COMBINED PROBLEM #1COMBINED PROBLEM #1

C4H10O

PROBLEM 1 INFRARED SPECTRUMPROBLEM 1 INFRARED SPECTRUM

PROBLEM 1 NMR SPECTRUMPROBLEM 1 NMR SPECTRUM

C4H10O

6

1

1

2

doublet multiplet doublet

COMBINED PROBLEM #2COMBINED PROBLEM #2

C9H10O2

PROBLEM 2 INFRARED SPECTRUMPROBLEM 2 INFRARED SPECTRUM

1719

PROBLEM 2 NMR SPECTRUMPROBLEM 2 NMR SPECTRUM

C9H10O2

5

23

quartet triplettwo multiplets

acid

BASIC INFRARED KNOWLEDGEBASIC INFRARED KNOWLEDGE

OH 3600NH 3400

CH 3000

C N 2250C C 2150

C=O 1715

C=C 1650

C-O 1100

3300 3100 2900 2850 2750

3000

1800 1735 1725 1715 1710 1690

=C-H -C-H-CHO

C-H

ketoneesteracidchloride

aldehydeamide

anhydride : 1810 and 1760

CH2 and CH3 bend : 1465 and 1365

BASE VALUES

Also remember the effects of H-bonding, conjugation and ring size.

benzene C=C : between 1400 and 1600

EXPANDED CH

EXPANDED C=O

NMR Correlation ChartNMR Correlation Chart

12 11 10 9 8 7 6 5 4 3 2 1 0

-OH -NH

CH2FCH2ClCH2BrCH2ICH2OCH2NO2

CH2ArCH2NR2

CH2SC C-HC=C-CH2

CH2-C-O

C-CH-C

C

C-CH2-CC-CH3

RCOOH RCHO C=C

H

TMS

HCHCl3 ,

(ppm)

DOWNFIELD UPFIELD

DESHIELDED SHIELDED

Ranges can be defined for different general types of protons.This chart is general, the next slide is more definite.

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

R-CH3 0.7 - 1.3

R-C=C-C-H 1.6 - 2.6

R-C-C-H 2.1 - 2.4

O

O

RO-C-C-H 2.1 - 2.5O

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-N-C-H 2.2 - 2.9

R-S-C-H 2.0 - 3.0

I-C-H 2.0 - 4.0

Br-C-H 2.7 - 4.1

Cl-C-H 3.1 - 4.1

RO-C-H 3.2 - 3.8

HO-C-H 3.2 - 3.8

R-C-O-C-H 3.5 - 4.8

O

R-C=C-H

H

6.5 - 8.0

R-C-H

O

9.0 - 10.0

R-C-O-H

O

11.0 - 12.0

O2N-C-H 4.1 - 4.3

F-C-H 4.2 - 4.8

R3CH 1.4 - 1.7R-CH2-R 1.2 - 1.4 4.5 - 6.5

R-N-H 0.5 - 4.0 Ar-N-H 3.0 - 5.0 R-S-H

R-O-H 0.5 - 5.0 Ar-O-H 4.0 - 7.0

R-C-N-H

O

5.0 - 9.0

1.0 - 4.0R-C C-H 1.7 - 2.7

Monosubstituted

cis-1,2-

trans-1,2-

1,1-

Trisubstituted

Tetrasubstituted

C CH

R H

H

C CH

R R

H

C CR

H R

H

C CR

R R

R

C CR

R R

H

C CR

R H

H

Disubstituted

10 11 12 13 14 15

1000 900 800 700 cm-1

s s

m

s

s

s

=C-H OUT OF PLANE BENDING

ALKENES

10 11 12 13 14 15

1000 900 800 700 cm-1

Monosubstituted

Disubstituted

ortho

meta

para

Trisubstituted

1,2,4

1,2,3

1,3,5

BENZENES

s s

s

s s

s

s

s

s

m

m

m

mOOPS

RING H’s

combination bands