Chapter 16: Ethers, Epoxides and Sulfides |
Cleavage of Ethers by HI or HBr
Reaction type: Nucleophilic Substitution
Summary
QUESTIONS
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Related reactions
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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. |
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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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© Dr. Ian Hunt, Department of Chemistry |