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Chapter 23: Q5. (page 924)

Question: Which C-Hbonds in the following molecules are acidic because the resulting conjugate base is resonance stabilized?

Short Answer

Expert verified

Answer

The most acidic C-H bonds are shown below.

Step by step solution

01

Definition of resonance

Resonance is defined as the way of representing the delocalization of pi electrons in a molecular system.It brings extra stability to the system.

02

Advantages of resonance

A structure that is capable of showing resonance has higher acidity as compared to those structures having no resonating structures. The hydrogen that has the highest acidity in the structure is shown below in the form of resonating structures.

Representation of the possible resonating structures

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Most popular questions from this chapter

Question: Acyclovir is an effective antiviral agent used to treat the herpes simplex virus. (a) Draw the enol form of acyclovir, and explain why it is aromatic. (b) Why is acyclovir typically drawn in its keto form, despite the fact that its enol is aromatic?

Question: Draw the enol or keto tautomer(s) of each compound.

Question: Both pentane-2,4-dione and ethyl acetoacetate have two carbonyl groups separated by a single carbon atom. Although an equilibrium mixture of pentane-2,4-dione tautomers contains 76% of the enol forms, an equilibrium mixture of ethyl acetoacetate tautomers contains only 8% of the enol forms. Suggest a reason for this difference.

Question: Which carbonyl compound in each pair exhibits the higher percentage of the enol tautomer?

Question: Synthesize each compound from ethyl acetoacetate. You may use any other organic or inorganic reagents.
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