A) 17. What compound is the expected product upon hydrohalogenation with HBr of the alkene shown below? Br. B) -Br Br Br. E) -Br

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
**Question 17:**

What compound is the expected product upon hydrohalogenation with HBr of the alkene shown below?

**Alkene Provided:**

- Structure: A five-carbon chain with a double bond between the second and third carbon atoms from the left. The chain also has a methyl group attached to the third carbon atom (counting from the left). 

**Possible Products:**

- **A)** A structure where the Br is attached to the third carbon of a straight five-carbon chain, creating a secondary carbon with Br and a methyl group also attached at the same carbon.
  
- **B)** A structure where the Br is attached to the fourth carbon of a five-carbon chain, at the end of the chain, creating a primary carbon with Br.
  
- **C)** A structure where the Br is attached to the third carbon in a five-carbon chain between the second and fourth carbon atoms, creating a secondary carbon with Br.
  
- **D)** A structure where the Br is attached to the first carbon of a five-carbon chain.
  
- **E)** A structure where the Br is attached to the fifth carbon, at the end of the five-carbon chain.

**Explanation:**

- The question involves hydrohalogenation, which is the addition of hydrogen halides like HBr to an alkene. The bromine typically adds to the more substituted carbon of the double bond following Markovnikov's rule unless conditions specify otherwise. Consider the most stable carbocation intermediate for identifying the correct product.
Transcribed Image Text:**Question 17:** What compound is the expected product upon hydrohalogenation with HBr of the alkene shown below? **Alkene Provided:** - Structure: A five-carbon chain with a double bond between the second and third carbon atoms from the left. The chain also has a methyl group attached to the third carbon atom (counting from the left). **Possible Products:** - **A)** A structure where the Br is attached to the third carbon of a straight five-carbon chain, creating a secondary carbon with Br and a methyl group also attached at the same carbon. - **B)** A structure where the Br is attached to the fourth carbon of a five-carbon chain, at the end of the chain, creating a primary carbon with Br. - **C)** A structure where the Br is attached to the third carbon in a five-carbon chain between the second and fourth carbon atoms, creating a secondary carbon with Br. - **D)** A structure where the Br is attached to the first carbon of a five-carbon chain. - **E)** A structure where the Br is attached to the fifth carbon, at the end of the five-carbon chain. **Explanation:** - The question involves hydrohalogenation, which is the addition of hydrogen halides like HBr to an alkene. The bromine typically adds to the more substituted carbon of the double bond following Markovnikov's rule unless conditions specify otherwise. Consider the most stable carbocation intermediate for identifying the correct product.
Expert Solution
steps

Step by step

Solved in 3 steps with 3 images

Blurred answer
Knowledge Booster
Designing a Synthesis
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