OH HCl OTs KSH DMSO CH3 NaOCH3 CH3OH Br NaN3 Br ETOH/H20

Chemistry: Principles and Practice
3rd Edition
ISBN:9780534420123
Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Chapter22: Organic Chemistry And Biochemistry
Section: Chapter Questions
Problem 79QE
icon
Related questions
Question

Describe the predominant mechanism( SN1, E1, SN2, E2) in the following reaction to draw the major product(s). 

**Chemical Reaction Pathways**

1. **Reaction 1:**
   - **Starting Material:** A chiral alcohol with an alkene group.
   - **Reagent:** HCl (Hydrochloric acid)
   - **Reaction:** The hydroxyl group (OH) undergoes a substitution reaction with HCl. The exact product is not shown, but typically, an alkyl chloride would be formed.

2. **Reaction 2:**
   - **Starting Material:** A chiral tosylate (OTs) compound with an alkane chain.
   - **Reagents:** KSH (Potassium hydrosulfide) and DMSO (Dimethyl sulfoxide)
   - **Reaction:** The tosylate (OTs) group is replaced by a thiol (SH) group under these conditions, facilitating a nucleophilic substitution.

3. **Reaction 3:**
   - **Starting Material:** A chiral bromocyclohexane with a methyl group.
   - **Reagents:** NaOCH₃ (Sodium methoxide) in CH₃OH (Methanol)
   - **Reaction:** The bromine (Br) is replaced by an alkoxide (OCH₃) group, indicating a nucleophilic substitution reaction.

4. **Reaction 4:**
   - **Starting Material:** A bromoalkyl benzene derivative.
   - **Reagents:** NaN₃ (Sodium azide) in a mixture of EtOH (Ethanol) and H₂O (Water)
   - **Reaction:** The bromine group is substituted by an azide group (N₃), a common transformation in organic synthesis.

These reactions represent various examples of nucleophilic substitution reactions, where one nucleophile substitutes another within an organic molecule, often changing functional groups and influencing stereochemistry.
Transcribed Image Text:**Chemical Reaction Pathways** 1. **Reaction 1:** - **Starting Material:** A chiral alcohol with an alkene group. - **Reagent:** HCl (Hydrochloric acid) - **Reaction:** The hydroxyl group (OH) undergoes a substitution reaction with HCl. The exact product is not shown, but typically, an alkyl chloride would be formed. 2. **Reaction 2:** - **Starting Material:** A chiral tosylate (OTs) compound with an alkane chain. - **Reagents:** KSH (Potassium hydrosulfide) and DMSO (Dimethyl sulfoxide) - **Reaction:** The tosylate (OTs) group is replaced by a thiol (SH) group under these conditions, facilitating a nucleophilic substitution. 3. **Reaction 3:** - **Starting Material:** A chiral bromocyclohexane with a methyl group. - **Reagents:** NaOCH₃ (Sodium methoxide) in CH₃OH (Methanol) - **Reaction:** The bromine (Br) is replaced by an alkoxide (OCH₃) group, indicating a nucleophilic substitution reaction. 4. **Reaction 4:** - **Starting Material:** A bromoalkyl benzene derivative. - **Reagents:** NaN₃ (Sodium azide) in a mixture of EtOH (Ethanol) and H₂O (Water) - **Reaction:** The bromine group is substituted by an azide group (N₃), a common transformation in organic synthesis. These reactions represent various examples of nucleophilic substitution reactions, where one nucleophile substitutes another within an organic molecule, often changing functional groups and influencing stereochemistry.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 1 images

Blurred answer
Knowledge Booster
Protection of Groups in Organic 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
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry: Principles and Practice
Chemistry: Principles and Practice
Chemistry
ISBN:
9780534420123
Author:
Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry: An Atoms First Approach
Chemistry: An Atoms First Approach
Chemistry
ISBN:
9781305079243
Author:
Steven S. Zumdahl, Susan A. Zumdahl
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781133611097
Author:
Steven S. Zumdahl
Publisher:
Cengage Learning
Chemistry In Focus
Chemistry In Focus
Chemistry
ISBN:
9781337399692
Author:
Tro, Nivaldo J.
Publisher:
Cengage Learning,