shown, with the resulting major product being an internal alkyne? 1) NaNH2 2) R-Br Br Br Br Br Br II III IV V O Il and IV O I, II, IV II, IV, V O l and III O II, III, V

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
icon
Concept explainers
Question
### Organic Chemistry Question

#### Problem:
Which of the alkyl bromides listed would work as a reagent in step 2 of the reaction sequence shown, with the resulting major product being an internal alkyne?

#### Reaction Sequence Diagram:
The diagram presents a two-step reaction sequence:
1) The alkyne is treated with sodium amide (NaNH₂).
2) The resulting product is reacted with an alkyl bromide (R-Br).

#### Chemical Structures:
Five chemical structures labeled I to V are provided, each representing an alkyl bromide.

1. **Structure I**: Cyclopentyl bromide
2. **Structure II**: (3-Bromopropyl) methylethyl
3. **Structure III**: 2-Bromobutane
4. **Structure IV**: 1-Bromobutane
5. **Structure V**: Cyclohexyl bromide

#### Answer Options:
- ○ II and IV
- ○ I, II, IV
- ○ III, IV, V
- ○ I and III
- ○ II, III, V

#### Explanation:
To form an internal alkyne, the resulting product after reaction with the alkyl bromide should contain a carbon-carbon triple bond within the carbon chain, not at the terminal position.

#### Analysis of Options:
- **II and IV**: 
  - **II**: 3-Bromopropyl methylethyl
  - **IV**: 1-Bromobutane
- **I, II, IV**: 
  - **I**: Cyclopentyl bromide
  - **II**: 3-Bromopropyl methylethyl
  - **IV**: 1-Bromobutane
- **III, IV, V**: 
  - **III**: 2-Bromobutane
  - **IV**: 1-Bromobutane
  - **V**: Cyclohexyl bromide
- **I and III**: 
  - **I**: Cyclopentyl bromide
  - **III**: 2-Bromobutane
- **II, III, V**: 
  - **II**: 3-Bromopropyl methylethyl
  - **III**: 2-Bromobutane
  - **V**: Cyclohex
Transcribed Image Text:### Organic Chemistry Question #### Problem: Which of the alkyl bromides listed would work as a reagent in step 2 of the reaction sequence shown, with the resulting major product being an internal alkyne? #### Reaction Sequence Diagram: The diagram presents a two-step reaction sequence: 1) The alkyne is treated with sodium amide (NaNH₂). 2) The resulting product is reacted with an alkyl bromide (R-Br). #### Chemical Structures: Five chemical structures labeled I to V are provided, each representing an alkyl bromide. 1. **Structure I**: Cyclopentyl bromide 2. **Structure II**: (3-Bromopropyl) methylethyl 3. **Structure III**: 2-Bromobutane 4. **Structure IV**: 1-Bromobutane 5. **Structure V**: Cyclohexyl bromide #### Answer Options: - ○ II and IV - ○ I, II, IV - ○ III, IV, V - ○ I and III - ○ II, III, V #### Explanation: To form an internal alkyne, the resulting product after reaction with the alkyl bromide should contain a carbon-carbon triple bond within the carbon chain, not at the terminal position. #### Analysis of Options: - **II and IV**: - **II**: 3-Bromopropyl methylethyl - **IV**: 1-Bromobutane - **I, II, IV**: - **I**: Cyclopentyl bromide - **II**: 3-Bromopropyl methylethyl - **IV**: 1-Bromobutane - **III, IV, V**: - **III**: 2-Bromobutane - **IV**: 1-Bromobutane - **V**: Cyclohexyl bromide - **I and III**: - **I**: Cyclopentyl bromide - **III**: 2-Bromobutane - **II, III, V**: - **II**: 3-Bromopropyl methylethyl - **III**: 2-Bromobutane - **V**: Cyclohex
Expert Solution
steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Ethers
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