Curved arrows are used to illustrate the flow of electrons. Follow the curved arrows and draw the product of an SN2 reaction shown below. Include all lone pairs and charges as appropriate. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. H3C- THF > H CH3

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**Problem 20 of 50**

### Instructions

Curved arrows are used to illustrate the flow of electrons. Follow the curved arrows and draw the product of an SN2 reaction shown below.

Include all lone pairs and charges as appropriate. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts.

### Diagram Explanation

The diagram shows a nucleophilic substitution reaction, specifically an SN2 mechanism:

1. **Reactants:**
   - A methoxide ion (H₃C–O⁻) with a negative charge on the oxygen.
   - A secondary alkyl chloride compound with the chloride (Cl⁻) as the leaving group.

2. **Curved Arrows:**
   - The first curved arrow originates from the lone pair on the oxygen in methoxide, showing it attacking the carbon atom bonded to the chlorine.
   - The second curved arrow indicates the movement of electron pairs, with chlorine leaving as Cl⁻.

3. **Stereochemistry:**
   - Wedge and dash bonds are used to show the three-dimensional arrangement of atoms. The carbon originally had a chlorine attached with a dash (behind the plane), showing inversion of configuration typical of SN2 reactions.

4. **Solvent:**
   - Tetrahydrofuran (THF) is indicated below the reaction.

This setup exemplifies the concerted, single-step mechanism of SN2, resulting in a backside attack that leads to inversion of stereochemistry.
Transcribed Image Text:**Problem 20 of 50** ### Instructions Curved arrows are used to illustrate the flow of electrons. Follow the curved arrows and draw the product of an SN2 reaction shown below. Include all lone pairs and charges as appropriate. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. ### Diagram Explanation The diagram shows a nucleophilic substitution reaction, specifically an SN2 mechanism: 1. **Reactants:** - A methoxide ion (H₃C–O⁻) with a negative charge on the oxygen. - A secondary alkyl chloride compound with the chloride (Cl⁻) as the leaving group. 2. **Curved Arrows:** - The first curved arrow originates from the lone pair on the oxygen in methoxide, showing it attacking the carbon atom bonded to the chlorine. - The second curved arrow indicates the movement of electron pairs, with chlorine leaving as Cl⁻. 3. **Stereochemistry:** - Wedge and dash bonds are used to show the three-dimensional arrangement of atoms. The carbon originally had a chlorine attached with a dash (behind the plane), showing inversion of configuration typical of SN2 reactions. 4. **Solvent:** - Tetrahydrofuran (THF) is indicated below the reaction. This setup exemplifies the concerted, single-step mechanism of SN2, resulting in a backside attack that leads to inversion of stereochemistry.
# Educational Content on Nucleophilic Substitution Reaction

## Problem 20 of 50

### Description

This diagram depicts a nucleophilic substitution reaction mechanism.

### Reaction Details

- **Starting Materials**: In the top box, a molecule is shown with a methoxide ion (\( \text{H}_3\text{CO}^- \)) acting as a nucleophile. This nucleophile has a lone pair of electrons highlighted.
- **Target Molecule**: The target is a secondary alkyl chloride where the chlorine atom is bonded to a central carbon, along with a hydrogen and a methyl group (\( \text{CH}_3 \)).
- **Reaction Mechanism**: 
  - A blue curved arrow indicates the movement of a pair of electrons from the oxygen atom in methoxide towards the electrophilic carbon attached to the chlorine.
  - Another blue arrow shows the electrons from the C-Cl bond moving towards the chlorine atom, resulting in the departure of chloride ion (\( \text{Cl}^- \)).

- **Intermediate Step**: The reaction occurs in the presence of tetrahydrofuran (THF), a common solvent used in such reactions to stabilize charge build-up.

### Product

- The bottom dashed box shows the expected product after the nucleophilic substitution: a cyclic structure labeled "Select to Edit". The new bond forms with the methoxide ion, replacing the chlorine atom. 

This representation emphasizes the mechanism where a nucleophile replaces a leaving group on an electrophilic center.
Transcribed Image Text:# Educational Content on Nucleophilic Substitution Reaction ## Problem 20 of 50 ### Description This diagram depicts a nucleophilic substitution reaction mechanism. ### Reaction Details - **Starting Materials**: In the top box, a molecule is shown with a methoxide ion (\( \text{H}_3\text{CO}^- \)) acting as a nucleophile. This nucleophile has a lone pair of electrons highlighted. - **Target Molecule**: The target is a secondary alkyl chloride where the chlorine atom is bonded to a central carbon, along with a hydrogen and a methyl group (\( \text{CH}_3 \)). - **Reaction Mechanism**: - A blue curved arrow indicates the movement of a pair of electrons from the oxygen atom in methoxide towards the electrophilic carbon attached to the chlorine. - Another blue arrow shows the electrons from the C-Cl bond moving towards the chlorine atom, resulting in the departure of chloride ion (\( \text{Cl}^- \)). - **Intermediate Step**: The reaction occurs in the presence of tetrahydrofuran (THF), a common solvent used in such reactions to stabilize charge build-up. ### Product - The bottom dashed box shows the expected product after the nucleophilic substitution: a cyclic structure labeled "Select to Edit". The new bond forms with the methoxide ion, replacing the chlorine atom. This representation emphasizes the mechanism where a nucleophile replaces a leaving group on an electrophilic center.
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