Check all of the boxes that apply to the manner of addition leading to the major product of the reaction shown. H₂ H CH3 1. Hg(OAc)2, H₂O H 2. NaBH4
Check all of the boxes that apply to the manner of addition leading to the major product of the reaction shown. H₂ H CH3 1. Hg(OAc)2, H₂O H 2. NaBH4
Chemistry
10th Edition
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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![**Reaction Mechanism Explanation**
Below is a transcription and explanation intended for educational purposes related to the given reaction involving the transformation of an alkene under specific conditions.
**Instructions:**
Check all of the boxes that apply to the manner of addition leading to the major product of the reaction shown.
**Reaction Diagram:**
- The starting material is an alkene with a methyl group (CH₃) on the carbon chain.
- The reagents used are:
1. Hg(OAc)₂ and H₂O
2. NaBH₄
**Options:**
1. □ The entire process is concerted from starting material to final product
2. □ This process involves a carbocation intermediate
3. □ Addition is syn- only
4. □ Addition is not selectively syn- or anti- (a mix results)
5. □ A Markovnikov product is observed
6. □ The anti-Markovnikov product is observed
7. □ The same thing adds to each side, so this is neither Markovnikov nor anti-Markovnikov
8. □ Addition is anti- only
**Explanation:**
The reaction involves oxymercuration-demercuration, a method used to add water (H₂O) across an alkene.
- *First Step (Oxymercuration):* Mercuric acetate [Hg(OAc)₂] and water add across the double bond without forming a free carbocation. This step prevents rearrangement and typically results in Markovnikov addition, where the OH group from water attaches to the more substituted carbon.
- *Second Step (Demercuration):* Sodium borohydride (NaBH₄) removes the mercury group and reduces it to yield the alcohol.
**Reactions Characteristics:**
- The reaction does not proceed through a carbocation intermediary.
- The addition generally follows Markovnikov’s rule.
- It is not exclusively syn or anti-addition; a mixture may result depending on specific reaction conditions.
This analysis reflects the fundamental characteristics of oxymercuration-demercuration as applied to the given alkene substrate.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F33bbbf0b-88bb-45b1-8754-8633f615d0a4%2F5c713c81-2f69-4d37-94d9-144b5e5d9414%2Ftxxfkku_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Reaction Mechanism Explanation**
Below is a transcription and explanation intended for educational purposes related to the given reaction involving the transformation of an alkene under specific conditions.
**Instructions:**
Check all of the boxes that apply to the manner of addition leading to the major product of the reaction shown.
**Reaction Diagram:**
- The starting material is an alkene with a methyl group (CH₃) on the carbon chain.
- The reagents used are:
1. Hg(OAc)₂ and H₂O
2. NaBH₄
**Options:**
1. □ The entire process is concerted from starting material to final product
2. □ This process involves a carbocation intermediate
3. □ Addition is syn- only
4. □ Addition is not selectively syn- or anti- (a mix results)
5. □ A Markovnikov product is observed
6. □ The anti-Markovnikov product is observed
7. □ The same thing adds to each side, so this is neither Markovnikov nor anti-Markovnikov
8. □ Addition is anti- only
**Explanation:**
The reaction involves oxymercuration-demercuration, a method used to add water (H₂O) across an alkene.
- *First Step (Oxymercuration):* Mercuric acetate [Hg(OAc)₂] and water add across the double bond without forming a free carbocation. This step prevents rearrangement and typically results in Markovnikov addition, where the OH group from water attaches to the more substituted carbon.
- *Second Step (Demercuration):* Sodium borohydride (NaBH₄) removes the mercury group and reduces it to yield the alcohol.
**Reactions Characteristics:**
- The reaction does not proceed through a carbocation intermediary.
- The addition generally follows Markovnikov’s rule.
- It is not exclusively syn or anti-addition; a mixture may result depending on specific reaction conditions.
This analysis reflects the fundamental characteristics of oxymercuration-demercuration as applied to the given alkene substrate.
Expert Solution
Step 1: Interpretation of given problem
Given reaction is oxymercuration demercuration reaction.
In this reaction alkene is treated with mercury(II) acetate, Hg(OAc)2, H2O and the product is treated with sodium borohydride to give alcohol as major product.
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