Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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### Organic Chemistry Reaction Mechanisms: Worksheet

#### Instructions:
i) Predict the product(s) for the major mechanistic pathway(s). Show stereochemistry where applicable. If a racemate forms, draw one isomer and write "racemate."
(This means that if there is an elimination, you only need to draw the major product of that. Or if there is a mixture of mechanism types, you would need the major product for each of the types.)

ii) Write if the mechanism goes by \( S_{N}2 \), \( S_{N}1 \), E2, and/or E1.

#### Reactions:
- **Figure A:**

  A molecule has a Bromine (Br) atom attached to a secondary carbon. It is subjected to a reaction with Sodium Cyanide (NaCN).

  **Reaction Mechanism**: \( S_{N}2 \) (Typically the \( S_{N}2 \) mechanism occurs with a strong nucleophile like NaCN)

  **Expected Product**:
  - The Bromine (Br) will be substituted by the Cyanide (CN) group.

- **Figure B:**

  A cyclic molecule with a Bromine (Br) atom attached to a secondary carbon is subjected to a reaction with Methanol (CH\(_3\)OH).

  **Reaction Mechanism**: \( S_{N}1 \) (Typically the \( S_{N}1 \) mechanism occurs with a weak nucleophile like CH\(_3\)OH and could proceed with carbocation formation).

  **Expected Product**:
  - The Bromine (Br) will be substituted by the Methoxy (OCH\(_3\)) group. 

### Diagrams:
- Both figures A and B show the structure of the organic molecules before the reaction. The Br (Bromine) atom has been placed on a secondary carbon and is represented in wedge notation to indicate stereochemistry.

#### Note:
* Ensure that in practical applications you consider the reaction conditions and solvents, as they can dramatically influence the pathway (SN2 vs SN1, E2 vs E1).
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Transcribed Image Text:### Organic Chemistry Reaction Mechanisms: Worksheet #### Instructions: i) Predict the product(s) for the major mechanistic pathway(s). Show stereochemistry where applicable. If a racemate forms, draw one isomer and write "racemate." (This means that if there is an elimination, you only need to draw the major product of that. Or if there is a mixture of mechanism types, you would need the major product for each of the types.) ii) Write if the mechanism goes by \( S_{N}2 \), \( S_{N}1 \), E2, and/or E1. #### Reactions: - **Figure A:** A molecule has a Bromine (Br) atom attached to a secondary carbon. It is subjected to a reaction with Sodium Cyanide (NaCN). **Reaction Mechanism**: \( S_{N}2 \) (Typically the \( S_{N}2 \) mechanism occurs with a strong nucleophile like NaCN) **Expected Product**: - The Bromine (Br) will be substituted by the Cyanide (CN) group. - **Figure B:** A cyclic molecule with a Bromine (Br) atom attached to a secondary carbon is subjected to a reaction with Methanol (CH\(_3\)OH). **Reaction Mechanism**: \( S_{N}1 \) (Typically the \( S_{N}1 \) mechanism occurs with a weak nucleophile like CH\(_3\)OH and could proceed with carbocation formation). **Expected Product**: - The Bromine (Br) will be substituted by the Methoxy (OCH\(_3\)) group. ### Diagrams: - Both figures A and B show the structure of the organic molecules before the reaction. The Br (Bromine) atom has been placed on a secondary carbon and is represented in wedge notation to indicate stereochemistry. #### Note: * Ensure that in practical applications you consider the reaction conditions and solvents, as they can dramatically influence the pathway (SN2 vs SN1, E2 vs E1).
### Organic Chemistry Reactions Overview

### Reaction Analysis


#### Reaction B:
The structure shown consists of a cycloalkane ring where one of the carbon atoms is bonded to a bromine atom (Br).

**Reagent:** CH₃OH (Methanol)

**Diagram description:**
- A cycloalkane with the molecular formula including a bromine substituent.
- An arrow indicating the reaction direction, labeled with CH₃OH.

**Interpretation:**
The given reaction suggests a substitution where methanol likely acts as a nucleophile, replacing the bromine atom on the cycloalkane.

---

#### Reaction C:
The structure depicted is a straight-chain alkyl group terminated with a carbon-bromine (C-Br) bond.

**Reagent:** (CH₃)₃OK (Potassium tert-butoxide)

**Diagram description:**
- A straight-chain carbon skeleton with a bromine substituent.
- A reaction arrow labeled with (CH₃)₃OK indicating the direction of the reaction.

**Interpretation:**
This is likely an elimination reaction where potassium tert-butoxide induces the removal of the bromine atom, leading to the formation of an alkene due to the strong basic nature of the reagent.

### Summary
These reactions demonstrate common organic chemistry transformations — nucleophilic substitution and elimination — with specific reagents (methanol and potassium tert-butoxide) to achieve the desired chemical changes.
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Transcribed Image Text:### Organic Chemistry Reactions Overview ### Reaction Analysis #### Reaction B: The structure shown consists of a cycloalkane ring where one of the carbon atoms is bonded to a bromine atom (Br). **Reagent:** CH₃OH (Methanol) **Diagram description:** - A cycloalkane with the molecular formula including a bromine substituent. - An arrow indicating the reaction direction, labeled with CH₃OH. **Interpretation:** The given reaction suggests a substitution where methanol likely acts as a nucleophile, replacing the bromine atom on the cycloalkane. --- #### Reaction C: The structure depicted is a straight-chain alkyl group terminated with a carbon-bromine (C-Br) bond. **Reagent:** (CH₃)₃OK (Potassium tert-butoxide) **Diagram description:** - A straight-chain carbon skeleton with a bromine substituent. - A reaction arrow labeled with (CH₃)₃OK indicating the direction of the reaction. **Interpretation:** This is likely an elimination reaction where potassium tert-butoxide induces the removal of the bromine atom, leading to the formation of an alkene due to the strong basic nature of the reagent. ### Summary These reactions demonstrate common organic chemistry transformations — nucleophilic substitution and elimination — with specific reagents (methanol and potassium tert-butoxide) to achieve the desired chemical changes.
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