Nucleophilicity

BITSAT 2015 Online › Organic Chemistry questions › Nucleophilicity

Indicate which compound in each of the follpwing will react faster?

Neopentyl iodide or 1-iodopentane with CH₃OH

CH₃S^- or CH₃O^- with ethyl bromide in ethanol.

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2 Answers

Vivek @ Born this Way ·2012-03-07 21:29:05

CH₃S^- is a better nucleophile than RO^- and less stronger base.

In first case, since the medium is aqueous ethanol, so at mild temperatures (i.e., 28-30 degrees), you would expect the SN1 Reaction to give the major product. (The minor product will come by E1). And thereby the compound forming the most stable carbocation will react faster. Hence Neo pentyl Iodide will react faster.