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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

A mass spectrum shows significant peaks at m/z = 87, 115, 140, and 143. Which of the following compounds is responsible for that mass spectrum?

Question:How do you know that the absorption band at -1700cm-1in figure 13.23 is due to a C-O bond and not a C-N bond.

a. How could you use IR spectroscopy to determine whether the following reaction had occurred?

b. After purifying the product, how could you determine whether all the NH2NH2had been removed?

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

A 4.0脳10-5solution of a compound in hexane shows an absorbance of 0.40 at 252 nm in a cell with a 1 cm light path. What is the molar absorptivity of the compound in hexane at 252 nm?
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