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Chapter 2: 2.27 (page 78)

Which anion (A or B) is the stronger base?

Short Answer

Expert verified

B is the stronger base.

Step by step solution

01

Determination of strong organic bases

In organic chemistry, strong bases are determined based on the free lone pair of electrons.

If the adjacent lone pair of electrons does not undergo delocalization, the compound is a strong base.

02

Effect of lone pairs on basicity

In compound A, the oxide ion containing the lone pair of electrons shifts towards the electron-deficient carbonyl carbon (C=O). Due to this, the delocalization of lone pair of electrons on an oxygen atom occurs. Hence, A is not a strong base.

Conjugation of an oxide ion

In compound B, the oxide ion-containing lone pair of electrons are free to donate. Its electron-donating tendency is further enhanced by the cyclohexyl group. Hence, B is a strong base.

Therefore, B is a stronger base than A.

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Most popular questions from this chapter

Molecules like acetamide (CH3CONH2) can be protonated on either their O or N atoms when treated with a strong acid like HCl. Which site is more readily protonated and why?

What is the conjugate acid of each base?

a. HCO3-

b.

c.

d.

Label the acid and base and the conjugate acid and base in the following reactions. Use curved arrows to show the movement of electron pairs.

a.

b.

Classify each reaction as either a proton transfer reaction, or a reaction of a nucleophile with an electrophile. Use curved arrows to show how the electron pairs move.

Consider two acids:HCO2H (formic acid, pKa=3.8)and pivalic acid [CH3CCO2H,pKa=5.0].

(a)Which acid has the larger Ka? (b)Which acid is the stronger acid? (c) Which acid forms the stronger conjugate base?(d)When acid is dissolved in water, for which acid does the equilibrium lie further to the right?
See all solutions

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