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

Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers.

**Transcription for Educational Website**

---

**Chemical Reaction Mechanisms**

**1. Reaction 1:**

\[
\text{(CH}_3\text{)_3COH + \text{conc. HCl} \rightarrow \text{(CH}_3\text{)_3CCl + H}_2\text{O}}
\]

In this reaction, tert-butyl alcohol reacts with concentrated hydrochloric acid to produce tert-butyl chloride and water.

**2. Reaction 2:**

\[
\text{(CH}_3\text{)_2C(=O)CH}_2\text{CH(OH)CH}_3 + \text{I}_2 \xrightarrow{\text{NaHCO}_3} \text{(CH}_3\text{)_2C(=O)CHI} + \text{H}_2\text{O + CO}_2 + \text{NaI}
\]

In this reaction, a cyclic ketone with an alcohol group reacts with iodine in the presence of sodium bicarbonate, forming an iodinated ketone, water, carbon dioxide, and sodium iodide.

**Mechanisms:**

a = Proton transfer  
b = Lewis acid/base  
c = Radical chain substitution  
d = Electrophilic addition  
e = E1 Elimination  
f = E2 Elimination  
g = S\(_N\)1 Nucleophilic substitution  
h = S\(_N\)2 Nucleophilic substitution  

**Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - h for your answers.**

1. [ ]  
2. [ ]

---

**Detailed Explanation of Diagrams:**

- **Diagram 1** illustrates the substitution of the hydroxyl group (OH) in tert-butyl alcohol by a chlorine atom (Cl) from hydrochloric acid, resulting in the formation of tert-butyl chloride and water as a byproduct.
- **Diagram 2** shows a ring structure where a ketone reacts with iodine, resulting in substitution on the alpha carbon adjacent to the carbonyl group, forming an iodinated cyclic compound along with the release of water, carbon dioxide, and sodium iodide. 

Remember, the identification of specific reaction mechanisms relies on understanding the substituent groups, reagents, and products, which can be predicted using known organic chemistry principles.
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Transcribed Image Text:**Transcription for Educational Website** --- **Chemical Reaction Mechanisms** **1. Reaction 1:** \[ \text{(CH}_3\text{)_3COH + \text{conc. HCl} \rightarrow \text{(CH}_3\text{)_3CCl + H}_2\text{O}} \] In this reaction, tert-butyl alcohol reacts with concentrated hydrochloric acid to produce tert-butyl chloride and water. **2. Reaction 2:** \[ \text{(CH}_3\text{)_2C(=O)CH}_2\text{CH(OH)CH}_3 + \text{I}_2 \xrightarrow{\text{NaHCO}_3} \text{(CH}_3\text{)_2C(=O)CHI} + \text{H}_2\text{O + CO}_2 + \text{NaI} \] In this reaction, a cyclic ketone with an alcohol group reacts with iodine in the presence of sodium bicarbonate, forming an iodinated ketone, water, carbon dioxide, and sodium iodide. **Mechanisms:** a = Proton transfer b = Lewis acid/base c = Radical chain substitution d = Electrophilic addition e = E1 Elimination f = E2 Elimination g = S\(_N\)1 Nucleophilic substitution h = S\(_N\)2 Nucleophilic substitution **Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - h for your answers.** 1. [ ] 2. [ ] --- **Detailed Explanation of Diagrams:** - **Diagram 1** illustrates the substitution of the hydroxyl group (OH) in tert-butyl alcohol by a chlorine atom (Cl) from hydrochloric acid, resulting in the formation of tert-butyl chloride and water as a byproduct. - **Diagram 2** shows a ring structure where a ketone reacts with iodine, resulting in substitution on the alpha carbon adjacent to the carbonyl group, forming an iodinated cyclic compound along with the release of water, carbon dioxide, and sodium iodide. Remember, the identification of specific reaction mechanisms relies on understanding the substituent groups, reagents, and products, which can be predicted using known organic chemistry principles.
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