Predict the product(s): CI

Chemistry
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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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### Nitration of 1,4-Dichlorobenzene

**Objective: Predict the product(s) of the nitration reaction.**

**Reaction:**

1,4-Dichlorobenzene reacts with nitric acid in the presence of sulfuric acid, according to the following scheme:
   
   \[
   \text{1,4-Dichlorobenzene} + \text{HNO}_3 \xrightarrow{\text{H}_2\text{SO}_4} \text{Product(s)}
   \]

**Reactant:**
 
A benzene ring with two chlorine (Cl) substituents at positions 1 and 4.

**Options for Product(s):**

1. **Structure 1:**
   - Chlorine substituent at position 1
   - Nitrogen dioxide (NO₂) substituent at position 2
   - Chlorine substituent at position 4

2. **Structure 2:**
   - Chlorine substituent at position 1
   - Chlorine substituent at position 4
   - Nitrogen dioxide (NO₂) substituent at position 3

### Explanation of Reaction Mechanism:

The nitration of benzene derivatives typically yields nitro groups placed ortho- or para- to existing substituents due to the electron-withdrawing effects of groups like chlorine. 

Given the starting material 1,4-Dichlorobenzene, nitric acid (HNO₃) will introduce a nitro group (NO₂) onto the benzene ring in the presence of sulfuric acid (H₂SO₄).

### Diagrams:

The diagrams illustrate the possible products of the reaction:
- Both diagrams depict a benzene ring with substituents.
- Positions on the ring are numbered relative to the position of the chlorine atoms.

By predicting the product, we determine into which available positions the nitro group will be placed considering the nature of the chlorinated benzene ring.
Transcribed Image Text:### Nitration of 1,4-Dichlorobenzene **Objective: Predict the product(s) of the nitration reaction.** **Reaction:** 1,4-Dichlorobenzene reacts with nitric acid in the presence of sulfuric acid, according to the following scheme: \[ \text{1,4-Dichlorobenzene} + \text{HNO}_3 \xrightarrow{\text{H}_2\text{SO}_4} \text{Product(s)} \] **Reactant:** A benzene ring with two chlorine (Cl) substituents at positions 1 and 4. **Options for Product(s):** 1. **Structure 1:** - Chlorine substituent at position 1 - Nitrogen dioxide (NO₂) substituent at position 2 - Chlorine substituent at position 4 2. **Structure 2:** - Chlorine substituent at position 1 - Chlorine substituent at position 4 - Nitrogen dioxide (NO₂) substituent at position 3 ### Explanation of Reaction Mechanism: The nitration of benzene derivatives typically yields nitro groups placed ortho- or para- to existing substituents due to the electron-withdrawing effects of groups like chlorine. Given the starting material 1,4-Dichlorobenzene, nitric acid (HNO₃) will introduce a nitro group (NO₂) onto the benzene ring in the presence of sulfuric acid (H₂SO₄). ### Diagrams: The diagrams illustrate the possible products of the reaction: - Both diagrams depict a benzene ring with substituents. - Positions on the ring are numbered relative to the position of the chlorine atoms. By predicting the product, we determine into which available positions the nitro group will be placed considering the nature of the chlorinated benzene ring.
### Example of Molecular Structures with Halogens and Nitro Groups

Below are two chemical structures, each featuring chlorinated aromatic compounds. Understanding the arrangement of these substituents on the benzene ring is crucial in organic chemistry for grasping their chemical reactivity and properties.

#### Structure 1:
- **Description**: This is a monosubstituted benzene ring with three substituents: two chlorine (Cl) atoms and one nitro (NO₂) group.
- **Substituents**: 
  - A chlorine (Cl) atom is positioned at the 1 and 3 positions relative to each other.
  - A nitro (NO₂) group is attached at the 4-position.
- **Representation**:
  - The aromatic ring (benzene) is depicted as a hexagon with alternating double bonds.
  - Each vertex represents a carbon atom, with hydrogen atoms implied to fill the remaining valency of each carbon.

#### Structure 2:
- **Description**: This is a biphenyl compound, consisting of two benzene rings bonded together. The rings have multiple chlorine (Cl) substituents.
- **Substituents**:
  - The first benzene ring has a chlorine (Cl) atom at the 4-position.
  - The second benzene ring (directly connected to the first) has chlorine atoms at the 2- and 6-positions.
- **Representation**:
  - The biphenyl structure indicates two hexagonal rings fused together.
  - Similar to the first structure, the vertexes represent carbon atoms with implied hydrogen atoms to complete their valence electrons.

It is important for students to recognize the difference in reactivity and properties, influenced by substituent positions and types. Understanding these structures can greatly aid in the synthesis and analysis of complex organic compounds.
Transcribed Image Text:### Example of Molecular Structures with Halogens and Nitro Groups Below are two chemical structures, each featuring chlorinated aromatic compounds. Understanding the arrangement of these substituents on the benzene ring is crucial in organic chemistry for grasping their chemical reactivity and properties. #### Structure 1: - **Description**: This is a monosubstituted benzene ring with three substituents: two chlorine (Cl) atoms and one nitro (NO₂) group. - **Substituents**: - A chlorine (Cl) atom is positioned at the 1 and 3 positions relative to each other. - A nitro (NO₂) group is attached at the 4-position. - **Representation**: - The aromatic ring (benzene) is depicted as a hexagon with alternating double bonds. - Each vertex represents a carbon atom, with hydrogen atoms implied to fill the remaining valency of each carbon. #### Structure 2: - **Description**: This is a biphenyl compound, consisting of two benzene rings bonded together. The rings have multiple chlorine (Cl) substituents. - **Substituents**: - The first benzene ring has a chlorine (Cl) atom at the 4-position. - The second benzene ring (directly connected to the first) has chlorine atoms at the 2- and 6-positions. - **Representation**: - The biphenyl structure indicates two hexagonal rings fused together. - Similar to the first structure, the vertexes represent carbon atoms with implied hydrogen atoms to complete their valence electrons. It is important for students to recognize the difference in reactivity and properties, influenced by substituent positions and types. Understanding these structures can greatly aid in the synthesis and analysis of complex organic compounds.
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