CH HCHS 2. NAEH,

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...
icon
Related questions
Question

Draw structural formulas for all alkenes that could be used to prepare the alcohol shown below by oxymercuration.

**Chemical Reaction Explanation: Oxymercuration-Demercuration**

The image depicts a chemical reaction that involves the conversion of an alkene to an alcohol using the oxymercuration-demercuration method. This reaction is generally characterized by the addition of water across the carbon-carbon double bond in an alkene to form an alcohol.

**Reactants and Reagents:**

1. **Starting Material (Alkene):** The question mark in the image signifies the missing starting material, which is an alkene. Given the alcohol product, the alkene likely has a double bond where the hydroxyl group (OH) is added.

2. **Reagents:**
   - **Step 1:** Hg(OAc)₂ (Mercuric acetate) and H₂O (Water) are used to form a mercurinium ion intermediate.
   - **Step 2:** NaBH₄ (Sodium borohydride) is used to reduce the intermediate, replacing the mercury group with a hydrogen atom.

**Product:**

The product displayed is an alcohol: 
- It has a hydroxyl group (CHOH) attached to a secondary carbon.
- The structure includes a methyl group (CH₃) and a lengthy alkyl chain (CH₃CH₂CH₂CH=CHCH₂CH₂CH₃).

**Mechanism Overview:**

1. **Oxymercuration:** The alkene reacts with mercuric acetate in the presence of water to form a cyclic mercurinium ion. Water attacks the more substituted carbon, leading to the formation of an organomercury intermediate.

2. **Demercuration:** Sodium borohydride reduces the organomercury intermediate, leading to the replacement of the mercury portion with a hydrogen atom and resulting in the formation of the alcohol product.

This reaction is useful for its Markovnikov selectivity, adding the OH group to the more substituted carbon of the double bond, without rearrangements that can occur in typical acid-catalyzed hydration.
Transcribed Image Text:**Chemical Reaction Explanation: Oxymercuration-Demercuration** The image depicts a chemical reaction that involves the conversion of an alkene to an alcohol using the oxymercuration-demercuration method. This reaction is generally characterized by the addition of water across the carbon-carbon double bond in an alkene to form an alcohol. **Reactants and Reagents:** 1. **Starting Material (Alkene):** The question mark in the image signifies the missing starting material, which is an alkene. Given the alcohol product, the alkene likely has a double bond where the hydroxyl group (OH) is added. 2. **Reagents:** - **Step 1:** Hg(OAc)₂ (Mercuric acetate) and H₂O (Water) are used to form a mercurinium ion intermediate. - **Step 2:** NaBH₄ (Sodium borohydride) is used to reduce the intermediate, replacing the mercury group with a hydrogen atom. **Product:** The product displayed is an alcohol: - It has a hydroxyl group (CHOH) attached to a secondary carbon. - The structure includes a methyl group (CH₃) and a lengthy alkyl chain (CH₃CH₂CH₂CH=CHCH₂CH₂CH₃). **Mechanism Overview:** 1. **Oxymercuration:** The alkene reacts with mercuric acetate in the presence of water to form a cyclic mercurinium ion. Water attacks the more substituted carbon, leading to the formation of an organomercury intermediate. 2. **Demercuration:** Sodium borohydride reduces the organomercury intermediate, leading to the replacement of the mercury portion with a hydrogen atom and resulting in the formation of the alcohol product. This reaction is useful for its Markovnikov selectivity, adding the OH group to the more substituted carbon of the double bond, without rearrangements that can occur in typical acid-catalyzed hydration.
Expert Solution
steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Alkanes and Cycloalkanes
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
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY