Use the technique LISTED BELOW to assign the peaks to the functional group vibrations LISTED BELOW. MOre than one peak $($label$)$ may appear for a "vibration" of a functional group.

$-$ Functional Group Vibration:

$-$ Aromatic C$-$H stretching Vibration:

$-$ Ketone C$=$O stretching Vibration:

$-$ Oop bending vibration on monosubtitued aromatic ring $($phenyl$)$

Methyl, Methylene, and Methine

$2990-2850-$CH$3$ and$-$CH$2-$ and CH $($s$)($sp$3$ C$-$H bonds$)$

$1475-1450$ Asymmetric bend and scissor

$1375$ Symmetric bend $($methyl group$)$

$1385-1370$ Gem$-$dimethyl doublet $($and tert$-$butyl$)($w$)$

$720$ Rocking, for chains $>4$ carbons

$743-734$ Propyl chain

$790-770$ Ethyl chain

Alkenes

$3080=$CH$2$ asymmetric stretch $($m to s$)($sp$2$ C$-$H bonds$)$

$3020=$CHR asymmetric stretch $($m to s$)($sp$2$C$-$H bonds$)$

$1645$ RCH$=$CH$2($w$)$

$1655$ R$2$C$=$CH$2($w$)$

$1660$ cis$-$RCH$=$CHR $($w$)$

$1675$ trans$-$RCH$=$CHR $($w$)$

$1670$ R$2$C$=$CHR and R$2$C$=$CR$2($w$)$

$990,900$ RHC$=$CH$2$ out of plane bending $($oop$)($s$)$

$900$ R$2$C$=$CH$2($oop$)($s$)$

$685$ cis$-$RCH$=$CHR $($oop$)($s$)$

$965$ trans$-$RCH$=$CHR $($oop$)($s$)$

Rings

$3103$ cyclopropane asymmetric stretch

$3024$ cyclopropane symmetric stretch

$3056-2990$ Epoxides

$1250$ epoxide symmetric ring stretch $($vs$)$

$950-890$ epoxide asymmetric stretching of ring

Alkynes

$3315-3270$CH $($s$,$ sharp$)$

$2260-2210$ C$$C internal

$2140-2100$ C$$C external

Nitriles

$2300-2200$ C$$N stretch $($s$,$ sharp$)$

Aromatic Hydrocarbons

$3100-3000$ C$-$H asymmetric stretch

$2000-1650$ benzene substitution pattern region

$770-730,710-690$ monosubstituted benzene $($oop$)($ m to s$)$

$770-735$ ortho substituted benzene $($oop$)($m to s$)$

$860-800$ para substituted benzene $($oop$)($m to s$)$

$780,880$ meta substituted benzene $($oop$)($m to s$)$

Carbonyls

$1900-1580$ Carbonyl

$1720-1700$ ketones $($vs$)$

$1740-1720$ aldehydes $($vs$)$

$2900-2700$ aldehyde CH $($w$,2$ peaks$)$

$-20$ to $30$ cm$-1$ for each C$=$C attached to carbonyl $($s$)$

$1625-$diketones

Carboxylic Acids

$2700-2500$ O$-$H dimer peak $($broad$)$

$1420$ coupled C$-$O stretch in COOH

$1300$ coupled C$-$O stretch in COOH

$935$ O$-$H $($oop$)$

$1760-1710$ C$=$O

Esters

$1750-1740$ Ester C$=$O

$1280-1000$ Ester CO

$1200$ methyl ester triplet

Anhydrides

$1820-1750$ C$=$O $($s two bands$)$

Ethers

$1190$ OCH$3$

$2830-2815$ methyl ether band

Alcohols

$3639-3633$ primary alcohols $($dilute$)$

$3625-3620$ secondary alcohols $($dilute$)$

$3619-3611$ tertiary alcohols $($dilute$)$

$3611-3603$ aromatic alcohols $($dilute$)$

$3500-3450$ alcohol dimers $($s$,$ broad$)$

$3400-3200$ alcohols polymers $($s$,$ broad$)$

$1140-1090$ secondary and tertiary alcohols

$1065-1015$ cyclic alcohols

$1060-1025$ primary alcohols

Amines

$3500-3300$ primary amines $($doublet$),$ secondary amines $($singlet$)($s$,$ broad$)$

$1650-1590$ N$-$H primary amine deformation

$1650-1510$ N$-$H secondary amine deformation

$1360-1250,1280-1180$ aromatic amines

$3000-2000$ ammonium band

$2820-2760$ N$-$methyl amines

Amides

$1715-1650$ amide carbonyl $($amide I band$)$

$1670-1640$ amide II band

Chlorides

$760-540$ CCl stretch