Advanced Pharmaceutical Analysis H1 NMR Examples Lecture 5 50 Advanced Pharmaceutical Analysis H1 NMR Examples P 105 Dr. Baraa Ramzi

Example 1 The following compound, with the formula C4H8O, is an ester. Give its structure and assign the chemical shift values.

Example 1

Example 2 The following compound is a monosubstituted aromatic hydrocarbon with the formula C9H12 , Give its structure and assign the chemical shift values.

Example 2

Example 3 The following compound is a carboxylic acid that contains a bromine atom: C4H7O2Br. The peak at 10.97 ppm was moved onto the chart (which runs only from 0 to 8 ppm) for clarity. What is the structure of the compound?

Example 3

Example 4 The compound that gives the following NMR spectrum has the formula C3H6Br2. Draw the structure.

Example 4

Example 5 Draw the structure of an ether with formula C5H12O2 that fits the following NMR spectrum:

Example 5 THINKING ONLY

Example 6 Following are the NMR spectra of three isomeric esters with the formula C7H14O2, all derived from propanoic acid. Provide a structure for each.

Example 6 (A)

Example 6 (B)

Example 6 (C)

Example 7 The two isomeric compounds with the formula C3H5ClO2 have NMR spectra shown below , drow their structures.

Example 7 (A)

Example 7 (B)

Example 8 The two isomeric compounds with the formula C10H14 have NMR spectra shown below:

Example 8 (A)

Example 8 (B)

Example 9 The compound with the formula C8H11N has the NMR spectra shown below. The infrared spectrum shows a doublet at about 3350 cm-1.

Example 9 IHD=4

Example 10 The NMR spectra are shown for two isomeric compounds with formula C10H12O. Their IR shows strong band at 1715cm-1.

Example 10 (A)

Example 10 (B)

Example 11 The NMR spectra are shown in parts a, b, c, and d for four isomeric compounds with formula C10H12O2. Their infrared spectra show strong bands near 1735 cm-1

Example 11 (A)

Example 11 (B)

Example 11 (C)

Example 11 (D)

Example 12 Along with the following NMR spectrum, this compound, with formula C5H10O2, shows bands at 3450 cm-1 (broad) and 1713 cm-1 (strong) in the infrared spectrum. Draw its structure.

Example 12

Example 13 The NMR spectrum for an ester with formula C5H6O2 is shown below. The infrared spectrum shows medium-intensity bands at 3270 and 2118 cm-1 . Draw the structure of the compound.

Example 13

Example 14 The NMR spectrum is shown for a compound with formula C7H12O4. The infrared spectrum has strong absorption at 1740 cm-1 and has several strong bands in the range 1333 to 1035 cm -1. Draw the structure of this compound.

Example 14