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INFRARED
SPECTROSCOPY

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REGION PROCESS
X-ray
UV/Visible
Infrared
Microwave
Radio Frequency (nmr)
Bond-breaking
Electronic
Vibrational
Rotational
Nuclear and
Electronic Spin

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Infrared Spectrometer

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Molecular vibrations

IR-Tutor available in CB 280 is great

Basicall! t"o t!pes

stretc#ing vibrations
bending vibrations

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IR T$T%R

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T!pical Infrared &bsorption
Regions

C-' stretc#ing region

&l(anes C-' sp
)
stretc# * )000 cm
-+

&l(enes C-' sp
2
stretc# , )000 cm
-+

&l(!nes C-' sp stretc# - ))00 cm

-+

C-' bending region
C'
2
bending - +./0 cm
-+

C'
)
bending 0as!m1 appears near t#e
same value
C'
)
bending 0s!m1 - +)80 cm
-+

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'e2ane
C'
)
C'
2
C'
2
C'
2
C'
2
C'
)
C-' stretc#
C'
2
bend
C'
)
bend

How do you think the infrared
spectrum of polyethylene would
differ from the spectrum of
hexane?????

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+/30 - +.30 cm
-+

T#e C4C is found at about +/30 cm

-+
5
Monomers "ould be e2pected to s#o" t#e
C4C bond6 but in pol!mers t#e double
bond "ill be absent6 unless t#ere is a
ben7ene ring5

T#e double bonds in a ben7ene ring are

found in t#e range of about +/00 to +.30
cm
-+

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+-'e2ene
C'
2
C' C'
2
C'
2
C'
2
C'
)
sp
2
C-'
sp
)
C-' stretc#
C4C
stretc#
out of plane
bendings 0oops1

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Toluene
C'
)
sp
2
C-'
sp
)
C-'
aromatic
C4C
aromatic oops

%-' stretc#ing region

%-' ))00 cm
-+
0alco#ol15 Common
pol!mers "it# %-'8 cellulose and 9:&

%-' ))00 cm
-+
0acid6 broad and ugl!15
;icarbo2!lic acids are monomers5 <#en
t#e carbo2!lic acid is pol!meri7ed "it# an
diol6 !ou get an pol!ester5

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C!clo#e2anol
%'
%-'
stretc#
bending
C-%
stretc#
sp
)
C-' stretc#

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Butanoic &cid
C'
)
C'
2
C'
2
C %'
%
%-' stretc# C4% stretc#

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2230 cm
-+

C= 2230 cm
-+

T#e onl! common pol!mers "it# t#is functional
group8 pol!acr!lonitrile and &BS

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9ropanenitrile
C'
)
C'
2
C =
sp
)
C-'
C=

=-' stretc#ing region

))00 - ).00 cm
-+
>='
2
9rimar! amines give a pair of pea(s5
?ou don@t see primar! amines in
pol!mers5

-=' Secondar! amines give a single pea(

T#e =-' in pol!amides and pol!uret#anes
s#o" a ver! prominent singlet pea(

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+-Butanamine
C'
)
C'
2
C'
2
C'
2
='
2
=-'
stretc#
doublet
sp
)
C-' stretc#
=-'
bend
C'
2
C'
)
bend

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)-Met#!lben7enamine
='
2
C'
)
=-'
stretc#
sp
2
A sp
)
C-'
=-' bend
&romatic
C4C

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N-Bt#!lben7enamine
=' C'
2
C'
)
=-'
stretc#
sp
2
A sp
)
C-'
&romatic C4C

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+CC0 - +/C0 cm
-+

T#is is t#e carbon!l region &ll bands are

ver! strong

T#e follo"ing pol!mers "ould be e2pected

to s#o" prominent C4% pea(s8

9ol!esters

&cr!lics

9ol!amides and pol!uret#anes

9ol! et#er (etone 09BBD1

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C4% Stretc#ing in monomers
and pol!mers
Functional Group Frequency (cm
-1
)
Ester

Ketone

Carboxylic acid

Amide
!"# to !$$

!# to %&$

!$

%'$


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2-Butanone
C'
)
C C'
2
C'
)
%
sp
)
C-'
stretc#
C4% stretc#

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.-Met#!l-2-pentanone
C-' * )0006 C4% E +C+3 cm
-+
C'
)
C' C'
2
C C'
)
% C'
)
C-' stretc#
C4% stretc#

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Bt#!l Butanoate
C
%
%
C'
2
C'
2
C'
)
C'
2
C'
)
sp
)
C-'
C4% stretc#
C-% stretc#

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Butanoic &cid
C'
)
C'
2
C'
2
C %'
%
%-' stretc# C4% stretc#

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9ropanamide
C
='
2
%
C'
2
C'
)
=-' stretc#
0pair1
=-' bend
sp
)
C-'
C4% and

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ConFugation of C4% "it# C4C

ConFugation of a carbon!l "it# a C4C

bond s#ifts values to lo"er freGuencies

Hor (etones and esters6 subtract about )0

cm
-+
for conFugation "it# C4%

ConFugated (etone 4 +/I0 to +/80 cm

-+

ConFugated ester 4 +C+0 to +C00 cm

-+

C4C becomes Guite strong

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.-Met#!l-)-penten-2-one
C C
C'
)
C'
)
C C'
)
%
'
C-' stretc#
C4%
stretc#
C4C
stretc#

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&cetop#enone
C C'
)
%
C-' stretc#
conF C4%
aromatic C4C

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C-J stretc#ing region

C-Cl C83 to 3.0 cm

-+
6 often #ard to find
amongst t#e fingerprint bands

C-Br and C-I appear outside t#e useful

range of infrared spectroscop!5

C-H can be found easil!6 but aren@t t#at

common - e2ception
pol!tetrafluoroet#!lene

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Carbon Tetrac#loride
C Cl Cl
Cl
Cl
no C-'
C-Cl stretc#