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Show how you would make the following ethers, using only

Chapter 24, Problem 29SP

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QUESTION:

Problem 29SP

Show how you would make the following ethers, using only simple alcohols and any needed reagents as your starting materials.

(a) 1-methoxybutane

(b) 2-ethoxy-2-methylpropane

(c) benzyl cyclopentyl ether

(d) trans-2-methoxycyclohexanol

(e) the TIPS ether of (d)

(f) cyclohexyl cyclopentyl ether

Questions & Answers

QUESTION:

Problem 29SP

Show how you would make the following ethers, using only simple alcohols and any needed reagents as your starting materials.

(a) 1-methoxybutane

(b) 2-ethoxy-2-methylpropane

(c) benzyl cyclopentyl ether

(d) trans-2-methoxycyclohexanol

(e) the TIPS ether of (d)

(f) cyclohexyl cyclopentyl ether

ANSWER:

Solution:

Here we have to write the synthesis of following ethers:-

Step 1

(a) Synthesis of  1-methoxybutane

1-methoxybutane can be prepared from butan-ol. In this reaction butanol in presence of metallic sodium forms an intermediate product, which on addition with methyl bromide gives   1-methoxybutane with sodium bromide.  

 + NaBr

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