15.19 Draw the expected H NMR spectrum for each of the following compounds: 15.2

Question

15.19 Draw the expected H NMR spectrum for each of the following compounds: 15.20 Gamma-hydroxybutyric acid (GHB) is used in the treatment of excessive daytime sleepiness (narcolepsy), but when mixed with alcohol, it can cause loss of consciousness, which explains why it is sometimes referred to as a "date rape drug." As a result, college students should always keep an eye on their drinks, and emergency room doctors should always keep up-to-date on the latest treat- ment protocols for GHB intoxication. Draw the expected 'H NMR spectrum of GHB. ?? ?? y-Hydroxybutyric acid (GHB)

Explanation / Answer

15.19 Exprected NMR

(a) would show peaks at,

1.2 ppm (quintet, 2H) for CH2 between two CH2's

1.4 ppm (quintet, 2H) for CH2 between two CH2's

2.1 ppm (triplet, 2H) for CH2 between CH2 and C=O group

3.6 ppm (triplet, 2H) for CH2 between CH2 and Oxygen

(b) would show peaks at,

1.2 ppm (singlet, 6H) for 2 CH3

1.4 ppm (triplet, 2H) for CH2 next to CH2

3.5 ppm (triplet, 2H) for CH2 between CH2 and Oxygen

4.3 ppm (singlet, 2H) for CH2 between oxygen and C=O group

9.9 ppm (singlet, 1H) for aldehydic proton

15.20.GHB mixed with alcohol are given to victims before sexual assault. The sedative effects of GHB causes the victims to be easily sexually exploited and thus, is called a day rape drug.

The typicall NMR of GHB would shown peaks at,

1.6 ppm (quintet, 2H) for CH2 between to CH2's

2.2 ppm (triplet, 2H) for CH2 between CH2 and C=O group

3.5 ppm (triplet, 2H) for CH2 between CH2 and oxygen

4.7 ppm (singlet, 1H) for -OH proton

11.0 ppm (singlet, 1H) for -COOH proton

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