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Chapter 13: Q 44. (page 523)

Question: Morphine, heroin, and oxycodone are three addicting analgesic narcotics. How could IR spectroscopy be used to distinguish these three compounds from each other?

Short Answer

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Answer

The structures of morphine, heroin, and oxycodone are distinguished via infrared spectroscopic techniques based on the particular compound's frequency and wavelength.

Step by step solution

01

IR spectroscopy

The IR spectroscopy gives information about the structure elucidation and functional group.IR spectroscopies differentiate functional groups in a given structure.

02

Structure determination

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Most popular questions from this chapter

Question: The mass spectrum of the following compound shows fragments at m/z = 127, 113, and 85. Propose structures for the ions that give rise to these peaks.

Question: What are the major IR absorptions in the functional group region for each compound?

Question: Which of the following has higher energy:

(a) IR light of 3000 cm−1or 1500 cm−1in wavenumber;

(b) IR light having a wavelength of 10 µm or 20 µm?

Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH3 forms compound A. A has a molecular ion in its mass spectrum at 154 and a strong peak in its IR spectrum at 1730 cm-1. Without added NaOCOCH3, oxidation of citronellol with PCC yields isopulegone, which is then converted to B with aqueous base. B has a molecular ion at 152, and a peak in its IR spectrum at 1680 cm-1.

a. Identify the structures of A and B.

b. Draw a mechanism for the conversion of citronellol to isopulegone.

c. Draw a mechanism for the conversion of isopulegone to B.

Question:Propose a structure consistent with each set of data.

a. a compound that contains a benzene ring and has a molecular ion at m/z= 107

b. a hydrocarbon that contains only sp3 hybridized carbons and a molecular ion at m/z= 84

c. a compound that contains a carbonyl group and gives a molecular ion at m/z= 114

d. a compound that contains C, H, N, and O and has an exact mass for the molecular ion at

101.0841
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