100- [3] 50 - 10 20 30 40 50 60 70 80 90 100 m/z Relative abunda nce

#8) Using the following spectra and other information provided, identify the compound. Assign pertinent peaks in the spectra. Label the peaks on the spectrum and place the structure of the compound in the box on the right side of the spectrum - Identify correct compound - label proton spectrum - label carbon spectrum

2. READ THE DIRECTIONS TO EACH QUESTION CAREFULLY - not following the directions means you get the question wrong! 3. FORMAT YOUR ANSWERS AS DIRECTED - formatting your answers incorrect means you get the question wrong! 4. Below are the IR regions and NMR chemical shifts table for use with the spectroscopy problems: 'H NMR 12 11 R 20 ΟΞΟ 10 OH R 0=C H 9 8 7 ppm 6 OH H C=C-H 5 NH H-C-X H-C-O -OH X = F, Cl, Br (i.e. electronegative atom) 3 -NH 2 H-C-N H-C-S HC- 1 -CH3 -CH₂- CEC-H H-C-C=O -CH H-C-C=C 0 4000 DID small range range of values broad peak =C-H ⇓ 3250- 3300 N-H broad with spikes -3300 -O-H broad-3300 -3400 3500 -O-H -CEN N-H CO I, I =C H 2730- 2820 道 H 3000- 2 peaks 3100 -C-H 2850- 2960 0 -C-O-H broad-3000 3000 usually strong -CEN B 2200 -CICH 3 2200 2500 wavenumber, cm-¹ 2000 C C HC N 1680 OR 1730 200 C. H 1600- 1660 0.585 1710 C. NA₂ 1650 3 1600 O 1500 *** 1000

The base peak in the mass spectrum of benzyl bromide (PhCH2Br) has a m/z of 91. Draw the structure of this fragment ion.