
Concept explainers
Interpretation:
Two compounds are to be identified on the basis of their chemical formulas, and IR and
Concept introduction:
Peaks in an IR spectrum help in determining
In 13C NMR spectroscopy, we get information about the different types of carbon present in the given molecular formula.
13C NMR spectroscopy can even differentiate between primary, secondary, tertiary, and quaternary carbons.
If the compound only contains C, H, and O, the index of hydrogen deficiency is calculated as
If a compound contains C, H, O, and a halogen, the halogen can be treated as if it were a hydrogen for the purpose of calculating index of hydrogen deficiency.

Answer to Problem 35P
Solution:
a) The structure of the compound
b) The structure of the compound
Explanation of Solution
The chemical formula of the compound is
The count of four indicates the possibility of a benzene ring. If a benzene ring is present, the oxygen atom would be singly bonded, either as a hydroxyl group or as an ether functional group.
The IR and 13C NMR spectra of the compound are as follows:
The presence of a broad peak around 3200
Chemical formula of the compound is
Therefore this compound also is likely to have a benzene ring.
The IR and 13C NMR spectra of the compound are as follows:
Two peaks in the IR spectrum, at about 700 and 750
Therefore, the structure of the compound is
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Chapter 23 Solutions
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

