2. (Chapter 13 - Q58b) The compound whose H NMR spectrum is shown has the molecular formula C7H7B1. Follow the following questions to predict the unknown structure. Chem. shift Rel. area 2.31 1.50 701 1.00 7.35 1.00 TMS 10 7 6 O ppm 4 3 2 Chemical shift (8) e20s Cenge leaming 2(a) Degree of the unsaturation of this compound is= 2(b) The two distinct peaks in the aromatic region of the H NMR indicate that compound is .disubstituted = 2(c) The splitting pattern of the peak at 2.31 ő is = 2(d) The group that corresponds to the splitting pattern in 1(c) is = 2(e) This compound has the plane of symmetry Yes or No = 2(f) The name of the unknown compound = Intensity

7. The following compounds are isomeric esters derived from acetic acid, each with formula C5H10O2. Draw the structures of the two esters?

Calculate the degree of unsaturation. Assign the relevant peaks in the IR spectrum. Assign the peaks in the 13C NMR spectrum. Assign the peaks in the 1H NMR spectrum.

Identify the compound from the compound bank based on the NMR data.

8. Using the provided chart, predict the proton 'H NMR spectrum of acetaminophen Assignment a b C d e H3C Expected ppm H H "Ha Expected integration Expected multiplicity

Which C gH 100 compound gives the following 'H NMR spectrum? 3H 3H 2H 2H PPM 1 2 3 O a. 1 O b.2 Oc.3 O d.4 P Type here to search

Draw the product structure and label each unique hydrogen atom with a letter. Label the NMR spectral peaks with letters corresponding to each hydrogen atom.

3. (Chapter 13 - Q58c) The compound whose H NMR spectrum is shown has the molecular formula C3H9B1. Follow the following questions to predict the unknown structure. Chem. Rel. shift area 3.16 1.00 3.56 1.00 1.00 1.50 Z18 729 TMS 10 O ppm Chemical shift (8) ng 3(a) Degree of the unsaturation of this compound = 3(b) The two peaks at 3.16 8 and 3.56 ő indicate two triplets Yes or NO = 3(c) The compound has 2 CH2 groups Yes or No = 3(d) Depending on the two triplets' chemical shifts one of the CH2 may have attached to the Br, Yes or No = 3(e) The multiplet at 7.18 õ to 7.29 õ indicate that compound is. disubstituted benzene - 3(f) The name of the unknown compound is = Intensity