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IR Absorption Bands of Functional Groups in Organic Compounds Functional Group Wavenumber (cm-1) 2850-3000 1450-1470 1370-1380 800-1200 720-725

3060-3140 1620-1680 900-1000 3300-3320 2100-2140 600-700 3200-3600 Alcohol 3600-3700 1000-1200 Ether Primary amine Secondary amine Nitrile Aldehyde Ketone Carboxylic acid Ester Amide 1050-1150 3200-3400 3200-3400 2220-2280 1700-1720 2700-2850 1680-1720 1700-1720 3000 1730-1750 1000-1300 1650-1690 3200-3400 3000-3150 1750-1950 600-900 1550 and 1400 2350 Comments CH stretch for sp3 carbon (Strong) CH bend (Strong) CH methyl umbrella bend (Medium) CC stretch (many medium bands) CH bend (Medium) CH stretch for sp2 carbon (Medium) C=C stretch (Medium) CH bend (Strong) CH stretch for sp carbon (Medium) CC stretch (medium) CH bend (Strong) Hbonded OH stretch (Broad strong band) Free OH stretch (sharp medium band, present only in dilute samples) CO stretch (strong, higher for more substituents on carbon) CO stretch NH stretch (two medium bands) NH stretch (single medium band) NC stretch (medium) C=O stretch (Strong) Aldehyde CH stretch, two medium bands C=O stretch (Strong) C=O stretch (Strong) OH stretch (very broad band, usually with a spike of sp3 CH stretch in the middle) C=O stretch (Strong) CO stretch C=O stretch (Strong) NH stretch (two bands for primary, one for secondary, none for tertiary amide) CH stretch (variable) CH bending overtone region (usually several weak bands of similar strength) CH bend (strong) Walrus teeth NO stretch bands Doublet (positive or negative, depending on variation in local concentration between baseline and sample measurement)

Alkane

Alkene Terminal alkyne (internal alkynes lack unique bands)

Aromatic Nitro Carbon dioxide

Predicting Chemical Shifts for 1H-NMR Spectra (adapted from Table 12.4, J.M. Hornback Organic Chemistry, 1998) Type of Hydrogen
C CH3 C C CH3

Chemical Shift () 0.9 1.6 1.8 Variable (1-4) Variable (2-5) 2.0 2.2 2.2 2.2 2.2 2.3

Type of Hydrogen
Br Cl CH3 CH3

Chemical Shift () 2.7 3.0 3.3 3.7 4.1 4.2 5.5-6.5 7-8 Variable (6-8) 10 12

C CH
N H

O CH3

O C O CH3
O2N CH3 F CH3

O H
O C O C CH3

O C CH3

C C H

N CH3
I CH3

O C N H O C H
O C O H

N C CH3

CH3

Procedure: Find the functional group near the proton of interest. Take the chemical shift listed and: Add 0.3 if CH2 instead of CH3, or add 0.7 if CH instead of CH3. Add 0.3 for electronegative group or atom attached to the adjacent carbon. When two electronegative groups are attached to the same carbon, both groups affect the hydrogens: add the indicated values from the table together, add the correction for the methylenyl or methinyl hydrogen, and subtract 0.9 from the total. The value obtained by these calculations is a prediction, and may deviate from observed values by 1 ppm or more.

Group Methyl Methylene Methine Alkyl chloride Alkyl bromide Alkyl iodide Carbonyl (amide, carboxylic acid, ester)

NMR Chemical Shifts Chemical Shift Group 5-40 Ether 15-55 Alkyne 25-60 Alkene 40-50 Aromatic 30-40 Alcohol 5-15 Amine 150-185 Carbonyl (aldehyde, ketone)

13C

Chemical Shift 55-90 60-90 100-170 90-160 45-90 10-70 175-220

Substituent Effects on Electrophilic Aromatic Substitution Group Effect Regiochemistry


R

NH2
O R H N C R
R

N R

OH
S R O O C R
Ar

Strongly activating

Ortho/para

Moderately activating Weakly activating Weakly deactivating

Ortho/para

Ortho/para Ortho/para

O C H O C NH2
C N R NH3

O C R O C O R
SO3H

O C OH

Moderately deactivating

Meta

CX3

N R R

NO2

Strongly deactivating

Meta