1. Draw a generic carbocation intermediate, *CR3. 2. What are the R-C-R bond angles in *CR3? 3. What is the shape of *CR3?

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**Supplement to ChemActivity 9, Part A: Bromonium Ion**

**CHE 210**

**Goal:**  
How do we explain why some electrophilic addition reactions to alkenes produce a mixture of products, whereas others result only in trans products?

**Case #1: HX Addition to an Alkene**

**Critical Thinking Questions**

1. **Draw a generic carbocation intermediate, *CR₃*.**

2. **What are the R—C—R bond angles in *CR₃*?**

3. **What is the shape of *CR₃*?**

4. **What is the hybridization of the central carbon atom in *CR₃*?**

5. **Which type of hybrid orbitals on the central carbon atom are used to make the C—R bonds?**

6. **Which orbital is “left over” after the three C—R bonds have been formed?**  
   *(Hint: This is not a hybrid orbital.)*

7. **Draw the curved arrows showing movement of electrons for the reaction below (same as the first reaction in Alkene Mechanism Worksheet 2). In each step, identify the nucleophile (Nu) and the electrophile (E).**  
   (*Note: “D” stands for deuterium or “heavy hydrogen”. For more information about deuterium, see ChemActivity 9, Part B, Model 6: Isotopic Labeling, on page 135 of the workbook.*)

   **Diagram Explanation**  
   - The diagram shows an alkene reacting with D—Cl in the presence of ether.  
   - The reaction results in two products: a "cis" isomer and a "trans" isomer.  
   - The movement of electrons is depicted with curved arrows.  
   - The nucleophile and electrophile are identified in each reaction step.

8. **In one well-written sentence, explain how it is possible to end up with both “cis” and “trans” products shown above.**
Transcribed Image Text:**Supplement to ChemActivity 9, Part A: Bromonium Ion** **CHE 210** **Goal:** How do we explain why some electrophilic addition reactions to alkenes produce a mixture of products, whereas others result only in trans products? **Case #1: HX Addition to an Alkene** **Critical Thinking Questions** 1. **Draw a generic carbocation intermediate, *CR₃*.** 2. **What are the R—C—R bond angles in *CR₃*?** 3. **What is the shape of *CR₃*?** 4. **What is the hybridization of the central carbon atom in *CR₃*?** 5. **Which type of hybrid orbitals on the central carbon atom are used to make the C—R bonds?** 6. **Which orbital is “left over” after the three C—R bonds have been formed?** *(Hint: This is not a hybrid orbital.)* 7. **Draw the curved arrows showing movement of electrons for the reaction below (same as the first reaction in Alkene Mechanism Worksheet 2). In each step, identify the nucleophile (Nu) and the electrophile (E).** (*Note: “D” stands for deuterium or “heavy hydrogen”. For more information about deuterium, see ChemActivity 9, Part B, Model 6: Isotopic Labeling, on page 135 of the workbook.*) **Diagram Explanation** - The diagram shows an alkene reacting with D—Cl in the presence of ether. - The reaction results in two products: a "cis" isomer and a "trans" isomer. - The movement of electrons is depicted with curved arrows. - The nucleophile and electrophile are identified in each reaction step. 8. **In one well-written sentence, explain how it is possible to end up with both “cis” and “trans” products shown above.**
**Alkene Mechanism Worksheet 2: Br₂ Addition & Halohydrin Formation - CHE 210**

**Stereochemistry of HX Addition to an Alkene**

1. The reaction begins with an alkene reacting with D—Cl in ether. The hydrogen and deuterium atoms add across the double bond, with deuterium being shown on a wedge to indicate stereochemistry.
2. Two possible stereochemical products are depicted: the addition of deuterium and chloride across the double bond can result in either the "cis" or "trans" configuration.

**Stereochemistry and Regiochemistry of Addition of Br₂ to an Alkene**

1. This reaction involves an alkene reacting with molecular bromine (Br₂) in dichloromethane (CH₂Cl₂). The bromine molecule forms a bromonium ion intermediate shown with a cyclic structure.
2. The final product is the addition of bromine atoms across the alkene, where the stereochemistry is depicted with solid and dashed wedges, indicating different spatial orientations.

**Stereochemistry and Regiochemistry of Halohydrin Formation**

1. An alkene reacts with Br₂ in the presence of water (H₂O). The bromonium ion intermediate opens up due to the attack by water.
2. The final product is a halohydrin, with bromine and hydroxyl (OH) groups added across the double bond. The diagram includes charges and lone pairs to indicate electron distribution.

**Additional Information:**

- A note indicates that two sets of reagents can accomplish the above transformation:
  - Br₂/H₂O or
  - NBS/H₂O/DMSO.
  
- A diagram shows the structure of N-bromosuccinimide (NBS) and dimethyl sulfoxide (DMSO), depicting their molecular structures with lone pairs and charges where applicable.

**A. L. Smith 2021**
Transcribed Image Text:**Alkene Mechanism Worksheet 2: Br₂ Addition & Halohydrin Formation - CHE 210** **Stereochemistry of HX Addition to an Alkene** 1. The reaction begins with an alkene reacting with D—Cl in ether. The hydrogen and deuterium atoms add across the double bond, with deuterium being shown on a wedge to indicate stereochemistry. 2. Two possible stereochemical products are depicted: the addition of deuterium and chloride across the double bond can result in either the "cis" or "trans" configuration. **Stereochemistry and Regiochemistry of Addition of Br₂ to an Alkene** 1. This reaction involves an alkene reacting with molecular bromine (Br₂) in dichloromethane (CH₂Cl₂). The bromine molecule forms a bromonium ion intermediate shown with a cyclic structure. 2. The final product is the addition of bromine atoms across the alkene, where the stereochemistry is depicted with solid and dashed wedges, indicating different spatial orientations. **Stereochemistry and Regiochemistry of Halohydrin Formation** 1. An alkene reacts with Br₂ in the presence of water (H₂O). The bromonium ion intermediate opens up due to the attack by water. 2. The final product is a halohydrin, with bromine and hydroxyl (OH) groups added across the double bond. The diagram includes charges and lone pairs to indicate electron distribution. **Additional Information:** - A note indicates that two sets of reagents can accomplish the above transformation: - Br₂/H₂O or - NBS/H₂O/DMSO. - A diagram shows the structure of N-bromosuccinimide (NBS) and dimethyl sulfoxide (DMSO), depicting their molecular structures with lone pairs and charges where applicable. **A. L. Smith 2021**
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