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CHEM%212% NMR%Problem%Set%2!!
X% Spring!2014!
!
1. In!this!set!formulas!are!not!provided.!!Functional!group!information!is!given!in!a!general!form.!!C=O!
may!indicate!an!aldehyde!or!ketone,!for!example.!!An!amine!can!indicate!1o,!2o!or!3o!amine.!!Carbon!
based!functional!groups!(alkane,!alkene,!alkyne!and!aromatic)!are!not!provided.!
!
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!or!IR!Data! ! Page!! Formula!or!IR!Data!
1!! Br! ! 17! ester!
2!! COOH!&!Br! ! 18! C=O!
3!! Cl! ! 19! ether!
4!! OH!&!Cl! ! 20! ester!&!Br!
5!! C=O! ! 21! ester!
6!! COOH!&!I! ! 22! ether!!
7!! C=O! ! 23! ester!
8!! C=O! ! 24! C=O!
9!! Br!&!C=O! ! 25! ester!&!Cl!
10!! COOH!&!Br! ! 26! amine!
11! Cl!&!OH! ! 27! amine!
12! Cl!&!OH! ! 28! ester!
13! amine! ! 29! ester!
14! Br!&!amine! ! 30! amine!
15! Cl!&!OH! ! 31! ester!
16! C=O! ! 32! C=O!
! ! ! 33! Br!
!
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
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: 0.4 ppm.
CDCl3 QE-300 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
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 0QE-300
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
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
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
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
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
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
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
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 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
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
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
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
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
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
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
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
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
21 21
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
22 22
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
23 23
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
24 24
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
25 25
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
26 26
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
27 27
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
28 28
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
29 29
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
30 30
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
31 31
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
32 32
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
33 33
CHEM%212% NMR%Problem%Set%2!!
X% Spring!2014!!
1!!
!
8!!
!
15!
!
22!
!
29!
!2!!
!
9!!
!
16!
!
23!
!
30!
!
3!!
!
10!!
!
17!
!
24!
!
31!
!
4!!
!
11!
!
18!
!
25!
!
32!
!
5!!
!
12!
!
19!!
26!
!
33!!
6!!
!
13!
!
20!
!
27!
!
!!
7!!
!
14!
!
21!
!
28!
!
!!
!
Br O
HO
ClO
O
O
OHBrO O
BrO
O
OH2N
Cl
HO
O
Br O
OO
O
O
Cl
OHHO Cl
O
H
Cl
O
OH
O
O
OHClO N Br
I
O
OHH2N
O
O
BrNH2
O
H2N
Br
O
O O
O
34 34
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