Question 44 - Chemical and Physical Foundations of Biological Systems Practice Test for the MCAT

Referring to the attachment, which of the following is the strongest nucleophile?

Nucleophilic substitution reactions are organic reactions in which an electron-rich substance called a nucleophile reacts with an organic substrate that has an electron-poor carbon atom called an electrophile.

The electrophile has a radical that is a weak base and is substituted by the nucleophile called the leaving group, hence the term nucleophilic substitution.

Nucleophilic substitution can occur via two different mechanisms: \(\text{SN}_1\), in which the rate determining step is the loss of the leaving group, and \(\text{SN}_2\), in which the rate-determining step is the nucleophilic attack and the simultaneous loss of the leaving group.

A scientist is studying the nucleophilic substitution reaction between 2-Bromopropane and a novel nucleophile (Nuc), collecting the kinetic data that is shown in the table below:

Trial \(N^o\) [2-Bromopropane]
Initial Rate
1 0.105 0.056 0.0378
2 0.320 0.056 0.1152
3 0.105 0.072 0.0378

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