Chem 730: Organic Chemistry 1H Problem Set 5: Chap. 9 & 10 (40 points) Due Friday, November 12 Exercise 1 Provide a mechanism for the following reactions. Provide an explanation for the selectivity exhibited by the first reaction. OH HBr 86 14 HCI (b) Exercise 2 Diaronium ions (-N are siuch powerful leaving groups that they offer a method for generating

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Provide a mechanism for the following reaction. Provide a Mechanism.

**Chem 730: Organic Chemistry 1H**

**Problem Set 5: Chap. 9 & 10 (40 points)**

*Due: Friday, November 12*

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**Exercise 1**

Provide a mechanism for the following reactions. Provide an explanation for the selectivity exhibited by the first reaction.

(a) Reaction involves a primary alcohol reacting with HBr to form a bromoalkane. The chemical equation is:
\[ \text{CH}_3\text{OH} + \text{HBr} \rightarrow \text{CH}_3\text{Br} + \text{H}_2\text{O} \]

(b) Reaction shows cyclobutane reacting with HCl to form an alkyl chloride:
\[ \Box + \text{HCl} \rightarrow \text{Cl}\text{-Cyclobutane} \]

**Exercise 2**

Diazonium ions (\(R\)-\(N_2^+\)) are such powerful leaving groups that they offer a method for generating… [incomplete text]

[Note: The partial text indicates that more context is necessary to complete Exercise 2, possibly involving reactions or examples related to diazonium ions.]

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**Explanation:**

- **Diagram (a)**: Illustrates the conversion of alcohol to a bromoalkane through protonation and subsequent nucleophilic substitution.
- **Diagram (b)**: Demonstrates the substitution reaction of HCl with cyclobutane to yield a chloro-substituted cyclobutane.

The document appears to be educational material focusing on reaction mechanisms and selectivity in organic chemistry, providing practical problem-solving exercises for students.
Transcribed Image Text:**Chem 730: Organic Chemistry 1H** **Problem Set 5: Chap. 9 & 10 (40 points)** *Due: Friday, November 12* --- **Exercise 1** Provide a mechanism for the following reactions. Provide an explanation for the selectivity exhibited by the first reaction. (a) Reaction involves a primary alcohol reacting with HBr to form a bromoalkane. The chemical equation is: \[ \text{CH}_3\text{OH} + \text{HBr} \rightarrow \text{CH}_3\text{Br} + \text{H}_2\text{O} \] (b) Reaction shows cyclobutane reacting with HCl to form an alkyl chloride: \[ \Box + \text{HCl} \rightarrow \text{Cl}\text{-Cyclobutane} \] **Exercise 2** Diazonium ions (\(R\)-\(N_2^+\)) are such powerful leaving groups that they offer a method for generating… [incomplete text] [Note: The partial text indicates that more context is necessary to complete Exercise 2, possibly involving reactions or examples related to diazonium ions.] --- **Explanation:** - **Diagram (a)**: Illustrates the conversion of alcohol to a bromoalkane through protonation and subsequent nucleophilic substitution. - **Diagram (b)**: Demonstrates the substitution reaction of HCl with cyclobutane to yield a chloro-substituted cyclobutane. The document appears to be educational material focusing on reaction mechanisms and selectivity in organic chemistry, providing practical problem-solving exercises for students.
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