2. (from Review) Propose a sequence of reagents for the following transformation [Chapter 11, section 11.3] involving changes to the carbon skeleton. Br Br- NC.

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2. **(from Review)** Propose a sequence of reagents for the following transformation [Chapter 11, section 11.3] involving changes to the carbon skeleton.

### Description and Explanation

The given sequence diagram illustrates the step-by-step chemical transformation of a hydrocarbon involving carbon skeleton rearrangements, as described in Chapter 11, Section 11.3 of the study material. Below, each step and the corresponding structural change are outlined:

1. **Starting Material**: 
   - The first structure is a simple hydrocarbon with the formula \(\ce{CH3-CH(CH3)-CH2-CH3}\).

2. **First Transformation**:
   - The first step involves the introduction of a bromine atom through a substitution reaction, resulting in the compound \(\ce{(CH3)2CBr-CH2-CH3}\).

3. **Second Transformation**:
   - The next step converts the bromoalkane to an alkene via an elimination reaction, yielding \(\ce{(CH3)2C=CH-CH3}\).

4. **Third Transformation**:
   - The alkene then undergoes a reaction that rearranges the carbon skeleton, forming a new structure \(\ce{CH3-CH=C(CH3)-CH3}\).

5. **Fourth Transformation**:
   - Another substitution reaction occurs, reintroducing a bromine atom into the rearranged alkene, producing \(\ce{CH3-CH2-CBr(CH3)-CH3}\).

6. **Fifth Transformation**:
   - Finally, the brominated compound undergoes a nucleophilic substitution where a nitrile group (\(\ce{CN}\)) replaces the bromine, resulting in the final product \(\ce{CH3-CH2-C(CN)(CH3)-CH3}\).

### Visualization of Transformations

To summarize, the sequence of reactions involves the following transformations and chemical reagents:

1. **Initial Hydrocarbon State**:
   \[
   \ce{CH3-CH(CH3)-CH2-CH3}
   \]
   → (Bromination, \(\ce{Br2}\))

2. **Formation of Bromoalkane**:
   \[
   \ce{(CH3)2CBr-CH2-CH3}
   \]
   → (Elimination, \(\ce{EtOH}\))

3. **
Transcribed Image Text:2. **(from Review)** Propose a sequence of reagents for the following transformation [Chapter 11, section 11.3] involving changes to the carbon skeleton. ### Description and Explanation The given sequence diagram illustrates the step-by-step chemical transformation of a hydrocarbon involving carbon skeleton rearrangements, as described in Chapter 11, Section 11.3 of the study material. Below, each step and the corresponding structural change are outlined: 1. **Starting Material**: - The first structure is a simple hydrocarbon with the formula \(\ce{CH3-CH(CH3)-CH2-CH3}\). 2. **First Transformation**: - The first step involves the introduction of a bromine atom through a substitution reaction, resulting in the compound \(\ce{(CH3)2CBr-CH2-CH3}\). 3. **Second Transformation**: - The next step converts the bromoalkane to an alkene via an elimination reaction, yielding \(\ce{(CH3)2C=CH-CH3}\). 4. **Third Transformation**: - The alkene then undergoes a reaction that rearranges the carbon skeleton, forming a new structure \(\ce{CH3-CH=C(CH3)-CH3}\). 5. **Fourth Transformation**: - Another substitution reaction occurs, reintroducing a bromine atom into the rearranged alkene, producing \(\ce{CH3-CH2-CBr(CH3)-CH3}\). 6. **Fifth Transformation**: - Finally, the brominated compound undergoes a nucleophilic substitution where a nitrile group (\(\ce{CN}\)) replaces the bromine, resulting in the final product \(\ce{CH3-CH2-C(CN)(CH3)-CH3}\). ### Visualization of Transformations To summarize, the sequence of reactions involves the following transformations and chemical reagents: 1. **Initial Hydrocarbon State**: \[ \ce{CH3-CH(CH3)-CH2-CH3} \] → (Bromination, \(\ce{Br2}\)) 2. **Formation of Bromoalkane**: \[ \ce{(CH3)2CBr-CH2-CH3} \] → (Elimination, \(\ce{EtOH}\)) 3. **
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