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Chapter 21: Q9. (page 824)

Question: Which carbonyl group in each pair absorbs at a higher frequency?

a.

b.

Short Answer

Expert verified

Answer

a. (E)-but-2-enal absorbs at a higher frequency.

b. Cyclopropanone absorbs at a higher frequency

Step by step solution

01

Step-by-Step Solution Step 1: Effect of conjugation on wavenumber

If conjugation is present in a compound, it possesses a lower wavenumber. This is because the carbonyl group loses its double-bond character and shifts frequency closer to C-O.

02

Explanation for higher wavenumber

a.

The given compounds are shown below:

Given structures

In the first compound, the double bond is in conjugation with the carbonyl group. Due to this, it has a lower wavenumber as compared to the second compound.

b.

The given compounds are shown below:

Given structures

As the ring size increases, the strain of the ring decreases. Thus, the smaller the ring, the higher will be the wavenumber.

Cyclopropanone has more strain, due to which it possesses a higher wavenumber.

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Most popular questions from this chapter

Question: Draw the structure of all constitutional isomers that contain a ketone and have molecular formula C5H10O. Give the IUPAC name for each isomer and state how C13NMR spectroscopy could be used to distinguish these isomers.

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Devise a synthesis of each compound from ethanol as the only source of carbon atoms. You may use any other organic or inorganic reagents you choose.

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