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
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.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fea03bc01-0c8f-4ac0-bde7-e545ccac1fc8%2Fd63fc23b-bf44-4074-a43a-21295d788ff6%2Filtgu_processed.jpeg&w=3840&q=75)
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.
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