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Problem

This document provides 12 problems involving the analysis of infrared spectroscopy (IR) and nuclear magnetic resonance (NMR) data to determine molecular structures. Each problem provides the molecular formula and both the IR and NMR spectra. The problems are meant to help understanding of interpreting spectroscopic data and determining correlations between peaks and molecular structures.

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dsyda
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180 views

Problem

This document provides 12 problems involving the analysis of infrared spectroscopy (IR) and nuclear magnetic resonance (NMR) data to determine molecular structures. Each problem provides the molecular formula and both the IR and NMR spectra. The problems are meant to help understanding of interpreting spectroscopic data and determining correlations between peaks and molecular structures.

Uploaded by

dsyda
Copyright
© Attribution Non-Commercial (BY-NC)
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
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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

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