Nucleophilic Substitution IN ETHERS
- Alkyl ethers are cleaved by the strong acids HI or HBr in a nucleophilic substitution reaction similar to that of alcohols.
- Protonation of the ethereal oxygen creates a good leaving group, a neutral alcohol molecule.
- The halide ion, bromide or iodide are both good nucleophiles.
- Depending on the structure of the alkyl groups, the reaction can be SN1 or SN2 like.
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MECHANISM FOR ACID CLEAVAGE OF ETHERS |
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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