(e) Sketch the 1H NMR spectrum of benzoyl ferrocene I. Indicate the chemical shift range of the 1H NMR signals and their relatively intensity (integration) and assign the signals. O=C -0. Fe -0 |

What effect does increasing the operating frequency of a 1H NMRspectrum have on each value: (a) the chemical shift in 5; (b) thefrequency of an absorption in Hz; (c) the magnitude of a couplingconstant J in Hz?

Describe the 1H-NMR spectrum of 4-bromoaniline (chemical shift, integration, multiple). Make a table and describe the results.

For the following 9 compounds (most of which were the ones used in this lab), tell me what peaks you would expect to see in the 'H-NMR spectrum of those compounds. I have provided table for you to fill out with approximate chemical shift (ppm units), peak multiplicity_(singlet, doublet, etc.) and integration of the signal (how many protons would give that signal). No IR data is required. In addition, tell me the number of 13C-NMR signals you would expect to see [specific 13C shifts are not required] Predict

7) The correct structure that corresponds to the spectroscopic data given below is [IR 2720, 1710 1 point cm*1. 1H NMR 9.80(s, 1H), 7.50(dd, J = 8,0Hz, 2Hz, 1H), 7.40(d, J = 2.0Hz, 1H), 6.90(d, J = 8.0Hz, 1H), 3.90(s, 3H), 3.80(s, 3H)] COOH OMe Me CHO OMe OMe CHO OMe OMe COOH OMe Me

3c A doublet signal appeared in the 1H NMR spectrum that was analysed on 400 MHz NMR given below. Calculate the coupling constant (J) of this signal.

The IR spectrum of 2-methyl-1-butanol (H;CCH,CH(CH;) CH,OH) and tert-butyl methyl ether [(CH;);COCH3] are shown below. Assign cach spectrum to the correct com- pound and identify the frequencies and the functional groups used to support your assignment. λ (μm) 6 7 8 9 10 11 12 1314 15 2.5 100 3 5 90 80 70 60 50 40 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Frequency (cm-1) A (µm) 7 8 9 10 11 12 13 14 15 2.5 100 3 5 20 4 6 90 80 70 60 50 40 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Frequency (cm¬!) (%) Transmission (%) Transmission 20

Interpret 1HNMR peaks of ethyl acetate include structure

The 'H NMR of allyl bromide is given. Assign the signals to different protons. In spin decoupling experiments, what effect will be observed on irradiation at 8 (i) 6.0 and (ii) 3.9. Clearly indicate multiplicity and coupling constant values in decoupling experiments. (c) 3.9 (d, J = 6.0 Hz, 2H) На. Hc 5.0 (dd, J = 8.0 and 2.0 Hz, 1H) 5.3 (dd, J = 12.0 and 2.0 Hz, 1H) Hb -Br Hd Hd 6.0 (ddt, J = 12.0, 8.0 Hz and 6.0 Hz, 1H) Long range coupling not given

Absorption bands in the region of 1600-1700 cm-1 are often used for quantification of caffeine. What does the bands in this region refer to?