10. C4H,Br 100 80- 68- 42 20- 2922 8L82 1379 602T 1151

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.SE: Something Extra
Problem 40MP
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SPECTROSCOPY DRY LAB
General Formula to calculate the degree of unsaturation:
#C atoms - (#H atoms/2) + 1
Example: Benzene (C6H6) 6 - (6/2) + 1 = 4
Rules for calculating unsaturation with organic compounds that contain heteroatoms
(halogen, O, S, N)
Rule 1) Replace any halogens with hydrogens
Example: CH3B change to CH4 and then calculate 1- (4/2) + 1 = 0
Rule 2) Ignore any O or S atoms in the compound
Example: Phenol (C6H5OH) calculate for C6H6 6- (6/2) + 1 = 4
Rule 3) Subtract a H for every Nitrogen present
Example: Aniline (C6H5NH2) calculate for C6H6 6- (6/2) + 1 = 4
For the following problems given spectral data and the chemical formula:
1) Determine the degree of unsatuaration using the unsaturation rules above and list it in the
appropriate box:
2) Label important absorption bands directly on the IR spectra
3) Identify and label all signals directly on the 1H NMR and or 13C NMR spectra (make sure to
use Ha, Hb, Ca, Cb, etc...
Remember TMS shows up as a singlet at 0 ppm for both the 1H and the 13C NMR
CDCI3 (solvent) sometimes shows up as a triplet around 77pm in a 1°C NMR
4) Propose a structure for the compound that matches 1-3 above (If your structure has more
than four degrees of unsaturation it's quite likely to have an aromatic ring). Draw the
SKELETAL structure in the proposed structure box.
Transcribed Image Text:SPECTROSCOPY DRY LAB General Formula to calculate the degree of unsaturation: #C atoms - (#H atoms/2) + 1 Example: Benzene (C6H6) 6 - (6/2) + 1 = 4 Rules for calculating unsaturation with organic compounds that contain heteroatoms (halogen, O, S, N) Rule 1) Replace any halogens with hydrogens Example: CH3B change to CH4 and then calculate 1- (4/2) + 1 = 0 Rule 2) Ignore any O or S atoms in the compound Example: Phenol (C6H5OH) calculate for C6H6 6- (6/2) + 1 = 4 Rule 3) Subtract a H for every Nitrogen present Example: Aniline (C6H5NH2) calculate for C6H6 6- (6/2) + 1 = 4 For the following problems given spectral data and the chemical formula: 1) Determine the degree of unsatuaration using the unsaturation rules above and list it in the appropriate box: 2) Label important absorption bands directly on the IR spectra 3) Identify and label all signals directly on the 1H NMR and or 13C NMR spectra (make sure to use Ha, Hb, Ca, Cb, etc... Remember TMS shows up as a singlet at 0 ppm for both the 1H and the 13C NMR CDCI3 (solvent) sometimes shows up as a triplet around 77pm in a 1°C NMR 4) Propose a structure for the compound that matches 1-3 above (If your structure has more than four degrees of unsaturation it's quite likely to have an aromatic ring). Draw the SKELETAL structure in the proposed structure box.
10. СН,Br
10-
80-
60-
40-
20-
4200
3508
302
2508
2002
1500
1000
3H
3H
2H
1H
elle
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0 PPM
0.5
Degree of Unsaturation:
Proposed Structure:
00
180
160
140
120
100
80
60
40
20
CDS-03-177
ppm
ISTT
GLET
- 95T
Transcribed Image Text:10. СН,Br 10- 80- 60- 40- 20- 4200 3508 302 2508 2002 1500 1000 3H 3H 2H 1H elle 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 PPM 0.5 Degree of Unsaturation: Proposed Structure: 00 180 160 140 120 100 80 60 40 20 CDS-03-177 ppm ISTT GLET - 95T
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