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Chapter 15: Problem 24

Using your old and new roadmaps as a guide, show how to convert 1-propanol and diiodomethane into racemic trans-1-methyl-2-propylcyclopropane. You must use 1-propanol and diiodomethane as the source of all carbon atoms in the target molecule. Show all molecules synthesized along the way. (racemic)

Short Answer

Expert verified
Question: Describe the synthetic pathway to convert 1-propanol and diiodomethane into racemic trans-1-methyl-2-propylcyclopropane. Answer: The synthetic pathway involves three steps: 1) Convert 1-propanol to 1-bromopropane using HBr in a nucleophilic substitution reaction. 2) Combine 1-bromopropane and diiodomethane using a palladium-catalyzed Negishi coupling reaction to form 1-iodo-2-propylpropane. 3) Create the cyclopropane ring by treating 1-iodo-2-propylpropane with n-butyllithium (n-BuLi), forming racemic trans-1-methyl-2-propylcyclopropane.

Step by step solution

01

Convert 1-propanol to alkyl halide

In order to create our target molecule, we need to first convert 1-propanol (which is an alcohol) into an alkyl halide. This can be achieved using a simple nucleophilic substitution reaction. We can treat 1-propanol with HBr (hydrobromic acid), and the bromine ion will replace the hydroxyl group, yielding 1-bromopropane : 1-propanol + HBr → 1-bromopropane + H2O
02

Combine 1-bromopropane and diiodomethane

In this step, we will react the alkyl halide (1-bromopropane) with diiodomethane to form a new alkyl-alkyl bond. We can use a palladium-catalyzed coupling reaction, specifically, the Negishi coupling for this purpose. This reaction involves reacting the alkyl bromide and alkyl iodide in the presence of a palladium catalyst, zinc, and a suitable base. 1-bromopropane + diiodomethane + Zn + Pd(0) + base → 1-iodo-2-propylpropane + iodine
03

Create the cyclopropane ring

Now that we have the necessary linear carbon chain, our next step is to form the cyclopropane ring. The 1-iodo-2-propylpropane can be treated with a base such as n-butyllithium (n-BuLi), which will deprotonate the alkyl chain and create a carbanion that can attack the iodine atom, leading to a three-membered cyclopropane ring: 1-iodo-2-propylpropane + n-BuLi → trans-1-methyl-2-propylcyclopropane And there you have it! The racemic trans-1-methyl-2-propylcyclopropane has been formed through a multi-step synthesis using 1-propanol and diiodomethane as the carbon sources.

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