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Chapter 17: Q50P (page 846)

Number the following compounds in order of increasing pKa value.

Short Answer

Expert verified

The pKa is used to indicate the acidic strength.We can define pKa as a negative log of Ka, as Ka is an acid dissociation constant. Lower the value of pKa, stronger is the acid, while on the other hand,if the pKa value is high it indicates that the acid is weak.

Step by step solution

01

Step-by-Step SolutionStep 1: pKa

The pKa is used to indicate the acidic strength.We can define pKa as a negative log of Ka, as Ka is an acid dissociation constant. Lower the value of pKa, stronger is the acid, while on the other hand,if the pKa value is high it indicates that the acid is weak.

02

Increasing order of pKa values of the compounds

Stronger acid has a lower pKa value. In the above compounds, hydrogen which is present between the two carbonyl groups is the most acidic and has the lowest pKa value. In the second compound, oxygen next to the carbonyl group decreases the acidic strength, and hence, it is less acidic than the first one.

Increasing order of pKa

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Most popular questions from this chapter

Question: Explain why the α-hydrogen of an N,N-disubstituted amide is less acidic (pKa= 30) than the α-hydrogen of an ester (pKa= 25).

Explain why alkylation of anα α -carbon works best if the alkyl halide used in the reaction is a primary alkyl halide, and why alkylation does not work at all if a tertiary alkyl halide is used.

The 1 H NMR chemical shifts of nitromethane, dinitromethane, and trinitromethane are at d 6.10, d 4.33, and d 7.52. Match each chemical shift with the compound. Explain how chemical shift correlates with pKa.

Indicate how the following compounds can be synthesized from cyclohexanone and any other necessary reagents:

Propose a mechanism for the following reaction:
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