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Chapter 9: Q68P (page 451)

Which member of each pair is a better nucleophile in methanol?

a. H2O or HO-

b. NH3 or H2O

c. H2O or H2S

d. HO- or HS-

e. I- or Br-

f. Cl-or Br-

Short Answer

Expert verified
  1. HO-
  2. NH3
  3. H2S
  4. HS-
  5. I-
  6. Br-

Step by step solution

01

Definition

If the atoms are in the same horizontal row of the periodic table, the stronger base is the better nucleophile. If the atoms are in the same column, the larger the atom the better is the nucleophile in the protic polar solvent because the solvent will form stronger hydrogen bond with the smaller atom.

02

Final Answer

The member of each pair is a better nucleophile in methanol are as follows-

  1. HO-
  2. NH3
  3. H2S
  4. HS-
  5. I-
  6. Br-

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Most popular questions from this chapter

The reaction of chloromethane with hydroxide ion at 30掳C has a 螖G掳 value of -21.7 kcal/mol. What is the equilibrium constant for the reaction?

a. Propose a mechanism for the following reaction.

b. Explain why two products are formed.

c. Explain why methanol substitutes for only one of the bromines.

Explain why only a substitution product and no elimination product is obtained when the following Compound reacts with sodium methoxide:

What is the product of the reaction of bromoethane with each of the following nucleophiles?

Draw the substitution and elimination products for the following reactions, showing the configuration of each product:

a. trans-1-chloro-2-methylcyclohexane + CH3O-

b. cis-1-chloro-2-methylcyclohexane + CH3O鈭�

c. 1-chloro-1-methylcyclohexane + CH3O-

d. 1-chloro-1-methylcyclohexane + CH3OH
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