A mechanism for the reaction of bromine with 4,4-dimethylcyclopentene in water is shown below. Which of the following statements about this mechanism is correct? Step 1 Br Br Br + Br Br Step 2 Br OH2 OH2 Br Br OH2 Step 3 + Hо H OH O In Step 1, bromine could add to the other face of the alkene, giving a bromonium ion that is the enantiomer of the one shown. O In Step 2, water could attack the other carbon atom of the bromonium ion, leading to the enantiomer of the product shown. O This mechanism is complete and correct. O In Step 2, water could attack the bromonium ion from the other side, leading to the cis product.

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
**Mechanism for the Reaction of Bromine with 4,4-Dimethylcyclopentene in Water**

The mechanism involves the addition of bromine to 4,4-dimethylcyclopentene, resulting in different potential products depending on how bromine and water interact with the substrate. Below is a detailed description of the steps and a multiple-choice question related to the correctness of the mechanism.

**Step 1:**
- The reaction begins with the attack of the double bond in 4,4-dimethylcyclopentene on a bromine molecule (Br₂). 
- This results in the formation of a cyclic bromonium ion and the release of a bromide ion (Br⁻).
- The bromonium ion has a positive charge localized on the bromine atom.

**Step 2:**
- Water (H₂O) approaches and attacks the more substituted carbon atom of the bromonium ion, opening the three-membered ring.
- This reaction forms an intermediate with a hydroxyl group (OH) attached and a positively charged oxygen atom.

**Step 3:**
- A proton transfer occurs from the oxygen to a water molecule, resulting in the formation of a neutral alcohol and hydronium ion (H₃O⁺).

**Graph/Diagram Explanation:**
- The diagram shows the transformation from 4,4-dimethylcyclopentene to a bromonium ion, then to the intermediate, and finally to the end product, a bromohydrin, along with the generation of H₃O⁺.

**Multiple-choice question:**
- Which of the following statements about this mechanism is correct?

  - In Step 1, bromine could add to the other face of the alkene, giving a bromonium ion that is the enantiomer of the one shown.
  - In Step 2, water could attack the other carbon atom of the bromonium ion, leading to the enantiomer of the product shown.
  - This mechanism is complete and correct.
  - In Step 2, water could attack the bromonium ion from the other side, leading to the cis product.
Transcribed Image Text:**Mechanism for the Reaction of Bromine with 4,4-Dimethylcyclopentene in Water** The mechanism involves the addition of bromine to 4,4-dimethylcyclopentene, resulting in different potential products depending on how bromine and water interact with the substrate. Below is a detailed description of the steps and a multiple-choice question related to the correctness of the mechanism. **Step 1:** - The reaction begins with the attack of the double bond in 4,4-dimethylcyclopentene on a bromine molecule (Br₂). - This results in the formation of a cyclic bromonium ion and the release of a bromide ion (Br⁻). - The bromonium ion has a positive charge localized on the bromine atom. **Step 2:** - Water (H₂O) approaches and attacks the more substituted carbon atom of the bromonium ion, opening the three-membered ring. - This reaction forms an intermediate with a hydroxyl group (OH) attached and a positively charged oxygen atom. **Step 3:** - A proton transfer occurs from the oxygen to a water molecule, resulting in the formation of a neutral alcohol and hydronium ion (H₃O⁺). **Graph/Diagram Explanation:** - The diagram shows the transformation from 4,4-dimethylcyclopentene to a bromonium ion, then to the intermediate, and finally to the end product, a bromohydrin, along with the generation of H₃O⁺. **Multiple-choice question:** - Which of the following statements about this mechanism is correct? - In Step 1, bromine could add to the other face of the alkene, giving a bromonium ion that is the enantiomer of the one shown. - In Step 2, water could attack the other carbon atom of the bromonium ion, leading to the enantiomer of the product shown. - This mechanism is complete and correct. - In Step 2, water could attack the bromonium ion from the other side, leading to the cis product.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps

Blurred answer
Knowledge Booster
Selection Rules for Pericyclic Reactions
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.
Similar questions
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