Question 1: (5 marks - 3 for 1H NMR and 2 for 13C NMR)) Please draw the 1H-NMR and 13C-NMR spectra for the molecule shown. Be sure to indicate the approximate chemical shifts for the expected signals. In the 1H-NMR please also be sure to indicate the correct coupling patterns and integrations. Please use the symbols 1H, 2H 3H, 4H above each signal to indicate the number of hydrogen atoms responsible for each signal. HO 8 7 6 5 4 3 2 Chemical Shift (ppm) 200 180 160 140 120 100 80 60 40 10 Chemical Shift (ppm) 20 OH

6) a)Assign the peaks in the 'H NMR shown below to the correct protons in molecule shown below. The portion of the NMR between 8-6.5 ppm has been magnified for easier viewing. (Hint: Draw resonance structures to distinguish the benzene and alkene Hs. 1H 2H 1H الس 2H CHH BH. CH3 A CH3 D H3C N H CH3 H 6H 6H PPM b) Draw a resonance that shows how you can differentiate the alkene hydrogens in the NMR. It is ok to have more than one positive and negative charge for the resonance structures with a NO2 group.) H H3C-N CH3 CH3 CH3

Below are the ¹H NMR spectrum of triphenylmethanol, benzophenone, and bromobenzene. Identify the compound corresponding to each ¹H NMR spectrum and draw the structure next to the ¹H NMR spectrum. Assign ALL peaks in each of the three ¹H NMR spectra. Hint: Conjugated systems (benzophenone) including an electronegative atom will cause a more downfield shift of ring protons in ¹H NMR compared with non-conjugated systems (bromobenzene). 8 8 8 7 7 7 6 6 6 5 5 5 4 PPM 4 PPM 4 PPM 3 3 3 2 2 2 1 1 1 0 0 0

In the attached H1-NMR, draw and identify each set of equivalent hydrogens in the structure and list peak they belong to in the NMR spectrum.

1. How many different sets of equivalent aromatic (benzene ring) carbons can be seen in the 13C NMR spectrum of your unknown monosubstituted benzene starting material? A. Are there any peaks for non-aromatic carbons in the 13C NMR spectrum of your unknown monosubstituted benzene starting material (yes or no)? B. If yes for part A, please list the corresponding ppm value(s) for any non-aromatic carbon(s)?

The product molecule of the experiment would produce 12 signals had we obtained an H¹-NMR spectrum. Label each proton group clearly on the molecule structure and list them with the correct multiplicity and the appropriate chemical shift range from the chemical shift chart. H3C

5. Dibromomethane contains 2 equivalent protons, so just one signal on the H NMR spectrum for dibramomethane is expected to be seen. determine the expected chemical shift for the dibromomethane signal.

Please help

Please help me with 1 and 2 thank you

For the molecules below how many signals for an 1H and 13C NMR will show?