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Chapter 11: Problem 44

Using your roadmap as a guide, show how to convert 1-butene into dibutyl ether. You must use 1-butene as the source of all carbon atoms in the dibutyl ether. Show all required reagents and all molecules synthesized along the way.

Short Answer

Expert verified
Question: Outline the synthesis of dibutyl ether starting from 1-butene. Include the intermediates and reagents used in each step. Answer: The synthesis of dibutyl ether from 1-butene involves the following steps: 1. Hydration of 1-butene using H2O/H2SO4 to form 2-butanol. 2. Nucleophilic substitution of 2-butanol with HBr to form 2-bromobutane. 3. Deprotonation of 2-butanol using NaH to form sodium 2-butoxide. 4. Williamson Ether synthesis, reacting sodium 2-butoxide with 2-bromobutane to form dibutyl ether and NaBr as a byproduct.

Step by step solution

01

1. Formation of Alcohol (Hydration of 1-butene)

To start with, we first need to convert 1-butene into an alcohol. This can be done by the reaction of 1-butene with water under acidic conditions (i.e., hydration reaction). The reagent used for this step is sulfuric acid and water (H2O/H2SO4). The hydration of 1-butene will yield 2-butanol. The reaction is as follows: 1-butene + H2O/H2SO4 -> 2-butanol
02

2. Conversion of Alcohol to the Corresponding Halide (Nucleophilic Substitution)

Next, we need to convert the 2-butanol into a suitable halide, such as 2-bromobutane. This can be achieved by reacting 2-butanol with hydrobromic acid (HBr). This is a nucleophilic substitution (SN2) reaction where the -OH group is replaced by the -Br group. The reaction is as follows: 2-butanol + HBr -> 2-bromobutane
03

3. Formation of the Sodioalkoxide (Alcohol Deprotonation)

In order to form an ether from the alcohol, we must first deprotonate the alcohol to form a sodioalkoxide. We can treat 2-butanol with a strong base like sodium hydride (NaH) to form sodium 2-butoxide. The reaction is as follows: 2-butanol + NaH -> sodium 2-butoxide (NaOBu)
04

4. Formation of Dibutyl Ether (Williamson Ether Synthesis)

Finally, we will use the Williamson Ether synthesis to form the dibutyl ether. This involves a nucleophilic attack by the sodioalkoxide (sodium 2-butoxide) on the 2-bromobutane formed in step 2. This leads to the formation of dibutyl ether and sodium bromide (NaBr) as a byproduct. The reaction is as follows: Sodium 2-butoxide + 2-bromobutane -> dibutyl ether + NaBr By following these steps, we have demonstrated the conversion of 1-butene into dibutyl ether using 1-butene as the source of carbon atoms while showing all the required reagents and molecules synthesized along the way.

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Most popular questions from this chapter

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