Using Table 10-2 of your textbook, assign chemical shift values to the proton or protons indicated in the following NMR spectra. In case of a multiplet, give the d value at the middle of the range. a) b) H(a) -H (b) (c) CH3 (a) 50. `H (b) CH3–C–CH,CH2–C−O−CH2CH3 (a) (b) (c) ő (d) (e) 10 10 8.0 9 9 8 7.0 6.0 6 5.0 5 4 4.0 PPM (6) 3 3.0 22 3 2.0 1 1 3 0 (ppm) 0 (ppm) 1.0 0

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Chapter1: Chemical Foundations
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Table 10.2 is also attached. Please help!

Table 10.2 Typical Hydrogen Chemical Shifts in Organic Molecules
Type of hydrogenª
Primary alkyl, RCH3
Secondary alkyl, RCH₂R'
Tertiary alkyl, R,CH
Allylic (next to a double bond), R₂C=C
`'R'
Benzylic (next to a benzene ring), ArCH₂R
Ketone, RCCH3
Alkyne, RC=CH
Chloroalkane, RCH₂Cl
Bromoalkane, RCH₂Br
Iodoalkane, RCH₂I
Ether, RCH₂OR'
Alcohol, RCH₂OH
Terminal alkene, R₂C=CH₂
Internal alkene, R₂C=CH
Aromatic, ArH
Aldehyde, RCH
Alcoholic hydroxy, ROH
Thiol, RSH
Amine, RNH₂
"R, R', alkyl groups; Ar, aromatic group (not argon).
pall of barba
11
3000 Hz
H
Carboxylic
acid
H
Aldehyde
10
CH3
9
Downfield
H
Aromatic
8
7
0.8-1.0
1.2-1.4
1.4-1.7
1.6-1.9
2.2-2.5
2.1-2.6
1.7-3.1
3.6-3.8
3.4-3.6
3.1-3.3
3.3-3.9
3.3-4.0
4.6-5.0
5.2-5.7
6.0-9.5
9.5-9.9
0.5-5.0
0.5-5.0
0.5-5.0
6
}
}
1500
ppm (8)
5
Alkane and alkane-like hydrogens
Chemical shift 8 in ppm
Hydrogens adjacent to unsaturated functional groups
Hydrogens adjacent to electronegative atoms
Alkenyl
Alkene hydrogens
(variable)
(variable)
(variable)
900
Upfield
-C=C-H
Alkynyl
-C-H
T
X
X = electron
withdrawing
600
3
C-C-
Allylic
2
300
C-H
Saturated
0
0
Transcribed Image Text:Table 10.2 Typical Hydrogen Chemical Shifts in Organic Molecules Type of hydrogenª Primary alkyl, RCH3 Secondary alkyl, RCH₂R' Tertiary alkyl, R,CH Allylic (next to a double bond), R₂C=C `'R' Benzylic (next to a benzene ring), ArCH₂R Ketone, RCCH3 Alkyne, RC=CH Chloroalkane, RCH₂Cl Bromoalkane, RCH₂Br Iodoalkane, RCH₂I Ether, RCH₂OR' Alcohol, RCH₂OH Terminal alkene, R₂C=CH₂ Internal alkene, R₂C=CH Aromatic, ArH Aldehyde, RCH Alcoholic hydroxy, ROH Thiol, RSH Amine, RNH₂ "R, R', alkyl groups; Ar, aromatic group (not argon). pall of barba 11 3000 Hz H Carboxylic acid H Aldehyde 10 CH3 9 Downfield H Aromatic 8 7 0.8-1.0 1.2-1.4 1.4-1.7 1.6-1.9 2.2-2.5 2.1-2.6 1.7-3.1 3.6-3.8 3.4-3.6 3.1-3.3 3.3-3.9 3.3-4.0 4.6-5.0 5.2-5.7 6.0-9.5 9.5-9.9 0.5-5.0 0.5-5.0 0.5-5.0 6 } } 1500 ppm (8) 5 Alkane and alkane-like hydrogens Chemical shift 8 in ppm Hydrogens adjacent to unsaturated functional groups Hydrogens adjacent to electronegative atoms Alkenyl Alkene hydrogens (variable) (variable) (variable) 900 Upfield -C=C-H Alkynyl -C-H T X X = electron withdrawing 600 3 C-C- Allylic 2 300 C-H Saturated 0 0
Using Table 10-2 of your textbook, assign chemical shift values to the proton or
protons indicated in the following NMR spectra. In case of a multiplet, give the d
value at the middle of the range.
a)
b)
O
H
(a)
-H (b)
H
¹(c)
CH3 (a)
5.
`H (b)
CH3–C–CH,CH2–C-O–CH2–CH3
(a) (b) (c)
(d) (e)
10
10
8.0
9
9
7.0
8
8
7
7
6.0
6
5.0
5
5
4
4
4.0
PPM (6)
3
3
3.0
2
3
2.0
1
0 (ppm)
0 (ppm)
1.0
0
Transcribed Image Text:Using Table 10-2 of your textbook, assign chemical shift values to the proton or protons indicated in the following NMR spectra. In case of a multiplet, give the d value at the middle of the range. a) b) O H (a) -H (b) H ¹(c) CH3 (a) 5. `H (b) CH3–C–CH,CH2–C-O–CH2–CH3 (a) (b) (c) (d) (e) 10 10 8.0 9 9 7.0 8 8 7 7 6.0 6 5.0 5 5 4 4 4.0 PPM (6) 3 3 3.0 2 3 2.0 1 0 (ppm) 0 (ppm) 1.0 0
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