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The following compounds can all react as acids. CH3 C OH O CH3 C OOH CH3CH2 O CF3 C OH O

Chapter 2, Problem 2-45

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QUESTION:

The following compounds can all react as acids.

(a) For each compound, show its conjugate base. Show any resonance forms if applicable.

(b) Rank the conjugate bases in the order you would predict, from most stable to least stable.

(c) Rank the original compounds in order, from strongest acid to weakest acid.

Questions & Answers

QUESTION:

The following compounds can all react as acids.

(a) For each compound, show its conjugate base. Show any resonance forms if applicable.

(b) Rank the conjugate bases in the order you would predict, from most stable to least stable.

(c) Rank the original compounds in order, from strongest acid to weakest acid.

ANSWER:

Step 1 of 4

(a) The acetic acid loses its proton connected to the oxygen atom to form a conjugate base. The conjugate base and resonance forms are given as:

                                 

2,2,2 Trifluoroacetic acid has lost its proton to form the resonance stabilized anion. The resonance structure can be given as:

                                   

 

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