4 \rightarrow \\ \text{Ph}\text{CH}_2\text{CH}_2\text{OH}\text{Tamoxifen} \: (\text{anti (breast) cancer drug}) \end{array} \] &nbsp; #### Mechanism Types Assign the correct mechanism type for each reaction from the options below: **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>N</sub>1 Nucleophilic substitution **i.** S<sub>N</sub>2 Nucleophilic substitution **j.** Electrophilic aromatic substitution &nbsp; **Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers.** **1.** **2.** --- #### Explanation of Graphs/Diagrams **Graph/Diagram 1:** Illustrates the conversion of ethanol to ethyl iodide and water. This reaction involves the substitution of the hydroxyl group (-OH) in ethanol with an iodine atom (I). **Graph/Diagram 2:** Depicts the conversion of a stilbene oxide derivative to Tamoxifen, a well-known anti-breast cancer drug, in the presence of sulfuric acid. The reaction showcases the opening of the oxirane (epoxide) ring and rearrangement to form the final product, Tamoxifen. --- Please identify the mechanisms and type the corresponding letters from a - j in the provided boxes. **1.
Transcribed Image Text:### Educational Resource: Reaction Mechanisms Identification #### Reaction Examples and Mechanism Identification Consider the following two chemical reactions: #### Reaction 1. \[ \text{CH}_3\text{CH}_2\text{OH} + \text{HI} \rightarrow \text{CH}_3\text{CH}_2\text{I} + \text{H}_2\text{O} \] #### Reaction 2. \[ \begin{array}{c} \text{Ph}\text{CH}_2\text{CH}_2\text{OCH}_3\text{NM}_2 + \text{H}_2\text{SO}_4 \rightarrow \\ \text{Ph}\text{CH}_2\text{CH}_2\text{OH}\text{Tamoxifen} \: (\text{anti (breast) cancer drug}) \end{array} \] &nbsp; #### Mechanism Types Assign the correct mechanism type for each reaction from the options below: **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>N</sub>1 Nucleophilic substitution **i.** S<sub>N</sub>2 Nucleophilic substitution **j.** Electrophilic aromatic substitution &nbsp; **Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers.** **1.** **2.** --- #### Explanation of Graphs/Diagrams **Graph/Diagram 1:** Illustrates the conversion of ethanol to ethyl iodide and water. This reaction involves the substitution of the hydroxyl group (-OH) in ethanol with an iodine atom (I). **Graph/Diagram 2:** Depicts the conversion of a stilbene oxide derivative to Tamoxifen, a well-known anti-breast cancer drug, in the presence of sulfuric acid. The reaction showcases the opening of the oxirane (epoxide) ring and rearrangement to form the final product, Tamoxifen. --- Please identify the mechanisms and type the corresponding letters from a - j in the provided boxes. **1.
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