Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
Bartleby Related Questions Icon

Related questions

Question
2. Draw the products of the reactions below, making sure to specify stereochemistry where applicable.
expand button
Transcribed Image Text:2. Draw the products of the reactions below, making sure to specify stereochemistry where applicable.
### Reaction Pathways of Cyclopentene

This image depicts various chemical reactions of cyclopentene, a five-membered carbon ring with a double bond.

1. **Reaction with Br₂ (Bromine)**
   - When cyclopentene is treated with bromine (\( \text{Br}_2 \)), halogenation occurs. This reaction typically results in the addition of bromine atoms across the double bond, converting it into a dibromide.

2. **Osmylation with \( \text{OsO}_4 \)(Cat.), NMO**
   - Osmium tetroxide (\( \text{OsO}_4 \)), in the presence of a catalytic amount, with N-Methylmorpholine N-oxide (NMO), results in the dihydroxylation of the alkene. This adds OH groups across the double bond of cyclopentene, forming a vicinal diol.

3. **Bromine in Water (\( \text{Br}_2, \text{H}_2\text{O} \))**
   - Treating cyclopentene with bromine in the presence of water leads to bromohydrin formation. One bromine atom and one hydroxyl group are added across the double bond.

4. **Epoxidation and Hydrolysis**
   - Using m-CPBA (meta-Chloroperoxybenzoic acid):
     1. Epoxidation step forms an epoxide from the alkene.
     2. Subsequent hydrolysis with water in acidic conditions results in the opening of the epoxide ring to give a diol.

This schematic helps illustrate the range of transformations possible with cyclopentene, showcasing its reactivity with different reagents and highlighting the versatile nature of alkene chemistry.
expand button
Transcribed Image Text:### Reaction Pathways of Cyclopentene This image depicts various chemical reactions of cyclopentene, a five-membered carbon ring with a double bond. 1. **Reaction with Br₂ (Bromine)** - When cyclopentene is treated with bromine (\( \text{Br}_2 \)), halogenation occurs. This reaction typically results in the addition of bromine atoms across the double bond, converting it into a dibromide. 2. **Osmylation with \( \text{OsO}_4 \)(Cat.), NMO** - Osmium tetroxide (\( \text{OsO}_4 \)), in the presence of a catalytic amount, with N-Methylmorpholine N-oxide (NMO), results in the dihydroxylation of the alkene. This adds OH groups across the double bond of cyclopentene, forming a vicinal diol. 3. **Bromine in Water (\( \text{Br}_2, \text{H}_2\text{O} \))** - Treating cyclopentene with bromine in the presence of water leads to bromohydrin formation. One bromine atom and one hydroxyl group are added across the double bond. 4. **Epoxidation and Hydrolysis** - Using m-CPBA (meta-Chloroperoxybenzoic acid): 1. Epoxidation step forms an epoxide from the alkene. 2. Subsequent hydrolysis with water in acidic conditions results in the opening of the epoxide ring to give a diol. This schematic helps illustrate the range of transformations possible with cyclopentene, showcasing its reactivity with different reagents and highlighting the versatile nature of alkene chemistry.
Expert Solution
Check Mark
Knowledge Booster
Background pattern image
Chemistry
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
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY