Chapter 21: Q78E (page 726)
Assign structures to compounds with the following 1H NMR spectra:
(a)C5H9ClO2
IR:1735 cm-1
Short Answer
Thestructure of the compound using 1H NMR spectra can be drawn.
Chapter 21: Q78E (page 726)
Assign structures to compounds with the following 1H NMR spectra:
(a)C5H9ClO2
IR:1735 cm-1
Thestructure of the compound using 1H NMR spectra can be drawn.
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Get started for free21-73 N,N-Diethyl-m-toluamide (DEET) is the active ingredient in manyinsect repellent preparations. How might you synthesize this substancefrom m-bromotoluene?
21-46 Draw structures corresponding to the following names
Bacteria typically develop a resistance to penicillins and other β-lactam antibiotics (see Something Extra in this chapter) due to bacterial synthesis of β -lactamase enzymes. Tazobactam, however, is able to inhibit the activity of the β -lactamase by trapping it, thereby preventing a resistance from developing.
(a) The first step in trapping is the reaction of a hydroxyl group on the β -lactamase to open the β -lactam ring of tazobactam. Show the mechanism.
(b) The second step is opening the sulfur-containing ring in tazobactam to give an acyclic imine intermediate. Show the mechanism.
(c) Cyclization of the imine intermediate gives the trapped β-lactamase product. Show the mechanism.
21-36 When 4-dimethylaminopyridine (DMAP) is added in catalytic amountsto acetic anhydride and an alcohol, it significantly increases the rate of ester formation. The process begins with a reaction between acetic anhydride and DMAP to form a highly reactive acetylpyridinium intermediate that is more reactive than acetic anhydride itself. Propose a mechanism for this process that includes the formation and reaction of the acetylpyridinium intermediate.
Propose structures for compounds that have the following formulas and IR absorptions:
(a) C6H12O2, 1735 cm-1
(b) C4H9NO, 1650 cm-1
(c) C4H5ClO, 1780 cm-1
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