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The following compound can become protonated on any of the

Chapter 1, Problem 39SP

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QUESTION:

The following compound can become protonated on any of the three nitrogen atoms. One of these nitrogens is much more basic than the others, however.

(a) Draw the important resonance forms of the products of protonation on each of the three nitrogen atoms.

(b) Determine which nitrogen atom is the most basic.

Equation Transcription:

Text Transcription:

CH_3

NH

C

NH

NH_2

Questions & Answers

QUESTION:

The following compound can become protonated on any of the three nitrogen atoms. One of these nitrogens is much more basic than the others, however.

(a) Draw the important resonance forms of the products of protonation on each of the three nitrogen atoms.

(b) Determine which nitrogen atom is the most basic.

Equation Transcription:

Text Transcription:

CH_3

NH

C

NH

NH_2

ANSWER:

Solution:

The following compound can become protonated on any of the three nitrogen atoms , it can be represented as,

ac.png

(resonance structure)

Step 1

Protonation of NH #1

Protonation of NH #2

Protonation of NH#3

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