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Write the reactions of Williamson of 2-e...

Write the reactions of Williamson of 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol.

Text Solution

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In the Willimison's synthesis, the reactants are alkyl halide and sodium salt of an alcoho. In order to avaid the formation fo alkene during the reactions the alkyl halide should be primary while sodium salt must be of branched chain alcohol. In the present case, alkyl halide must be derived from ethanol upon heating with halogen acid (e.g., HBr)
` CH_(3)underset("Ethanol")(CH_(2))OH+HBroverset("Heat")rarrCH_(3)underset("Bromoethane")(CH_(2))Br+H_(2)O`
Similary, the branched chain alcohol must react with sodium metal to form the corresponding sodium salt.
`{:(5" "4" "3" "2),(CH_(3)-CH_(2)-CH-CH-OH+NararrCH_(3)-CH_(2)-CH-CH-ONa+(1)/(2)H_(2)),(" "|" "|" "|" "|),(" "CH_(3)" "^(1)CH_(3)" "CH_(3)" "CH_(3)),(" "3-"Methylpentan-2-ol"" ""Sod-3-Methylpentan-2-o xide"):}`
The product of WIlliamson's synthesis is formed as a result of the following reaction :
`{:(" "5" "4" "3" "2),(CH_(3)-CH_(2)-CH-CH-ONa+BrCH_(2)CH_(3)rarrCH_(3)-CH_(2)-CH-CH-OCH_(2)CH_(3)+NaBr),(" "|" "|" "|" "|),(" "CH_(3)" "CH_(3)" "CH_(3)" """_(1)CH_(3)),(" 2-Etho xy-3-Methylpentane"):}`
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