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Chapter 7: PROBLEM 7.49 (page 291)

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

a.

b.

Short Answer

Expert verified

ANSWER

a.

b.

Step by step solution

01

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.

02

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 pKaof 35. So, this reaction is not feasible easily.

03

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 pKavalue of -9. So, this reaction is feasible easily.

Thus, the answer is option (b).

Nucleophilic substitution reaction

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Most popular questions from this chapter

Question: What happens to the rate of an SN1 reaction under each of the following conditions?

a. [RX] is tripled, and :Nu-stays the same.

b. Both [RX] and :Nu-are tripled.

c. [RX] is halved, and :Nu-stays the same.

d. [RX] is halved, and:Nu-is doubled.

Question: Which compound in each pair has the higher boiling point?

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Question: Draw the structure of a 1掳,2掳,3掳, , carbocation, each having molecular formula . Rank the three carbocations in order of increasing stability.

Draw a stepwise mechanism for the following reaction that illustrates how two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under reaction conditions, even though it is a 1掳alkyl halide.

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