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Chapter 22: Q8P (page 738)

Draw a resonance structure of the acetonitrileanion,

andaccount for the acidity of nitriles.

Short Answer

Expert verified

The acidity of nitriles occurs due to the removal of a proton and its stable conjugate base stabilised by resonance.

Step by step solution

01

Resonance structure of acetonitrile anion

The resonance structure of acetonitrile anion as

02

Explanation of the resonance structure of acetonitrile anion

Acetonitrile has the formula

The Hydrogens in the methyl groups are acidic in nature as they are attached to the electron withdrawing nitrile group. Now, removal of a proton forms an anion

This anion is stabilized by resonance.

03

Acidity of nitriles

The acidity of nitriles occurs due to the removal of a proton which is also stabilized by resonance.

04

Conclusion

Hence, you can draw the resonance structure of acetonitrile anion as

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Most popular questions from this chapter

How would you synthesize the following compounds from cyclohexanone?

More than one step may be required.

Although 2-substituted 2-cyclopentenones are in a base-catalyzed equilibrium with their 5-substituted 2-cyclopentenone isomers (Problem 22-55), the analogous isomerization is not observed for 2-substituted 2-cyclohexenones. Explain.

Which, if any, of the following compounds can be prepared by an acetoacetic ester synthesis? Explain.

The final step in attempting to synthesize Laurene, a hydrocarbon isolated from the marine alga Laurencia glandulifera,involved the Wittig reaction shown. The product obtained, however, was not Laurene but an isomer. Propose a mechanism to account for these unexpected results.

Question: Identify the most acidic Hydrogens in each of the following molecules:

(a)CH3CH2CHO

(b)(CH3)3CCOCH3

(c)CH3CO2H

(d)Benzamide

(e)CH3CH2CH2CN

(f)CH3CON(CH3)2
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