H₂C H₂C- H₂C Br CH₂ Br CH₂ R-Me, Et. -Butyl H₂C Br+ MR-O +MR-O +MR-O M-K for RHButyl. M-Na for R-Me. Et

Chemistry
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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
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**Educational Website Transcription**

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**Abstract:**

This experiment compares product distribution from alkyl bromides using substitution or elimination reactions with various bases. The influence of the base and substrate on product distribution is studied with a focus on the outcome for olefin and ether products. The experiment is designed for second-year undergraduate chemistry students to understand these reactions better. Techniques like gas chromatography are key for the analysis, illustrating the composition and yield of the reactions.

**Keywords:**

- Second-Year Undergraduate
- Analytical Chemistry
- Laboratory Instruction
- Organic Chemistry
- Hands-On Learning
- Manipulatives
- Inquiry-Based/Discovery Learning
- Elimination Reactions
- Gas Chromatography
- Nucleophilic Substitution

**Introduction:**

The substitution and elimination reactions are vital for organic chemistry curricula but can be challenging to learn. This experiment reviews the impact of nucleophiles, solvents, and substrates on these reactions, with a practical method for analyzing product distributions using gas chromatography.

**Graph Explanation:**

- The presented graph shows the distribution of olefin (green bars) and ether (red bars) products for different reagents, highlighting the variation caused by different reactions.

**Experiment Details:**

**Scheme 1: Overall Reactions**

The reactions involve the substitution of bromine in alkyl bromides with nucleophiles (M⁺ R-O⁻) leading to different products based on the structure of the reagent, indicated by substituents like H₃C, CH₃, and others.

**Table 1: Reagents**

A list of reagents is detailed with molarity, molar mass, and respective volumes needed for the experiment, including:

- 1-Bromopentane
- 2-Bromopentane
- 2-Bromo-2-methylpentane
- Sodium methoxide and ethoxide in methanol or ethanol
- Sodium hydroxide and tert-butoxide in methanol
- Ammonium chloride

**Figure 1 & 2: Gas Chromatography (GC) Results**

- **Figure 1:** GC analysis of products from the reaction of 2-bromopentane and sodium ethoxide in ethanol. Peaks represent different reaction products with retention times.

- **Figure 2:** GC analysis for 1-bromopentane shows a range of components reflecting the distinct distribution due to its structural difference.

The experiment, taking 15–20 minutes, offers hands
Transcribed Image Text:**Educational Website Transcription** --- **Abstract:** This experiment compares product distribution from alkyl bromides using substitution or elimination reactions with various bases. The influence of the base and substrate on product distribution is studied with a focus on the outcome for olefin and ether products. The experiment is designed for second-year undergraduate chemistry students to understand these reactions better. Techniques like gas chromatography are key for the analysis, illustrating the composition and yield of the reactions. **Keywords:** - Second-Year Undergraduate - Analytical Chemistry - Laboratory Instruction - Organic Chemistry - Hands-On Learning - Manipulatives - Inquiry-Based/Discovery Learning - Elimination Reactions - Gas Chromatography - Nucleophilic Substitution **Introduction:** The substitution and elimination reactions are vital for organic chemistry curricula but can be challenging to learn. This experiment reviews the impact of nucleophiles, solvents, and substrates on these reactions, with a practical method for analyzing product distributions using gas chromatography. **Graph Explanation:** - The presented graph shows the distribution of olefin (green bars) and ether (red bars) products for different reagents, highlighting the variation caused by different reactions. **Experiment Details:** **Scheme 1: Overall Reactions** The reactions involve the substitution of bromine in alkyl bromides with nucleophiles (M⁺ R-O⁻) leading to different products based on the structure of the reagent, indicated by substituents like H₃C, CH₃, and others. **Table 1: Reagents** A list of reagents is detailed with molarity, molar mass, and respective volumes needed for the experiment, including: - 1-Bromopentane - 2-Bromopentane - 2-Bromo-2-methylpentane - Sodium methoxide and ethoxide in methanol or ethanol - Sodium hydroxide and tert-butoxide in methanol - Ammonium chloride **Figure 1 & 2: Gas Chromatography (GC) Results** - **Figure 1:** GC analysis of products from the reaction of 2-bromopentane and sodium ethoxide in ethanol. Peaks represent different reaction products with retention times. - **Figure 2:** GC analysis for 1-bromopentane shows a range of components reflecting the distinct distribution due to its structural difference. The experiment, taking 15–20 minutes, offers hands
**Exercise 1: Alkyl Halides and Nucleophiles/Bases**

*Task:*

1. Name and draw structures of the alkyl halides and nucleophiles/bases used below.

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*Instructions:*

- Identify the given alkyl halides and nucleophiles/bases.
- Provide a clear diagram of their molecular structures.
- Ensure each component is correctly labeled to facilitate learning.

*Notes:*

- **Alkyl halides** are compounds in which a halogen atom is bonded to an alkyl group, typically found in organic chemistry.
- **Nucleophiles and bases** are substances that donate an electron pair to form a chemical bond in a reaction.

*Objective:*

- To enhance understanding of organic compounds and reaction mechanisms.
Transcribed Image Text:**Exercise 1: Alkyl Halides and Nucleophiles/Bases** *Task:* 1. Name and draw structures of the alkyl halides and nucleophiles/bases used below. --- *Instructions:* - Identify the given alkyl halides and nucleophiles/bases. - Provide a clear diagram of their molecular structures. - Ensure each component is correctly labeled to facilitate learning. *Notes:* - **Alkyl halides** are compounds in which a halogen atom is bonded to an alkyl group, typically found in organic chemistry. - **Nucleophiles and bases** are substances that donate an electron pair to form a chemical bond in a reaction. *Objective:* - To enhance understanding of organic compounds and reaction mechanisms.
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