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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

Why do cis-1-bromo-2-ethylcyclohexane and trans-1-bromo-2-ethylcyclohexane form different major products when they undergo an E2 reaction?

a. Which reacts faster in an E2 reaction: 3-bromocyclohexene or Bromo cyclohexane?

b. Which reacts faster in an E1 reaction?

What percentage of the reaction described in Problem 31 takes place by the E2 pathway when [HO-] = 0.0025 M?

Draw the structure of DDE.

What is the major elimination product obtained from the reaction of each of the following alkyl halides with hydroxide ions?
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