Chapter17: Alcohols And Phenols
Section17.SE: Something Extra
Problem 71AP: A problem often encountered in the oxidation of primary alcohols to acids is that esters are...
Related questions
Question
What would be the major and minor product(s) of this reaction?

Transcribed Image Text:### Reaction Analysis
**Reaction Description:**
The image presents a chemical reaction where a secondary alkyl bromide is the starting material. This compound has a benzene ring attached to a carbon chain that includes a bromine (Br) substituent on a stereocenter. The reaction conditions are given as sodium ethoxide (NaOEt) in ethanol (EtOH), which suggests that it is likely an elimination reaction, possibly favoring an E2 mechanism due to the strong base provided by NaOEt.
**Structural Overview:**
- **Starting Material:**
- Benzene ring attached to a carbon chain with a bromine atom.
- The bromine is bonded to a chiral center.
- **Reagents:**
- NaOEt (Sodium ethoxide): A strong, non-bulky base.
- EtOH (Ethanol): Commonly acts as a solvent and can also participate as a nucleophile or base.
**Expected Reaction Mechanism:**
- The presence of a strong base (NaOEt) in the absence of a bulky substituent indicates that an E2 elimination is probable.
- In the E2 mechanism, the base abstracts a β-hydrogen, leading to the formation of a double bond and the elimination of the bromine as a leaving group.
**Predicted Products:**
- The major product is likely to be an alkene formed via the elimination of the hydrogen atom in the β-position to the leaving group (Br).
- The configuration of the double bond will depend on the stereochemistry of the starting material and the mechanism pathway, potentially yielding either a cis- or trans-alkene.
**Considerations:**
- If multiple β-hydrogens are present, regioselectivity (Zaitsev's rule) might favor the more substituted alkene as the major product.
- Additional stereoisomers might form as minor products, depending on the stereochemical configuration of the starting material.
By considering these factors, the specific structure of the major and minor products can be inferred based on the principles of stereochemistry and reaction mechanisms in organic chemistry.
Expert Solution

Step 1
This reaction is occurred by E1CB mechanism . In which first carboanion is formed and loss of leaving group by forming an alkene. AS Shown below:
Step by step
Solved in 2 steps with 1 images

Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you


Chemistry for Today: General, Organic, and Bioche…
Chemistry
ISBN:
9781305960060
Author:
Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:
Cengage Learning



Chemistry for Today: General, Organic, and Bioche…
Chemistry
ISBN:
9781305960060
Author:
Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:
Cengage Learning


Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning

Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning