Question

# 2-Pentanol can be converted to 2-ethoxy pentane by two paths. In path I, $$H^\oplus$$ is abstracted from 2-pentanol to form the nucleophile while in path II, $$H^\oplus$$ is abstracted from ethanol. What is true about the configuration at chiral $$C$$ of 2-pentanol?

A
Retained in both paths
B
Retained in path I and Inverted in path II
C
Inverted in path I and Retained in path I
D
Inverted in both paths

Solution

## The correct option is B Retained in path I and Inverted in path IIin path I, the nucleophile is $$C_3H_7\overset{\overset{\displaystyle O^\ominus}|}CHCH_3$$ ion. In path I, nucleophile has the chiral center and reaction takes place without breaking any bond, thus configuration in the final product is retained.In path II, nucleophile $$(C_2H_5O^{\circleddash})$$ attacks chiral centre back-side in an $$SN^2$$ reaction with inversion of configuration in ether.Chemistry

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