Drawing Arrows ... < dilute NaOH DMSO :OH: > Na Ⓒ :Br:0 :Br: Undo Reset Ⓒ Done Na+ H Drag To Pan

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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The image illustrates a chemical reaction mechanism. Here is a detailed transcription and explanation:

1. **Chemical Structures**:
   - The initial structure on the right shows a bromine-substituted alkane with a carbon chain. The bromine atom (Br) is connected to a secondary carbon.
   - Next to it is the structure of sodium hydroxide (NaOH), with Na⁺ depicted separately and hydroxide ion (HO⁻) drawn with lone pairs on the oxygen.

2. **Reaction Conditions**:
   - An arrow points towards the product, indicating the reaction proceeds in the presence of "dilute NaOH" and "DMSO" (dimethyl sulfoxide as a solvent).

3. **Product Structure**:
   - The resulting product, shown after the arrow, is an alcohol. The OH group has replaced the bromine atom in the structure.

4. **Mechanism Overview**:
   - This reaction illustrates a nucleophilic substitution mechanism (likely SN2), where the hydroxide ion attacks the carbon bonded to bromine, resulting in the formation of an alcohol and the expulsion of the bromide ion (Br⁻).

This detailed reaction showcases the transformation of an alkyl halide to an alcohol, highlighting the role of nucleophiles and suitable solvents in facilitating substitution reactions.
Transcribed Image Text:The image illustrates a chemical reaction mechanism. Here is a detailed transcription and explanation: 1. **Chemical Structures**: - The initial structure on the right shows a bromine-substituted alkane with a carbon chain. The bromine atom (Br) is connected to a secondary carbon. - Next to it is the structure of sodium hydroxide (NaOH), with Na⁺ depicted separately and hydroxide ion (HO⁻) drawn with lone pairs on the oxygen. 2. **Reaction Conditions**: - An arrow points towards the product, indicating the reaction proceeds in the presence of "dilute NaOH" and "DMSO" (dimethyl sulfoxide as a solvent). 3. **Product Structure**: - The resulting product, shown after the arrow, is an alcohol. The OH group has replaced the bromine atom in the structure. 4. **Mechanism Overview**: - This reaction illustrates a nucleophilic substitution mechanism (likely SN2), where the hydroxide ion attacks the carbon bonded to bromine, resulting in the formation of an alcohol and the expulsion of the bromide ion (Br⁻). This detailed reaction showcases the transformation of an alkyl halide to an alcohol, highlighting the role of nucleophiles and suitable solvents in facilitating substitution reactions.
### Electron-Pushing Mechanisms: Curved Arrows Tutorial

Curved arrows are used to illustrate the flow of electrons in chemical reactions. This educational resource provides a step-by-step guide to drawing curved electron-pushing arrows for the following reaction. Focus on accounting for all bond-breaking and bond-making steps.

#### Materials Needed:
- **Reagents**: Dilute NaOH
- **Solvent**: DMSO

#### Reaction Setup:
On the right, the starting structure is a halogenated organic compound with a bromine atom attached (represented by a wedge, indicating stereochemistry). Next to it, there is a sodium cation (\( \text{Na}^+ \)) and a negatively charged oxygen molecule bonded to a hydrogen atom, signifying an alkoxide ion.

#### Task:
1. **Using the given structures**:
   - Identify where electrons will flow.
   - Use curved arrows to depict electron movement.
   - Ensure each step shows how bonds are broken and formed.

2. **Considerations**:
   - Start from electron-rich areas (lone pairs or negative charges).
   - Point arrows toward electron-deficient areas (such as electron-deficient carbons or positive charges).

3. **Reaction Condition**: 
   - Conduct the reaction in dilute NaOH, in DMSO, facilitating nucleophilic substitution or elimination.

This exercise aids in understanding reaction mechanisms crucial for organic chemistry studies.
Transcribed Image Text:### Electron-Pushing Mechanisms: Curved Arrows Tutorial Curved arrows are used to illustrate the flow of electrons in chemical reactions. This educational resource provides a step-by-step guide to drawing curved electron-pushing arrows for the following reaction. Focus on accounting for all bond-breaking and bond-making steps. #### Materials Needed: - **Reagents**: Dilute NaOH - **Solvent**: DMSO #### Reaction Setup: On the right, the starting structure is a halogenated organic compound with a bromine atom attached (represented by a wedge, indicating stereochemistry). Next to it, there is a sodium cation (\( \text{Na}^+ \)) and a negatively charged oxygen molecule bonded to a hydrogen atom, signifying an alkoxide ion. #### Task: 1. **Using the given structures**: - Identify where electrons will flow. - Use curved arrows to depict electron movement. - Ensure each step shows how bonds are broken and formed. 2. **Considerations**: - Start from electron-rich areas (lone pairs or negative charges). - Point arrows toward electron-deficient areas (such as electron-deficient carbons or positive charges). 3. **Reaction Condition**: - Conduct the reaction in dilute NaOH, in DMSO, facilitating nucleophilic substitution or elimination. This exercise aids in understanding reaction mechanisms crucial for organic chemistry studies.
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