nmr problem set - chemistry.bd.psu.educhemistry.bd.psu.edu/justik/chem 212/chem 212 nmr problem...
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CHEM%212% NMR%Problem%Set!!
X% Spring!2014!!
1. Formulas!for!each!NMR!are!given!below.!!Use!the!HDI!calculation!to!tell!you!how!many!rings/double!bonds/triple!bonds!are!possible! in! your!molecule.! !Remember! that!an!HDI!≥�4!usually! suggest!an!aromatic!ring.!!
2. For!each!NMR!follow!the!steps!in!order!to!start!elucidating!the!structure.!• Determine!number!of!proton!families!• Classify!resonances!by!chemical!shift!• Determine!fragments!by!integration!(CH,!CH2,!CH3…etc.)!
!3. When!finished,!look!at!your!answer!and!ask!yourself!if!given!this!compound,!would!you!observe!the!
NMR!you!were!given?!!
Page! Formula! ! Page!! Formula!
1!! C6H3Cl3! ! 11! C9H10O2!
2!! C3H7I! ! 12! C4H8O!
3!! C10H12O! ! 13! C7H8O!
4!! C4H9Br!! ! 14! C5H12O!
5!! C6H12O!! ! 15! C8H6!
6!! C7H5IO2! ! 16!!! C9H12!!
7!! C5H10O2! ! 17! C9H10O!
8!! C6H4ClNO2! ! 18! C5H10O2!
9!! C7H6O! ! 19! C8H8O2!
10!! C7H7Br! ! 20! C6H15N!
!
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
1 1
1 1
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
2 2
2 2
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
3 3
3 3
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
4 4
4 4
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
5 5
5 5
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0
Offset: 1.6 ppm.
DMSO-d6 QE-300
6 6
6 6
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0
Offset: 0.3 ppm.
CDCl3 QE-300
7 7
7 7
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
8 8
8 8
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
9 9
9 9
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
10 10
10 10
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
11 11
11 11
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
12 12
12 12
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
13 13
13 13
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
14 14
14 14
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
15 15
15 15
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
16 16
16 16
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
17 17
17 17
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
18 18
18 18
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
19 19
19 19
12 11 10 9 8 7 6 5 4 3 2 1 0
240 220 200 180 160 140 120 100 80 60 40 20 0CDCl3 QE-300
20 20
20 20
Answer Key for the 1H NMR spectra:
Page Answer Page Answer 1 Cl
Cl
Cl
11
O
O
2 I 12CO
H
3 O 13 OH
4 Br 14 O
5 O 15C CH
6
I
OH
O 16
7
HO
O 17 O
8 N
Cl
OO 18
O
O
9 C
H
O 19
OH
O
10 Br 20 N