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...
Related questions
Question
Which mechanism does the reaction proceed?
| a = Proton transfer | d = Radical chain addition | g = E2 Elimination |
| b = Lewis acid/base | e = Electrophilic addition | h = SN1 Nucleophilic substitution |
| c = Radical chain substitution | f = E1 Elimination | i = SN2 Nucleophilic substitution |
Transcribed Image Text:This image depicts a chemical reaction involving a nucleophilic addition to an epoxide.
**Reactants:**
1. **Epoxide:** The structure on the left is a three-membered cyclic ether, known as an epoxide. It consists of an oxygen atom bonded to two carbon atoms, forming a triangular structure.
2. **Sodium cyanide (NaCN):** This compound is depicted with the sodium (Na) ion and the cyanide (CN) ion.
**Reaction Conditions:**
- The solvent used is DMF (Dimethylformamide), which is often used in nucleophilic substitution reactions because of its polar aprotic nature.
**Product:**
- The product is a molecule where the epoxide ring has been opened. The CN group has bonded to one carbon atom of the original epoxide, and the OH group is on the adjacent carbon, leading to a structure with the following groups:
- On the left: a CN (cyanide) group attached to a carbon.
- On the bottom: a methyl group (CH₃) bonded to the same carbon with the CN group.
- On the right: an OH (hydroxyl) group bonded to the second carbon.
- On the top: another methyl group (CH₃) attached to the second carbon.
This process illustrates a typical ring-opening reaction with a nucleophile (cyanide ion) attacking the less hindered carbon of an epoxide, leading to the formation of a beta-hydroxy nitrile.
![### Chemical Reaction Involving Cyclohexylamine
**Reactants:**
- **Cyclohexylamine (\(C_6H_{11}NH_2\))**: A cyclic amine compound, consisting of a six-membered carbon ring with an amine group attached.
- **Excess Methyl Iodide (\(CH_3I\))**: An alkyl halide with one iodine atom.
**Reaction:**
Cyclohexylamine reacts with excess methyl iodide.
**Products:**
- **N,N,N-Trimethylcyclohexylammonium Iodide (\([C_6H_{11}N(CH_3)_3]^+ I^-\))**: A quaternary ammonium salt, where the nitrogen atom of cyclohexylamine now carries three methyl groups, resulting in a positively charged nitrogen with an iodide counterion.
- **Hydrogen Iodide (HI)**: A byproduct of the reaction.
The diagram details a nucleophilic substitution reaction where the amine group undergoes exhaustive methylation to form a quaternary ammonium salt. This is a common reaction pathway for transforming amines into more reactive quaternary ammonium compounds, often used in phase transfer catalysis or as antimicrobial agents.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F256c4f3d-afa6-47b8-bd7d-949ffd48af47%2F60e7c987-94bf-49fe-9449-0aee1937765e%2F1jz65f_processed.gif&w=3840&q=75)
Transcribed Image Text:### Chemical Reaction Involving Cyclohexylamine
**Reactants:**
- **Cyclohexylamine (\(C_6H_{11}NH_2\))**: A cyclic amine compound, consisting of a six-membered carbon ring with an amine group attached.
- **Excess Methyl Iodide (\(CH_3I\))**: An alkyl halide with one iodine atom.
**Reaction:**
Cyclohexylamine reacts with excess methyl iodide.
**Products:**
- **N,N,N-Trimethylcyclohexylammonium Iodide (\([C_6H_{11}N(CH_3)_3]^+ I^-\))**: A quaternary ammonium salt, where the nitrogen atom of cyclohexylamine now carries three methyl groups, resulting in a positively charged nitrogen with an iodide counterion.
- **Hydrogen Iodide (HI)**: A byproduct of the reaction.
The diagram details a nucleophilic substitution reaction where the amine group undergoes exhaustive methylation to form a quaternary ammonium salt. This is a common reaction pathway for transforming amines into more reactive quaternary ammonium compounds, often used in phase transfer catalysis or as antimicrobial agents.
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1) SN2 nucleophilic substitution ( Option - i)
2) SN2 nucleophilic substitution (Option- i)
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