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Chapter 16: Ethers, Epoxides and Sulfides

Summary | Ethers | Preparations of Ethers | Reactions of Ethers | Epoxides | Preparation of Epoxides | Reactions of Epoxides | Spectroscopic Analysis of Ethers | Sulfides | Self Assessment | Quiz |

Reactions of  Ethers

Chapter 16: Ethers, Epoxides and Sulfides

Cleavage of Ethers by HI or HBr

acid cleavage of ethers
Reaction type: Nucleophilic Substitution


If excess HBr is used, what would the products of the reaction be ? 
Is the mechanism shown below SN1 or SN2 ? S<sub>N</sub>2 - no carbocation, Nu attacks as LG leaves

Related reactions

Step 1:
An acid/base reaction. Protonation of the alcoholic oxygen to make a better leaving group. This step is very fast and reversible.  The lone pairs on the oxygen make it a Lewis base.
HX ether cleaveage
Step 2:
The bromide ion functions as the nucleophile and attacks to displace the good leaving group, neutral alcohol molecule, by cleaving the C-O bond. This results in the formation of an alkyl bromide and an alcohol. 


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