Question

1. In the H NMR, draw the structure of the molecule directly on the spectrum and identify each unique proton. Indicate which proton is responsible for each peak.

2. In the IR spectrum, indicate which functional group is responsible for each important peak. Attempt to identify at least five important peaks. In you discussion, indicate which peaks are most helpful in determining whether or not you converted the starting material to the desired product.

3. Compare the IR spectrum of your pure product to the other IR spectrum, especially in the fingerprint region in both spectra. Using the fingerprint absorption table, you will be able to determine the substitution pattern for your pure compound.

4. What product did you isolate and what evidence do you have to support this claim?

In your analysis of the NMR and IR data, please be sure to address the specific pieces of information available from each spectrum that allow you to identify the product molecule as 1) a specific isomer and/or 2) different than the starting material. Chemical shift values (NMR) and wavenumber (IR) values are important to discuss here.

Calculate the percent yield for the iodination product Calculate the percent recovery for the iodination product 으.att!용(preproduct). 0-4639(crude pa-oo = 10.1% o 463 8 Crude pos) In the space below, draw a curved-arrow mechanism for the iodination reaction. Show all important reso- nance structures for any carbocation intermediates 心:Base 9 OH Appearance of isolated iodination product hhitel clear crystals Literature appearance: Observed mp range: 2o-alo ca Observed mo range. 2or Alo c ondly,Lterature mp range cuda Literature mp range:

Answer 1

1)

H NMR
13.10 ppm	Chemical shift of hyroxyl proton
8.50 ppm	Chemical shift of aromatic proton
8.09 ppm	Chemical shift of aromatic proton
7.99 ppm	Chemical shift of aromatic proton
7.46 ppm	Chemical shift of aromatic proton
6.95 ppm	Chemical shift of aromatic proton

2) peak at 751 cm-1 for 1,2-substitution of salicylamide.

wavelength	group
3397 cm-1	– NH stretch
3191 cm-1	– OH stretch
1671 cm-1	– C=O stretch
1630cm-1	– NH bend
1591 and 1493 cm-1	– aromatic ring stretch.

answer 3)

700 - 900 cm-1	Finger print region
729.14 cm-1	1,2 - disubstituted pattern of aromatic ring
779.46cm-1	1, 2, 3 - trisubstituted pattern of aromatic ring
Salicylamide
751 cm-1	indicative of 1,2-Disubstituted		strong peak, so major product

4) Para-substituted product should be isolated. but looking at the IR spectra it seems that 1,2, 3 - trisubstituted pattern ring was isolated