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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 pK_a 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 pK_aof 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 pK_avalue 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: Draw the eight constitutional isomers having the molecular formula C₅H₁₁Cl .

Give the IUPAC name for each compound (ignoring R and S designations).
Classify each alkyl halide as $1 °, 2 ° o r 3 °$ .
Label any stereogenic centers.
For each constitutional isomer that contains a stereogenic center, draw all possible stereoisomers, and label each stereogenic center as R or S.

Question: What happens to the rate of an S_N1 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: (a) Rank A, B, and C in order of increasing S_N2 reactivity. (b) Rank A, B, and C in order of increasing S_N1 reactivity.

Question: Determine the mechanism of nucleophilic substitution of each reaction and draw the products, including stereochemistry.

a.

b.

c.

d.

e.

f.

Question: Which compound in each pair reacts faster in nucleophilic substitution?

a.

b.

c.

d.

See all solutions

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