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.
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.
Chemistry
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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
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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. **](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F4167b07b-ab2c-42e3-ab89-9f12261de975%2F59943792-dda2-406f-9552-2c29b84327df%2Fgs14jbu_processed.png&w=3840&q=75)
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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