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PROBLEM 7.49

Expert-verified
Organic Chemistry
Found in: Page 291

Short Answer

Question: Which of the following nucleophilic substitution reactions will take place?

a.

b.

ANSWER

a.

b.

See the step by step solution

Step by Step Solution

Leaving group ability

The leaving group is the one that readily takes up the electrons when a bond is broken. So, it is a weak Lewis base and should have a low pKa values.

Explanation of (a)

a. In this reaction, the leaving group in the substrate molecule is NH2- . The nucleophile is an iodide ion. But NH2- is a poor leaving group and its conjugate acid NH3 has a value pKa of 35. So, this reaction is not feasible easily.

Explanation of (b)

b. In this reaction, the leaving group in the substrate molecule is I-. The nucleophile is a methoxide ion. The iodide ion is one of the best leaving groups, and its conjugate acid has pKa value of -9. So, this reaction is feasible easily.

Thus, the answer is option (b).

Nucleophilic substitution reaction

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