a. How many types of hydrogen are present, assuming no serious overlap between different types? _____
b. What is the chemical shift of the hydrogen type that is most shielded? ______
c. Consider the multiplicity, which derives from spin-spin coupling. What best describes the most shielded hydrogen type? ____Singlet ____Doublet ____Triplet ____Quartet ____Doublet of doublets
d. What does this multiplicity indicate about the most shielded hydrogens? _____There is one hydrogen present at this position _____There are two hydrogens present at this position _____There are three hydrogens present at this position _____There are two hydrogens on the neighboring carbon _____There are three hydrogens on the neighboring carbon
e. If the molecular formula of the compound is C 3 H 7 Br, what does the integration show about the most shielded hydrogens? _____There is one hydrogen present at this position _____There are two hydrogens present at this position 2 _____There are three hydrogens present at this position _____There are two hydrogens on the neighboring carbon _____There are three hydrogens on the neighboring carbon
f. What can you conclude about the most shielded hydrogens, using the above evidence? _____They represent a CH2 group, attached to another CH2. _____They represent a CH2 group, attached to a CH3. _____They represent a CH3 group, attached to a CH2. _____They represent a CH3 group, attached to another CH3. _____They represent a CH2 group, attached to CH.
g. What is the chemical shift of the hydrogen type that is most deshielded? _____
h. Knowing that the formula for this compound is C 3 H 7 Br, what does the chemical shift of these deshielded hydrogens suggest? _____There is an aromatic ring attached at this position _____There is a bromine attached at this position _____The aromatic ring is at the other end of the molecule _____The bromine is at the other end of the molecule
i. How many hydrogens are present at this deshielded position? _____1 _____2 _____3 _____4 _____5
j. How many hydrogens are present on the carbon adjacent to the deshielded position? _____1 _____2 _____3 _____4 _____5
2. When an external magnetic field is applied, what happens to the protons in a sample? _____All protons align with the field. _____All protons align opposite to the field. _____Some protons align with the field and some align opposite to it. _____All protons assume a random orientation.
3 3. Which of the following compounds gives a 1 H NMR spectrum consisting of only a singlet, triplet and quintet? _____CH 3 OCH 2 CH 2 CH 2 CH 2 OH _____CH 3 OCH 2 CH 2 OCH 2 CH 3
_____CH 3 OCH 2 CH 2 CH 2 OCH 3
_____CH 3 OCH 2 CH(CH 3 )OCH 3
4. What is the splitting pattern of the methylene protons in propane? _____triplet _____quartet _____doublet _____septet
5. A compound of formula C5H12 gives 1 signal in the 1H NMR and 2 signals in the 13C NMR. The compound is _____pentane. _____2-methylbutane. _____2,2-dimethylpropane. _____Cannot tell without more information.
6. There are several compounds with the molecular formula C5H10Br2. Which isomer ad with this formula has the following 1H NMR spectrum? ! (ppm) 1.0 (9H, singlet), 5.3 (1H, singlet)
_____a _____b _____c _____d
7. Which of the following combinations of peaks appears in the 1H NMR spectrum of 1,4- dimethyoxyethane, CH3OCH2CH2CH2CH2OCH3? _____three singlets _____a singlet, a triplet, and a quintet _____a singlet and two triplets _____a doublet and a triplet
4 8. Propose a structure for the compound C 7 H 9 N with the spectra below
3. (25 points total) Answer the questions below about the structure that has MW = 107 and the following NMR spectra: 5 0 1 2 3 4 5 6 7 8 9 10 2 H, J=7.9 HZ 1 H, J=7.9 HZ PPM 6 H,s 200 180 160 140 120 100 80 60 40 20 0 PPM Figure by MIT OCW. 5 9. Propose a structure for the compound C 8 H 8 O 2 with the spectra below 1H NMR 3.75 ppm (s, 6H), 6.83 ppm (s, 4H) 13C NMR 153, 114, and 56 ppm
6 10. Which C 9 H 10 O compound gives the following 1 H NMR spectrum?
11. Identify the compound (C 4 H 8 O) that gives the following 1 H NMR spectrum.
7 12. Predict the features expected in the 1 H NMR for the compound shown by completing the table below. (Label equivalent sets of protons H a , H b , etc. for clarity.)
protons type approximate ppm multiplicity J nm (Hz) reason for J integral H a
H b
H c
H d
H e
Assign each 13 C signal seen in the NMRs of the compounds below to the carbon giving rise to the signal.
13.
1. 165 ppm 2. 147 ppm 3. 87 ppm 4. 42 ppm
14.
1. 81 ppm 2. 30 ppm
O O H 2 C O Cl Cl 8
15.
1. 176 ppm 2. 170 ppm 3. 134 ppm 4. 131 ppm 5. 38 ppm HO O CH 2 OH O