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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

When an optically active carboxylic acid such as (R)-2-phenylpropanoic acid is brominated under Hell鈥揤olhard鈥揨elinskii conditions, is the product optically active or racemic? Explain.

Draw structures for the enol tautomers of the following compounds:

(a) Cyclopentanone

(b) Methyl thioacetate

(c) Ethyl acetate

(d) Propanal

(e) Acetic acid

(f) Phenylacetone

How might you convert geraniol into either ethyl geranylacetate or geranylacetone?

Predict the product(s) and provide the mechanism for each reaction below.

Show how you might prepare 1-penten-3-one from 3-pentanone.
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