Contoh IR

Table of characteristic proton NMR chemical shifts.
type of proton type of compound chemical shift range, ppm

RCH3 1˚ aliphatic 0.9
R2CH2 2˚ aliphatic 1.3
R3CH 3˚ aliphatic 1.5
C=C–H vinylic 4.6–5.9
C=C–H vinylic, conjugated 5.5–7.5
C!C–H acetylenic 2–3
Ar–H aromatic 6–8.5
Ar–C–H benzylic 2.2–3
C=C–CH3 allylic 1.7
HC–F fluorides 4–4.5
HC–Cl chlorides 3–4
HC–Br bromides 2.5–4
HC–I iodides 2–4
HC–OH alcohols 3.4–4
HC–OR ethers 3.3–4
RCOO–CH esters 3.7–4.1
HC–COOR esters 2–2.2
HC–COOH acids 2–2.6
HC–C=O carbonyl compounds 2–2.7
RCHO aldehydic 9–10
ROH hydroxylic 2–4
ArOH phenolic 4-12
C=C–OH enolic 15–17
RCOOH carboxylic 10–13.2
HC–NHR amine 1.5–2.0
RNH2 amino 1–5
RNHC(=O)R’ amides 5-8.5
Table of characteristic IR absorptions.*
frequency, cm–1 bond functional group

3640–3610 (s, sh) O–H stretch, free hydroxyl alcohols, phenols
3500–3200 (s,b) O–H stretch, H–bonded alcohols, phenols
3400–3250 (m) N–H stretch 1˚, 2˚ amines, amides
3300–2500 (m) O–H stretch carboxylic acids
3330–3270 (n, s) –C!C–H: C–H stretch alkynes (terminal)
3100–3000 (s) C–H stretch aromatics
3100–3000 (m) =C–H stretch alkenes
3000–2850 (m) C–H stretch alkanes
2830–2695 (m) H–C=O: C–H stretch aldehydes
2260–2210 (v) C!N stretch nitriles
2260–2100 (w) –C!C– stretch alkynes
1760–1665 (s) C=O stretch carbonyls (general)
1760–1690 (s) C=O stretch carboxylic acids
1750–1735 (s) C=O stretch esters, saturated aliphatic
1740–1720 (s) C=O stretch aldehydes, saturated aliphatic
1730–1715 (s) C=O stretch ", #–unsaturated esters
1715 (s) C=O stretch ketones, saturated aliphatic
1710–1685 (s) C=O stretch ", #–unsaturated aldehydes
1685–1666 (s) C=O stretch ", #–unsaturated ketones
1680–1640 (m) –C=C– stretch alkenes
1650–1580 (m) N–H bend 1˚ amines
1600–1585 (m) C–C stretch (in–ring) aromatics
1550–1475 (s) N–O asymmetric stretch nitro compounds
1500–1400 (m) C–C stretch (in–ring) aromatics
1470–1450 (m) C–H bend alkanes
1370–1350 (m) C–H rock alkanes
1360–1290 (m) N–O symmetric stretch nitro compounds
1335–1250 (s) C–N stretch aromatic amines
1320–1000 (s) C–O stretch alcohols, carboxylic acids, esters, ethers
1300–1150 (m) C–H wag (–CH2X) alkyl halides
1250–1020 (m) C–N stretch aliphatic amines
1000–650 (s) =C–H bend alkenes
950–910 (m) O–H bend carboxylic acids
910–665 (s, b) N–H wag 1˚, 2˚ amines
900–675 (s) C–H “oop” aromatics
850–550 (m) C–Cl stretch alkyl halides
725–720 (m) C–H rock alkanes
700–610 (b, s) –C!C–H: C–H bend alkynes
690–515 (m) C–Br stretch alkyl halides
* m = medium, w = weak, s = strong, n = narrow, b = broad, s = sharp.
Problem 1 http://chemistry.colorado.edu/Spectroscopy/Problems/1.html
Organic Chemistry at CU Boulder

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Problem 1
Formula: C H O
5 10
Spectroscopy Reference
Show Unsaturation answer
C H O
5 10
Rule 2, omit O, gives C H
5 10
5 - 10/2 + 1 = 1 degree of unsaturation.
Look for 1 pi bond or aliphatic ring.
1 dari 2 5/22/2014 10:10 PM

Show IR answer
The band at 1716 indicates a carbonyl, probably a ketone. The bands at 3000-2850 indicate C-H
alkane stretches.
Show Structure answer
This is the structure. See if you can assign the peaks on your own.
Show NMR answer
Problems list Next Problem
Original content © 2013 University of Colorado at Boulder, Department of Chemistry and Biochemistry. The information on these
pages is available for academic use without restriction. This page was last updated on January 15, 2014.
2 dari 2 5/22/2014 10:10 PM


Problem 2
Formula: C H O
7 14
C H O
7 14
7 14
1 dari 2 5/22/2014 10:12 PM

Show IR answer
alkane stretches.
Show NMR answer
Note that D and E are chemically similar enough that their peaks overlap.
Previous Problem Problems list Next Problem
2 dari 2 5/22/2014 10:12 PM


Problem 3
Formula: C H O
4 10
C H O
4 10
4 10
4 - 10/2 + 1 = 0 degrees of unsaturation.
1 dari 2 5/22/2014 10:13 PM

No pi bonds or rings.
Show IR answer
The broad band at 3339 indicates an O-H stretch, probably an alcohol. The bands at 3000-2850
indicate C-H alkane stretches. The band at 1041 is C-O stretch, consistent with an alcohol.
Show NMR answer
A and B do not couple because of A's ability to H-bond.
2 dari 2 5/22/2014 10:13 PM


Problem 4
Formula: C H O
6 14
C H O
6 14
6 14
1 dari 2 5/22/2014 10:15 PM

Show IR answer
The broad band at 3350 indicates O-H stretch, probably an alcohol. The bands at 3000-2850 indicate
C-H alkane stretches. The bands from 1320-1000 indicate C-O stretch, consistent with an alcohol.
Show NMR answer
As noted, C and D are not equivalent even though they're on the same carbon.
2 dari 2 5/22/2014 10:15 PM


Problem 5
Formula: C H O
4 8 2
C H O
4 8 2
4 8
1 dari 2 5/22/2014 10:15 PM

Show IR answer
The band at 1743 indicates a carbonyl, probably a saturated aliphatic ester. The bands at 3000-2850
indicate C-H alkane stretches. The bands in the region 1320-1000 could be due to C-O stretch,
consistent with an ester.
Show NMR answer
2 dari 2 5/22/2014 10:15 PM


Problem 6
Formula: C H O
5 10 2
C H O
5 10 2
5 10
1 dari 2 5/22/2014 10:16 PM

Show IR answer
The band at 1740 indicates a carbonyl, probably a saturated aliphatic ester. The bands at 3000-2850
indicate C-H alkane stretches. The bands in the region 1320-1000 could be due to C-O stretch,
consistent with an ester.
Show NMR answer
C has a higher chemical shift than D because it's closer to a more electron-withdrawing functional
group.
2 dari 2 5/22/2014 10:16 PM


Problem 7
Formula: C H O
8 14 3
1 dari 2 5/22/2014 10:17 PM

C H O
8 14 3
8 14
Look for 2 pi bonds or aliphatic rings, or 1 of each.
Show IR answer
The bands at 1745 and 1716 indicate that there are two carbonyls, probably an aliphatic ester and an
aliphatic ketone. The bands at 3000-2850 indicate C-H alkane stretches.
Show NMR answer
Even though A, B, C and D are all 2H peaks, they can be distinguished by chemical shift and splitting.
B is outside the normal range for protons next to carbonyls, because it's adjacent to both carbonyls
and the combined deshielding is higher than normal.
2 dari 2 5/22/2014 10:17 PM


Problem 8
Formula: C H O
5 10
1 dari 2 5/22/2014 10:17 PM

C H O
5 10
5 10
Show IR answer
The band at 1727 indicates a carbonyl, probably an aldehyde; an aldehyde is also suggested by the
band at 2719 which is likely the C-H stretch of the H-C=O group. The bands at 3000-2850 indicate
C-H alkane stretches.
Show NMR answer
2 dari 2 5/22/2014 10:17 PM


Problem 9
Formula: C H O
11 14 2
C H O
11 14 2
1 dari 2 5/22/2014 10:39 PM


11 14
Look for an aromatic ring, plus 1 other pi bond or aliphatic ring.
Show IR answer
The band at 1603 or 1894 might indicate a carbonyl outside the normal range; the small peak around
1800 indicates it may be an aldehyde. The band at 1510 is an aromatic ring. The bands at 3000-2850
indicate C-H alkane stretches.
Show NMR answer
Based on what is covered, you shouldn't need to distinguish between B and C, but you should be able
to tell that the ring is para-substituted.
2 dari 2 5/22/2014 10:39 PM


Problem 10
Formula: C H O
3 6 2
C H O
3 6 2
6 6
1 dari 2 5/22/2014 10:20 PM

Show IR answer
The band at 1716 indicates a carbonyl. The wide band from 3300-2500 is characteristic of the O-H
stretch of carboxylic acids. The bands at 3000-2850 indicate C-H alkane stretches. The bands in the
region 1320-1000 indicate the C-O stretch of carboxylic acids.
Show NMR answer
2 dari 2 5/22/2014 10:20 PM


Problem 11
Formula: C H O
8 8 2
C H O
8 8 2
8 8
Look for an aromatic ring, plus another pi bond or aliphatic ring.
1 dari 2 5/22/2014 10:22 PM

Show IR answer
The band at 1689 indicates a carbonyl, probably an acid. The broad dip at 2924 indicates the OH
group of the acid. The band at 1589 indicates an aromatic ring.
Show NMR answer
You are not expected to tell the aromatic Hs apart from each other, but you should be able to tell that
the ring is not para-substituted.
2 dari 2 5/22/2014 10:22 PM


Problem 12
Formula: C H N
7 9
C H N
7 9
Rule 3, omit the N and one H, gives C H
7 8
1 dari 2 5/22/2014 10:22 PM

Show IR answer
The two bands at 3433 and 3354 indicate a primary amine (-NH ). The bands at 3000-2850 indicate
2
C-H alkane stretches. The band at 3034 indicates aromatic C-H stretch; aromatics also show bands in
the regions 1600-1585 and 1500-1400 (C-C in-ring stretch), and 900-675 (C-H out-of-plane). C-N
stretch of aromatic amines would show up at 1335-1250 (there is a band in that region).
Show NMR answer
You are not expected to tell the aromatic Hs apart from each other, but you are expected to know that
the ring is not para-substituted.
2 dari 2 5/22/2014 10:22 PM


Problem 13
Formula: C H N
5 13
C H N
5 13
5 12
1 dari 2 5/22/2014 10:38 PM


Show IR answer
The two bands at 3388 and 3292 indicate a primary amine (-NH ). The bands at 3000-2850 indicate
2
C-H alkane stretches.
Show NMR answer
Note that C is showing as 2 2H peaks, instead of a 4H peak. This may be caused by a similar effect as
in Problem 4 - on each carbon C, the H closer to the N will be in a slightly different environment. If
the rotation of this carbon is hindered, these Hs may have a different chemical shift.
2 dari 2 5/22/2014 10:38 PM


Problem 14
Formula: C H O
8 14
1 dari 2 5/22/2014 10:24 PM

C H O
8 14
8 14
Look for any 2 of pi bonds or aliphatic rings.
Show IR answer
alkane stretches. Since the compound is an alkene, one would expect to see C=C stretch at
1680-1640; these weak bands are not seen in this IR (according to Silverstein, "the C=C stretching
mode of unconjugated alkenes usually shows moderate to weka absorption at 1667-1640"). Since the
compound is an alkene, C-H stretch should appear above 3000 (not seen: the absorption for this
single hydrogen must be too weak).
Show NMR answer
Here, the two E methyl groups have different chemical shifts because they are permanently locked
into different positions with respect to the alkene.
2 dari 2 5/22/2014 10:24 PM


Problem 15
Formula: C H Br
4 9
C H Br
4 9
Rule 1, replace halogens with hydrogens, gives C H
4 10
No pi bonds and no rings.
1 dari 2 5/22/2014 10:26 PM

Show IR answer
The bands at 3000-2850 indicate C-H alkane stretches. The bands in the region 1300-1150 could
indicate C-H wag (-CH Br) of an alkyl halide.
2
Show NMR answer
2 dari 2 5/22/2014 10:26 PM


Problem 16
Formula: C H O
10 14
C H O
10 14
10 14
1 dari 2 5/22/2014 10:26 PM

Look for an aromatic ring.
Show IR answer
The broad dip at 3250 indicates an OH group. The peak at 2963 indicates an alipahtic group. The
peaks at 1599 and 1514 indicate an aromatic ring.
Show NMR answer
You are not expected to tell the aromatic Hs apart from each other, but you should be able to tell that
the ring is para-substituted.
2 dari 2 5/22/2014 10:26 PM


Problem 17
Formula: C H O
13 10 3
C H O
13 10 3
13 10
1 dari 2 5/22/2014 10:27 PM

Look for 2 aromatic rings plus another pi bond or aliphatic ring.
Show IR answer
The band at 1682 indicates a carbonyl, probably an ester. The band at 3192 indicates C-H aromatic
stretch; aromatics also show bands in the regions 1600-1585 and 1500-1400 (C-C in-ring stretch),
and 900-675 (C-H out-of-plane). The wide band just to the left of the 3192 band indicates O-H stretch
(alcohols and phenols).
Show NMR answer
You're not expected to be able to tell all the aromatic Hs apart. In fact, there are several structures
that could match this pattern, as far as you can tell from the information on this site:
2 dari 2 5/22/2014 10:27 PM


Problem 18
Formula: C H
8 14
C H
8 14
1 dari 2 5/22/2014 10:28 PM

Look for any 2 of pi bonds or aliphatic rings.
Show IR answer
The bands at 3000-2850 indicate C-H alkane stretches. There really aren't many other bands in the
spectrum to indicate functional groups. The compound is an alkyne; we would expect to see a carbon-
carbon triple bond stretch at 2260-2100, however, this is a weak band at best and often does not
show up on IR.
Show NMR answer
The integral values for A, B, and C need to be multiplied by 2 to get a total of 14 protons in the
molecule. By convention, integral values on an NMR spectrum are reported as the lowest common
multiple.
2 dari 2 5/22/2014 10:28 PM


Problem 19
Formula: C H N
9 13
C H N
9 13
9 12
1 dari 2 5/22/2014 10:29 PM


Look for an aromatic ring.
Show IR answer
The bands at 3000-2850 indicate C-H alkane stretches. The band at 3028 indicates C-H aromatic
and 900-675 (C-H out-of-plane). The bands in the region 1250-1020 could be due to C-N stretch. The
weak, broad banc at about 3500 could be amine N-H stretch or it could be a slight contamination of
an impurity (water) in the sample.
Show NMR answer
2 dari 2 5/22/2014 10:29 PM


Problem 20
Formula: C H
9 10
C H
9 10
7 14
1 dari 2 5/22/2014 10:30 PM


Show IR answer
The bands at 3000-2850 indicate C-H alkane stretches. The band at 3060 indicates C-H aromatic
and 900-675 (C-H out-of-plane).
Show NMR answer
Again, the integral values need to be multiplied by two to give the right number of Hs.
Previous Problem Problems list
2 dari 2 5/22/2014 10:30 PM

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Table of characteristic proton NMR chemical shifts.

type of proton type of compound chemical shift range, ppm

frequency, cm–1 bond functional group

Organic Chemistry at CU Boulder

Show Unsaturation answer

1 dari 2 5/22/2014 10:10 PM

Show Structure answer

Show NMR answer

Problems list Next Problem

2 dari 2 5/22/2014 10:10 PM

Organic Chemistry at CU Boulder

Show Unsaturation answer

1 dari 2 5/22/2014 10:12 PM

Look for 1 pi bond or aliphatic ring.

Show Structure answer

Show NMR answer

Previous Problem Problems list Next Problem

2 dari 2 5/22/2014 10:12 PM

Organic Chemistry at CU Boulder

Show Unsaturation answer

1 dari 2 5/22/2014 10:13 PM

Show Structure answer

Show NMR answer

A and B do not couple because of A's ability to H-bond.

Previous Problem Problems list Next Problem

2 dari 2 5/22/2014 10:13 PM

Organic Chemistry at CU Boulder

Show Unsaturation answer

1 dari 2 5/22/2014 10:15 PM

Show Structure answer

Show NMR answer

Previous Problem Problems list Next Problem

2 dari 2 5/22/2014 10:15 PM

Organic Chemistry at CU Boulder

Show Unsaturation answer

1 dari 2 5/22/2014 10:15 PM

Show Structure answer

Show NMR answer

Previous Problem Problems list Next Problem

2 dari 2 5/22/2014 10:15 PM

Organic Chemistry at CU Boulder

Show Unsaturation answer

1 dari 2 5/22/2014 10:16 PM

Show Structure answer

Show NMR answer

Previous Problem Problems list Next Problem

2 dari 2 5/22/2014 10:16 PM

Organic Chemistry at CU Boulder

1 dari 2 5/22/2014 10:17 PM

Show Unsaturation answer

Show Structure answer

Show NMR answer

Previous Problem Problems list Next Problem

2 dari 2 5/22/2014 10:17 PM

Organic Chemistry at CU Boulder

1 dari 2 5/22/2014 10:17 PM

Show Unsaturation answer

Show Structure answer

Show NMR answer

Previous Problem Problems list Next Problem

2 dari 2 5/22/2014 10:17 PM

Organic Chemistry at CU Boulder

Show Unsaturation answer

1 dari 2 5/22/2014 10:39 PM