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Chapter 19: Q37 (page 758)

Which compound in each pair has the lower pKa? Which compound in each pair has the stronger conjugate base?

a.

b.

Short Answer

Expert verified

a.

Compound 2 has lower pKa and compound 1 has a stronger conjugate base.

b.

Compound 1 has lower pKa and compound 2 has a stronger conjugate base.

Step by step solution

01

pKa and acid strength

Strong acids have lower pKa,while weak acids have higher pKa values.

The presence of electron-withdrawing groups on a compound increases its acidity.

02

Conjugate base

The removal of a proton from a compound generates its conjugate base.

Stronger the acid, weaker is its conjugate base.

03

Comparing the acidity of the given compounds 

a.

Compounds in a

Compound 2 is more acidic as it contains the electron-withdrawing chlorine atom, and hence it will have lower pKa.

Since compound 1 is a weak acid, its conjugate base will be stronger.

b.

Compounds in b

Compound 1 is more acidic as it contains the electron-withdrawing cyanide (CN) group.

Since compound 2 is a weak acid, its conjugate base will be stronger.

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Most popular questions from this chapter

Question: Rank the following compounds in order of increasing boiling point.

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