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The following compounds are listed in increasing order of

Chapter 1, Problem 47SP

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QUESTION:

The following compounds are listed in increasing order of acidity. In each case, the most acidic proton is shown in red.

(a) Show the structure of the conjugate base of each acid, including any resonance forms.

(b) Explain why \(X\) is a stronger acid than \(W\)

(c) Explain why \(Y\) is a stronger acid than \(X\)

(d) Explain why \(Z\) is a stronger acid than \(Y\)

Equation Transcription:

Text Transcription:

CH_2

NH

OH

W,pKa=25

X,pKa=23

Y,pKa=8.8

Z,pKa=4.2

X

W

Y

X

Z

Y

Questions & Answers

QUESTION:

The following compounds are listed in increasing order of acidity. In each case, the most acidic proton is shown in red.

(a) Show the structure of the conjugate base of each acid, including any resonance forms.

(b) Explain why \(X\) is a stronger acid than \(W\)

(c) Explain why \(Y\) is a stronger acid than \(X\)

(d) Explain why \(Z\) is a stronger acid than \(Y\)

Equation Transcription:

Text Transcription:

CH_2

NH

OH

W,pKa=25

X,pKa=23

Y,pKa=8.8

Z,pKa=4.2

X

W

Y

X

Z

Y

ANSWER:

Solution 47SP

(a)

The structure of the conjugate base for compound W is follows:

Its resonance structures are as follows:

The structure of the conjugate base for compound X is follows:

Its resonance structures are as follows:

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