California State Polytechnic University, Pomona

Dr. Laurie S. Starkey, Organic Chemistry Lab CHM 318L

1H NMR Chemical Shifts
O
CH3
R CH3
H
O
H R2C CR CH3
ROCH3 RH
C H R H

O
NH2
RNH2
N H R NH2

O
OH
R OH ROH
O H

(ppm) 11 10 9 8 7 6 5 4 3 2 1 0

Protons on Carbon Protons on Oxygen/Nitrogen*

Type of C-H (ppm) Description of Proton Type of H (ppm) Description
R CH3 0.9 alkyl (methyl) ROH 0.5-5 alcohol

R CH2 R 1.3 alkyl (methylene) ArOH 4-7 phenol

O
R3C H 1.5-2 alkyl (methine) R C OH 10-13 carb. acid

CH3 1.8 allylic (C is next to a pi bond) RNH2 0.5-5 amine

O
R C CH3 2-2.3 to carbonyl (C is next to C=O) ArNH2 3-5 aniline
O
Ar CH3 2.3 benzylic (C is next to Ph)
R C NHR 5-9 amide

RC C H 2.5 alkynyl
*Protons on N or O typically have wide
ranges of expected chemical shifts; the
R2N CH3 2-3 to nitrogen (C is attached to N) actual value depends on the solvent used,
the concentration, temperature, etc.
R CH2 X 2-4 to halogen (C is attached to Cl, Br, I) Because these protons are acidic and,
therefore, exchangeable, they may be
RO CH3 3.8 to oxygen (C is attached to O) broad peaks and usually do not couple with
neighboring protons (typically they are
R CH2 F 4.5 to fluorine (C is attached to F) broad singlets). If a protic deuterated
solvent is used (e.g., D2O or CD3OD), then
H the NH and OH protons will exchange with
R2C CR 5-5.3 vinylic (H is attached to alkene C)
the deuterium and the peaks will shrink or
disappear entirely, since D (2H) does not
Ar H 7.3 aromatic (H is on phenyl ring) show up in the 1H NMR spectrum.
O R = alkyl group
R C H 9.7 aldehyde (H is on C=O) Ar = aromatic ring,
Note: aldehyde (-CHO) proton usually does not such as phenyl (Ph)
couple with neighboring H's so appears as a singlet