Step 1: Brief Description The given compound is 4-aminobenzoic acid. The IR and NMR spectrum of this compound also given. Determine the spectrum. Step 2: Determination of IR data The peaks are identified as following: Two bands at 3300 & 3230 cm. This is due to asymmetrical and symmetrical N-H stretching of NH₂ group. A broad stretching between $200-2500 cm** - This broad stretching is due to O-H in carboxylic acid group. Band at 1680-1700 cm¹. C=O Stretching 1600 cm C-C-C (aromatic carbon) Step 3: Determination of PMR spectrum Splitting patterns: It should be noted that spin-spin splitting is observed only between nonequivalent neighboring protons. Equivalent protons do spin-spin couple with one another but splitting is not observed. Chemical shift: A highly shielded proton has a low chemical shift and a highly deshielded proton has a high value of chemical shift. The given peaks are of following: Proton Level Chemical shift (ppm) Relative integration Multiplicity ABC -11.9 7.8 8.3 broad singlet (N-H D -5.9 2H proton) 2H %%%% 1H broad singlet (OH proton) 2H doublet doublet C. The amine group is considered to be electron donating toward the ring by resonance, thus it will place a partial negative charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. H H d. The carboxylic acid is considered to be electron withdrawing by resonance, thus it will place a partial positive charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. e. Based on the resonance structures, which of the aromatic protons is more shielded and which is less shielded? Which of these protons will appear at the larger chemical shift and which will appear at the lower chemical shift? Decide which of the protons should be labelled as HB and Hc. Explain briefly.

THIS CAN NOT BE HAND DRAWN! MUST USE A COMPUTER or DIGITALLY ILLUSTRATE

A student performed a series of reactions and obtained the spectral data provided. The reaction sequence is shown below.. What are the structures for A, B, C, and D? Compound B NMR (relative integrated areas below peaks) CH;CH,O°N 1. BHTHF N-bromosuccnimide A CH;CH,OH B 2. H,O,/OH- D hv reflux Compound A NMR (relative integrated areas below peaks) PPM 5 Compound B IR INFRARED SPECTRUM PPM 5 1 6 0.8 Compound A IR INFRARED SPECTRUM 0.6 0.8 0.4 0.4 0.2- 3000 2000 Wavenumber (cm-1) 1000 The MS of compound B shows an M+ peak at 198 and an M+2 peak at 200 with a relative abundance of 1:0.97 2000 Wavenumber (cm-1) 3000 1000 Transmitance Relative Transmittance

label the IR peaks draw the structure of the compound and give reasoning

Please don't provide handwritten solution ....

Match the four structures with the four IR spectra (by putting a proper letter in the box to the right of each spectrum). Use specific IR absorptions for various functional groups to identify the structures.

Given the information about the unknown: Unknown: MP: 101-106 oC White solid   IR: 2837, 1701, 1602, 1391, 1139 cm-1 ** Using the Reference sheet, The IR and the given  H-NMR, and C-NMR. Deduce, what  the unknown is. Please give the name of uknown

label IR peaks and draw the structure of the compound and explain reasoning for the structure