IR Spectrum Analysis: Identifying the Major Functional Group

C=O Stretching Peak? s, 1750 1650 cm-1 YES O-H Stretching Peak? m, br. 3400-2400 cm-1 YES Carboxylic Acid1 NO NO N-H Stretching Peak? s, br. 1 2 @ 3500-3300, cm-1 2 1 @ 3500-3300, cm-1 YES NO Amide
2

NO Amine6
O-H Stretching Peak? m, br. 3400-3200 cm-1 N-H Stretching Peak? m, br.1 or 2 @ ca. 3500 3300 cm-1

YES N-H YES O-H Alcohol7

CC Stretching Peak? w-m, 2250-2100 cm-1 YES NO Is the alcohol a phenol? Alkyne8

C-O Stretching Peak? s, 1300-1000 cm-1 YES Ester3 NO

C-O Stretching Peak? s, 1300-1000 cm-1 YES NO Ether9

C-H Stretching Peak? 2 w, 2900-2700 cm-1 YES Aldehyde

4

C=C Stretching Peak? m-w, 1680-1600 YES

Aromatic10 YES

NO Ketone5

NO Alkane
12

C=C Ring Stretching? m-w, ca. 1600 & 1475 NO

Practice using this decision tree and notes on the next page with the provided sample spectra to make sure you see how the different parts "fit" Don't forget to confirm your initial assignment with other characteristic peaks for the identified functional group Don't forget to check for other functional groups that may be present

Alkene11

D.S. Frohnapfel, 2007

Additional Notes on IR Spectrum Interpretation IMPORTANT! Don't forget that more than one type of functional group may be present in the molecule. Always check for characteristic bands of other classes once you have identified the class of compound. This is especially important to check for aromatic rings. Phenyl rings often appear as substituent groups in other classes of compounds. 1. Carboxylic Acids: Typical C=O stretch for acids is around 1710 cm-1 A C-O stretch at 1300-1000 cm-1 should also be present 2. Amides: Typical C=O stretch for amides is generally <1700 cm-1 N-H deformation bands may be visible around 1650-1500 cm-1. these are often obscured by the C=O stretch 3. Esters: Typical C=O stretch for esters is around 1735 cm-1 A C-O stretch around 1300-1000 cm-1 should also be present. The C-O stretch of esters is often as strong or stronger than the C=O stretch 4. Aldehydes: Typical C=O stretch for aldehydes is around 1725 cm-1 2 weak C-H stretching bands should be present around 2900-2700 cm-1 5. Ketones: Typical C=O stretch for ketones is around 1715 cm-1 6. Amines: N-H deformation bands should be present 1 amine 2 bands around 1640 1560 2 amine 1 band around 1500 7. Alcohols: C-O stretch around 1150-1100 should be present Check for C=C ring stretches to see if a phenol compound is present. 8. Alkynes: Terminal alkynes will have a C-H stretch around 3300 cm-1 NOTE: Symmetric alkynes do not have an active CC stretching band. These are easily misidentified as alkanes spectra. There are other tests that can distinguish the two. 9. Ethers: IR Spectra similar to alkanes. The primary difference is the C=O (1750-1730 cm-1) and C-O (13001000 cm-1) stretching peaks 10. Aromatic Ring: C-H stretching above 3000 cm-1should be present Strong C-H out-of-plane bending bands should be present 1000-700 cm-1 Also look for overtone bands in the baseline in the carbonyl region (2000-1667 cm-1) 11. Alkenes: A C-H stretching band should be present around 3100-3000 cm-1 C-H- out-of-plane bending bands should be present 1700-1000 cm-1 (higher E than aromatic) 12. Alkanes: Most spectra will have the characteristic C-H stretches around 3000 2850cm-1 and the C-H bending bands around 1450 & 1375. It is the absence of other characteristic bands that allows you to classify the compound as an alkane. The spectra of alkyl halides are highly similar to alkanes usually can't be distinguished by IR The spectra for cycloalkanes will lack the CH3 umbrella deformation at 1380-1370 cm-1 The CH3 umbrella deformation splits into two bands (ca. 1380 & 1360 cm-1) for alkanes havine a gemdimethyl terminus (iso-alkyl substituents, iso-alkanes)