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Chapter 9: Problem 57

Using your roadmap as a guide, show how to convert 2-methylbutane into racemic 3-bromo-2-methyl-2-butanol. Show all reagents and all molecules synthesized along the way.

Short Answer

Expert verified
Question: Convert 2-methylbutane into racemic 3-bromo-2-methyl-2-butanol and show all reagents and molecules synthesized along the way. Answer: 1. Perform dehydrohalogenation of 2-methylbutane to form 2-methyl-2-butene using HCl, KOH, and ethanol. 2. Brominate 2-methyl-2-butene to form 2,3-dibromo-2-methylbutane with Br2. 3. Carry out a substitution reaction using water and NaOH to replace one bromine atom in 2,3-dibromo-2-methylbutane, forming racemic 3-bromo-2-methyl-2-butanol and NaBr.

Step by step solution

01

Dehydrohalogenation of 2-methylbutane to form 2-methyl-2-butene

To accomplish this, we first react 2-methylbutane with HCl to form 2-chloro-2-methylbutane, followed by dehydrohalogenation using a strong base. Reagents: HCl, KOH, and ethanol Reaction steps: 1. 2-methylbutane + HCl → 2-chloro-2-methylbutane 2. 2-chloro-2-methylbutane + KOH (in ethanol) → 2-methyl-2-butene + KCl
02

Bromination of 2-methyl-2-butene to form 2,3-dibromo-2-methylbutane

The next step is bromination of the double bond in 2-methyl-2-butene. We will use Br2 as a reagent for this purpose. Reagent: Br2 Reaction step: 1. 2-methyl-2-butene + Br2 → 2,3-dibromo-2-methylbutane
03

Substitution reaction to form racemic 3-bromo-2-methyl-2-butanol

In the final step, we perform a substitution reaction using water to replace one of the bromine atoms on the 2,3-dibromo-2-methylbutane. This will result in the formation of racemic 3-bromo-2-methyl-2-butanol. Reagents: H2O, NaOH Reaction steps: 1. 2,3-dibromo-2-methylbutane + H2O (in the presence of NaOH) → racemic 3-bromo-2-methyl-2-butanol + NaBr Now, we have successfully converted 2-methylbutane into racemic 3-bromo-2-methyl-2-butanol and showed all reagents and molecules synthesized along the way.

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