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Chapter 13: Q25P (page 594)

Question:Rank the following compounds from highest wavenumber to lowest wavenumber for their C=O absorption bands:

a.

b.

Short Answer

Expert verified

Answer

The decreasing order of wavenumber is as shown below.

a.

b.

Step by step solution

01

Inductive electron-withdrawing group

The group that attracts the ring鈥檚 electron toward itself is the electron-withdrawing group.The oxygen of the ester group has electron-withdrawing nature; that鈥檚 why the double bond character of the carbonyl group increases, and its wavenumber is the highest.

02

Electron donating group

The group that releases its electrons to the ring is the electron-donating group. If the concentration of hydrogen molecules is higher, its O-H stretch absorption wavenumber is high. While a diluted solution with less hydrogen bonding or no hydrogen bonding has less O-H stretching absorption wavenumber.

03

Ring size

The size of the ring increases the stretching wavenumber decreases.

So, the order is as follows.

a.

b.

Order of decreasing wavenumber

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Most popular questions from this chapter

Which shows an absorption band at a larger wavenumber: a carbonyl group bonded to a sp3 carbon or a carbonyl group bonded to an sp2 carbon of an alkene?

Draw structures for a saturated hydrocarbon that has a molecular ion with an m/zvalue of 128.

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Rank the following compounds from highest wavenumber to lowest wavenumber for their C卢O absorption band:

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