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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: Classify each solvent as protic or aprotic.

  1. (CH3)2CHOH
  2. CH3NO2
  3. CH2Cl2
  4. NH3
  5. N(CH3)3
  6. HCONH2

Question: Fluticasone, the chapter-opening molecule, can be prepared by the following reaction. Draw a stepwise mechanism for this reaction.

Question: As you will learn in Chapter 9, the epoxide is an ether with an oxygen atom in a three-membered ring. Epoxides can be made by intramolecular SN2 reactions of intermediates that contain a nucleophile and a leaving group on adjacent carbons, as shown.

Assume that each of the following starting materials can be converted to an epoxide by this reaction. Draw the product formed (including stereochemistry) from each starting material. Why might some of these reactions be more difficult than others in yielding nucleophilic substitution products?

a.

b.

c.

d.

Question: Chondrocole A is a marine natural product isolated from red seaweed that grows in regions of heavy surf in the Pacific Ocean. (a) Predict the solubility of chondrocole A in water and . (b) Locate the stereogenic centers and label each as R or S. (c) Draw a stereoisomer and a constitutional isomer of chondrocole A.

Question: Draw an energy diagram for the following SN2 reaction. Label the axes, the starting materials, and the product. Draw the structure of the transition state.
See all solutions

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