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Chapter 11: Q 11-11-42 E-b (page 350)

Which reactant in each of the following pairs is more nucleophilic? Explain.

b) H2O or CH3CO2-

Short Answer

Expert verified

CH3CO2-

Step by step solution

01

Nucleophile

The nucleophiles are the negatively charged ions or the neutral species with the lone pair of electrons ready to bond.

02

Rules to identify more nucleophilic species

  1. Nucleophile attacking the same atom then nucleophilicity is same as basicity that more basic species is more nucleophilic.
  2. Nucleophilicity increases in going down in a periodic table group.
  3. A negatively charged nucleophile is more nucleophilic than a neutral nucleophile due to a negative charge.
03

More nucleophiles among H2O or CH3CO2-

Based on:

Rule 1: Nucleophile attacking the same atom then nucleophilicity is same as basicity that more basic species is more nucleophilic.

Rule3: A negatively charged nucleophile is more nucleophilic than a neutral nucleophile due to a negative charge.

CH3CO2-is more nucleophilic than H2O.

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Most popular questions from this chapter

Which reaction in each of the following pairs would you expect to be faster?

(a) TheSN2displacement byI- on CH3Cl or CH3OTs

Methyl esters (RCO2CH3) undergo a cleavage reaction to yield carboxylate ions plus iodomethane on heating with LiI in dimethylformamide:

The following evidence has been obtained: (1) The reaction occurs much faster in DMF than in ethanol. (2) The corresponding ethyl ester (RCO2CH2CH3) cleaves approximately 10 times more slowly than the methyl ester. Propose a mechanism for the reaction. What other kinds of experimental evidence could you gather to support your hypothesis?

What product would you expect to obtain from reaction of with (R)-2-bromobutane? Show the stereochemistry of both the reactant and product.

Rank the following compounds in order of their expected reactivity toward SN2reaction:

CH3Br,CH3OTos,CH33CCl,CH32CHCl

Which reaction in each of the following pairs would you expect to be faster?

(c) TheSN2displacement on 2-bromopropane by CH3CH2O-or byCN-
See all solutions

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