TWELVE EASY PROBLEMS

COMBINED PROBLEMS FORMULA + INFRARED + NMR

Spectra in these problems were obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ 2002)

(Mar

NOTE ON INTEGRALS: Integrals (relative number of hydrogens) are given as: 2 The integrals are the simplest ratio. Expansions are blue and printed above the baseline.

PROBLEM 1 INFRARED SPECTRUM

C4H10 O

COMBINED PROBLEM #1

PROBLEM 1 NMR SPECTRUM 6

C4H10 O

doublet

multiplet

doublet

COMBINED PROBLEM #2

PROBLEM 2 INFRARED SPECTRUM

C9H10 O2

1719

PROBLEM 2 NMR SPECTRUM

C9H10 O2
5

3 2

two multiplets

quartet

triplet

COMBINED PROBLEM #3

PROBLEM 3 INFRARED SPECTRUM

C10H12 O

1688

PROBLEM 3 NMR SPECTRUM

C10H1 2O

septet

doublet

COMBINED PROBLEM #4

PROBLEM 4 INFRARED SPECTRUM

C5H10 O2

1712

PROBLEM 4 NMR SPECTRUM

C5H10 O2
two overlapping multiplets (2 + 2)

triplet

triplet

COMBINED PROBLEM #5

PROBLEM 5 INFRARED SPECTRUM

C9H 12

PROBLEM 5 NMR SPECTRUM

C9H 12
5

septet

doublet

COMBINED PROBLEM #6

PROBLEM 6 INFRARED SPECTRUM

C9H 12

1610

PROBLEM 6 NMR SPECTRUM

C9H 12
1

COMBINED PROBLEM #7

PROBLEM 7 INFRARED SPECTRUM

C6H10 O3

1731

1719

PROBLEM 7 NMR SPECTRUM

C6H10 O3
2 2

3 3

quartet

triplet

COMBINED PROBLEM #8

PROBLEM 8 INFRARED SPECTRUM

C5H7N O2

2266

1749

PROBLEM 8 NMR SPECTRUM

C5H7N O2

2 3

quarte t

triplet

COMBINED PROBLEM #9

PROBLEM 9 INFRARED SPECTRUM

C9H12 O

PROBLEM 9 NMR SPECTRUM

C9H12 O
5

3 1 1 2

triplet

quinte t

triplet

COMBINED PROBLEM #10

PROBLEM 10 INFRARED SPECTRUM

C8H12 O4

1730

PROBLEM 10 NMR SPECTRUM 400 MHz 3

C8H12 O4
1 2

quartet

triplet

COMBINED PROBLEM #11

PROBLEM 11 INFRARED SPECTRUM

C7H12 O4

1735

PROBLEM 11 NMR SPECTRUM 400 MHz 3

C7H12 O4

1 2

quartet

triplet

COMBINED PROBLEM #12

PROBLEM 12 INFRARED SPECTRUM

C8H7 N

2229

PROBLEM 12 NMR SPECTRUM 400 MHz 3

C8H7 N

CORRELATION CHARTS

BASIC INFRARED KNOWLEDGE

BASE VALUES
OH 3600 NH 3400 CH 3000 C N C C C=O C=C 2250 2150 1715 1650 3300 3000 3100
EXPANDED CH

2900

C-H =CH

-C-H

2850 2750

-CHO

CH2 and CH3 bend : 1465 and 1365

1800 1735 1725 1715 1710 1690

C-O 1100

aldehyd acid acid ester e keton chloride e anhydride : 1810 and 1760

amid e

EXPANDED C=O

benzene C=C : between 1400 and 1600 Also remember the effects of H-bonding, conjugation and ring

NMR Correlation Chart

DOWNFIELD DESHIELDED -OH -NH CHCl3 H , UPFIELD SHIELDED TMS

1 2

1 1

1 0

H RCOOH RCHO C= C

(ppm) CH2F CH2Cl CH2Br CH2I CH2O CH2NO 2 CH2Ar CH2NR2 CH2S C C-H C=CCH2 CH2-CO C-CH-C C C-CH2C C-CH3

Ranges can be defined for different general types of protons.

APPROXIMATE CHEMICAL SHIFT RANGES (ppm) FOR SELECTED TYPES OF PROTONS

R-CH3 R-CH2-R R3CH

0.7 - 1.3 1.2 - 1.4 1.4 - 1.7 1.6 - 2.6

R-N-C-H R-S-C-H I-C-H Br-C-H

2.2 - 2.9 2.0 - 3.0 2.0 - 4.0 2.7 - 4.1

R-C=C-H 4.5 6.5 H 6.5 O8.0 R-C-N-H 5.0 9.0 O R-C-H 9.0 10.0 O R-C-O-H 11.0 12.0

R-C=C-C-H O R-C-C-H O

2.1 - 2.4

Cl-C-H 3.1 - 4.1 RO-C-H HO-C-H O R-C-O-C-H O2N-C-H F-C-H 3.2 - 3.8 3.2 - 3.8 3.5 - 4.8 4.1 - 4.3 4.2 - 4.8

RO-C-C-H 2.1 - 2.5 O HO-C-C-H 2.1 - 2.5 N C-C-H 2.1 - 3.0 R-C C-C-H 2.1 - 3.0

C-H 2.3 2.7 R-C C-H 1.7 - 2.7

R-N-H 0.5 - 4.0 Ar-N-H 3.0 - 5.0 RR-O-H 0.5 - 5.0 Ar-O-H 4.0 - 1.0 S-H

ALKENES

10
R H C C H R C C H H R C C R R C C R R C C R R C C R R H R H R H H H H R

11 15 s s

12

13

14

Monosubstitute d Disubstitute d cis-1,2-

trans1,21,1-

Trisubstitute d Tetrasubstitute d

=C-H OUT OF PLANE BENDING

100

90

80

70 cm-

BENZENES

10 15

11

12

13 s s

14 s

Monosubstitute d Disubstitute d orth o met a par a Trisubstitute d 1,2, 4 1,2, 3 1,3, 5 s 100 90 80 m s s

RING Hs OOPS m s s m m 70 cm-

combination