In protic solvents the naphthoxide ion (I) is alkylated primarily at position 1 (C-alkylation) whereas in polar

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In protic solvents the naphthoxide ion (I) is alkylated primarily at position 1 (C-alkylation) whereas in polar aprotic solvents, such as DMF, the product is almost exclusively the result of a conventional Williamson ether synthesis (O-alkylation):

Why does the change in solvent make a difference?

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Organic Chemistry

ISBN: 978-1118133576

11th edition

Authors: Graham Solomons, Craig Fryhle, Scott Snyder

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Question Posted: Apr 19, 2016 09:30 AM

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In protic solvents the naphthoxide ion (I) is alkylated primarily at position 1 (C-alkylation) whereas in polar

Question:

OH RBr protic solvent RBr DMF

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There are alternative representations for I namely Thus I is an ambident nucleophile Oalkyla...View the full answer

Organic Chemistry

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