Using the reagents listed in the table below, devise routes for the following transformations: OH 3-5-0 SH Br Specify the reagents you would use to carry out the conversion by using letters from the table. If two or more ways of conversion to the same product are possible, show only one of them.) a. NBS, heat b. H3PO4, heat c. H₂O / H₂SO4 d. PCC Reagents available e. NaNH, / NH3 f. H₂ CrO4 9. HIO4 h. H₂ / Lindlar catalyst i. H₂O j. CH3OH k. OsO4 / H₂O2 I. 1. BH3 2. H₂O2, NaOH, H₂O

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
**Transformation Task:**

Devise routes for the transformation of bromocyclopentane to cyclopentanol and then to cyclopentene using the provided reagents.

**Reaction Scheme:**

- Starting compound: Cyclopentane with a bromine substituent (Br)
- Intermediate: Cyclopentanol (OH)
- Final product: Cyclopentene

**Reagents Available:**

a. NBS, heat  
b. H₃PO₄, heat  
c. H₂O / H₂SO₄  
d. PCC  
e. NaNH₂ / NH₃  
f. H₂CrO₄  
g. HIO₄  
h. H₂ / Lindlar catalyst  
i. H₂O  
j. CH₃OH  
k. OsO₄ / H₂O₂  
l. 1. BH₃  2. H₂O₂, NaOH, H₂O  

**Instructions:**

Specify the reagents you would use to carry out the conversion using the letters from the table. If there are multiple routes to the same product, show only one.

**Reaction Steps:**

- **Step 1:** Convert bromocyclopentane to cyclopentanol.
- **Step 2:** Convert cyclopentanol to cyclopentene.

**Enter the reagents (in order of use):**

- **Step 1:** 
- **Step 2:** 

This exercise involves understanding the mechanisms required to achieve each transformation and selecting the correct reagents.
Transcribed Image Text:**Transformation Task:** Devise routes for the transformation of bromocyclopentane to cyclopentanol and then to cyclopentene using the provided reagents. **Reaction Scheme:** - Starting compound: Cyclopentane with a bromine substituent (Br) - Intermediate: Cyclopentanol (OH) - Final product: Cyclopentene **Reagents Available:** a. NBS, heat b. H₃PO₄, heat c. H₂O / H₂SO₄ d. PCC e. NaNH₂ / NH₃ f. H₂CrO₄ g. HIO₄ h. H₂ / Lindlar catalyst i. H₂O j. CH₃OH k. OsO₄ / H₂O₂ l. 1. BH₃ 2. H₂O₂, NaOH, H₂O **Instructions:** Specify the reagents you would use to carry out the conversion using the letters from the table. If there are multiple routes to the same product, show only one. **Reaction Steps:** - **Step 1:** Convert bromocyclopentane to cyclopentanol. - **Step 2:** Convert cyclopentanol to cyclopentene. **Enter the reagents (in order of use):** - **Step 1:** - **Step 2:** This exercise involves understanding the mechanisms required to achieve each transformation and selecting the correct reagents.
Expert Solution
steps

Step by step

Solved in 3 steps with 3 images

Blurred answer
Knowledge Booster
IR Spectroscopy of Organic Molecules
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