Infrared Spectroscopy

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1 Carbonyl Compounds Cl H H N cm -1 (band 1) 1800 cm cm -1 both present (band 2) 1735 cm cm cm cm cm -1 Inductive Effects esonance Effects stronger bond W W W stronger bond weaker bond weaker bond D D D

2 Carbonyl Compounds Cl H H N cm -1 (band 1) 1800 cm cm -1 both present (band 2) 1735 cm cm cm cm cm -1 Inductive Effects Hydrogen Bonding H H H H C weaker bond H H weaker bond

3 Carbonyl Compounds ther Factors that Influence Position of C= Absorbance 1. Conjugation conjugation shifts carbonyl absorbance right cm -1 ; additional unsaturation 15 cm -1 H H H H 1727 cm cm cm cm cm cm -1 may see two bands s-cis s-trans

4 Carbonyl Compounds 1-penten-2-one C=C C=

5 Carbonyl Compounds ther Factors that Influence Position of C= Absorbance 2. ing Size (Angle Strain) decreasing ring size shifts carbonyl absorbance to higher frequencies 1717 cm cm cm cm -1 NH NH 1666 cm cm -1

6 Carbonyl Compounds ther Factors that Influence Position of C= Absorbance 3. Alpha Substituion the presence of an electronegative group at the a position shifts the C= stretch to the right (10-45 cm -1 ) Cl 1715 cm cm -1 influence by both inductive and field effects δ - X δ + X δ - δ + X withdraws electron density from carbonyl (inductive effect) strengthens C= bond repulsion of nonbonding electrons on (field effect) strengthens C= bond

7 Carbonyl Compounds ther Factors that Influence Position of C= Absorbance 3. Alpha Substituion magnitude of shift is influenced by conformation Cl H ' H ' ' Cl Cl A B C syn-eclipsed (cis) anti-staggered (gauche) H H 1713 cm -1 H Cl H Cl 1750 cm cm -1 H may see multiple absorbances

8 Carbonyl Compounds methyl chloroacetate Cl CH 3 C=

9 Carbonyl Compounds ther Factors that Influence Position of C= Absorbance 4. Internal Hydrogen-Bonding effects can be additive Me Me 1729 cm -1 H 1680 cm -1 Me

10 Aldehydes C= stretch between cm -1 - typically about 1725 cm -1 for aliphatic aldehydes - absorbance is lowered by conjugation conjugated aldehydes: cm -1 C-H stretch of CH shows two weak bands ( and cm -1 ) - first band may be obscured by sp 3 C-H absorbances

11 Aldehydes octanal

12 Aldehydes crotonaldehyde

13 Ketones C= stretch between cm -1 - typically about 1715 cm -1 for aliphatic ketones - absorbance is lowered by conjugation conjugated ketones: cm -1 ; or lower if doubly conjugated - frequency increases with decreasing ring size bending vibration appears as medium intensity peak between cm -1 1,3-diketones give more complicated spectra

14 Ketones cyclohexanone overtone C=

15 Ketones mesityl oxide

16 Ketones 2,4-pentanedione H keto form enol form 1723 and 1706 cm and cm -1 -H H C= (ketone) C= (enol)

17 Carboxylic Acids -H stretch between cm -1 - typically very broad - absorbance often centered about sp 3 C-H region C= stretch appears between cm -1 - strong, usually more intense than than of aldehydes and ketones - conjugation moves absorption to lower frequency C- stretch between cm -1

18 Carboxylic Acids isobutyric acid

19 Carboxylic Acids benzoic acid (nujol)

20 Carboxylic Acids benzoic acid H 1-octanol H

21 Carboxylic Acids sodium benzoate - + Na symmetric stretch asymmetric stretch

22 Esters C= stretch appears between cm -1 - conjugation with C= moves absorption to lower frequencies (10-25 cm -1 ) (band moves to right) - conjugation with ester oxygen moves band to higher frequencies (15-25 cm -1 ) (band moves to left) - frequency increases with decreasing ring size C- stretch gives two bands between cm -1 - one often stronger than the other

23 Esters ethyl acetate CH 2 CH 3 C= C cm -1

24 Esters methyl benzoate 1724 cm -1

25 Esters phenylacetate C= C cm -1

26 Esters Effect of ing Size & Conjugation on C= Absorbance ring size effects effect of α,β-conjugation effect of conjugation with 1735 cm cm cm cm cm cm cm -1

27 Amides C= stretch between cm -1 N-H stretch occurs between cm -1 - signal varies with amide structure 1 amines show two bands (~3350 and 3180 cm -1 ) 2 amines have one band (~3300 cm -1 ) 3 amines have no absorbance in this region N-H bend vibrations between cm -1 N H N H N H 1 2 3

28 Amides isobutylamide NH 2 NH 2 C=

29 Amides N-methylacetamide

30 Amides N,N-dimethylacetamide N CH 3 CH 3

31 Amides Effect of ing Size on C= Absorbance NH NH NH 1660 cm cm cm -1

32 Acid Chlorides C= stretch occurs between cm -1 - conjugation shifts frequency to right ( cm -1 ) C-Cl stretch between cm -1

33 Acid Chlorides acetyl chloride benzoyl chloride

34 Acid Anhydrides C= stretch always has two bands - absorption at and cm -1 may vary in size - conjugation shifts frequency to right (lower frequency) - ring strain moves absorption to left (higher frequency) C- stretch - multiple bands between cm -1

35 Anhydrides propionic anhydride

36 Imines, ximes, and Hydrazones N ' N H N N' 2 imine oxime hydrazone C=N H cm cm cm -1

37 Imines, ximes, Hydrazones 2-butanone oxime N H N-H C=N (1665 cm -1 )

38 Imines, ximes, Hydrazones acetone dimethylhydrazone N NMe 2 C=N benzaldehyde phenylhydrazone H N N Ph N-H C=N (1602, 1593 cm -1 )

39 Nitriles, Isocyanates, and elated Compounds C N N C + - N N N N C N N C S nitrile isocyanate azide carbodiimide isothiocyanate 2250 cm cm -1 (broad) 2140 cm cm cm -1 ' C C C ' C allene carbon dioxide 1950 cm -1 (medium) 2349 cm -1

40 Nitriles cyclohexanecarbonitrile C N o-tolunitrile C N

41 Isocyanate and Isothiocyanate butyl isocyanate N=C= cyclohexane isothiocyanate N=C=S

42 Azides and Carbodiimides ethyl 2-azidoisovalerate N 3 N,N -dicyclohexylcarbodiimide N=C=N

43 Allenes 1,2-pentadiene sp 2 C-H H H C C C CH 3 CH 2 H N-H C=C=C C=N

44 ther Groups F Cl Br I fluorides chloride bromide iodide cm cm cm cm -1 N 2 nitro group cm cm -1 Ar N 2 nitro group cm cm -1 SH thiol 2550 cm -1

45 Halides carbontetrachloride iodoform I H C I I C-I stretch

46 Halides chloroform chloroform-d C-D Cl D C Cl Cl

47 Nitro Compounds 2-nitropropane N N 2

48 Thiols butanethiol S-H

49 What Can the I Tell You? Evaluation of Unknown Samples by I Preliminary Evaluation: Identification of Major Functional Groups - Determine what you might expect to see (peak position, # of peaks) for each of the possible major organic functional groups. - Determine which functional groups are potentially present. Is there a peak between cm -1? Consider and alcohol or amine how can you differentiate the two? - You may also be able to eliminate possibilities based on peaks that are not present (e.g. no C= stretch? esters, carboxylic acids, aldehydes and ketones are eliminated from consideration). - Consider also any special circumstances that could affect what you see (e.g. hydrogen bonding, amine substitution, etc.) Subsequent Evaluation: Indications of Minor Functional Groups - Consider the presence of minor functional groups including double and triple bonds, halides, nitro groups, ethers, etc. - Be very careful here. I spectra are usually very complex. Don't try to read more into the spectrum than is actually there.

50 Practice Problem 1 What does this I tell you about structure? C 8 H 12

51 Practice Problem 1 what does this I tell you about structure? C 8 H 12 (same compound, now I taken as solution in CCl 4 )

52 Practice Problem C 9 H 10 What does this I tell you about structure?

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