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91Ó°ÊÓ

For each of the following pairs of compounds, identify one IR absorption band that could be used to distinguish between them:

a.

b.

c.

d.

e.

f.cis-2-butene and trans-2-butene

g.

h.

i.

j.

k.

l.

Short Answer

Expert verified

a.An absorption band at 1250cm−1is present for the ester.

b.An absorption band at720cm−1 is present for the second compound.

c.An absorption band at 3650 to3200cm−1 is present for the first compound.

d.An absorption band at 3500 to3300cm−1 is present for the first compound.

e.The second compound has an absorption of 1385 to 1365cm−1.

f.The trans isomer has an absorption in the range of 980 to role="math" localid="1652421519275" 960cm−1. The cis isomer has an absorption around 730 to role="math" localid="1652421536620" 675cm−1.

g. The C=O absorption band possess a value of role="math" localid="1652421551920" 1740cm−1for the first compound. The ketone which is the second compound possess a wave number of role="math" localid="1652421559908" 1720cm−1.

h. The C=O absorption band comprise a larger wavenumber for role="math" localid="1652421619465" β,role="math" localid="1652421651997" γ-unsaturated ketone and the value is role="math" localid="1652421662734" 1720cm−1. The role="math" localid="1652421671530" α,βunsaturated ketone has a value ofrole="math" localid="1652421680991" 1680cm−1.

i. The alkene has an absorption band at 1680 to role="math" localid="1652421694246" 1600cm−1due to the C=C stretching vibration and at 3100 to role="math" localid="1652421704176" 3020cm−1due to anrole="math" localid="1652421712844" sp2 C-H stretching vibration. The alkyne has an absorption band at 2260 to2100cm−1 .

j.An absorption band at 2820 and 2720cm−1due to aldehyde C-H stretching vibration is present for the first compound.

k.An absorption band at1600cm−1 and1500cm−1 (aromatic ring stretching vibrations) and at 3100 to3020cm−1(sp2C-H) stretching vibration is present for the compound with benzene ring and absent for the compound with cyclohexane ring.

l. Absorption band at 990cm−1and 910cm−1due to an sp2C-H bending vibration that is present for terminal alkene.

Step by step solution

01

Step-by-step-solutionStep 1: IR spectroscopy

A significant amount of energy is needed to stretch a bond than to bend it. The absorption bands of stretching vibrations are observed in the functional group region (4000-1400)cm-1and those of the bending vibrations are observed in the fingerprint region(1400-600)cm-1 .

02

Identifying the IR absorption band to distinguish a pair of compounds

a. An absorption band at 1250cm−1due to C-O stretching vibration is present for the ester which is the first compound and absent for the ketone which is the second compound.

b. An absorption band at 720cm−1due to in-phase rocking of the five adjacent methylene groups would be present for the second compound, heptane and absent for the first compound, methylcyclohexane.

c. An absorption band at 3650 to role="math" localid="1652422159839" 3200cm−1is present due to the O-H stretching is present for the first molecule which is an alcohol and second molecule which is an ether.

d. An absorption band at 3500 to role="math" localid="1652422155668" 3300cm−1due to an N-H stretching vibration is present for the first compound which is an amide and absent for the second compound which is an ester.

e. The secondary alcohol which is the second compound has an absorption band at 1385 to role="math" localid="1652422209400" 1365cm−1for the methyl group. The primary alcohol which is the first compound does not have a methyl group and an absorption band.

f. The trans isomer has a C-H bending absorption at 980 to 960cm−1. The cis isomer has an absorption band at 730 to 675cm−1. In addition, a weak C=C absorption band at 1680 to 1600cm−1is present for cis isomer and absent for the trans isomer, as the trans isomer is symmetrical.

g. The C=O absorption band possess a larger wave number ,1740cm−1for the ester which is the first compound. The ketone which is the second compound possess a wave number of1720cm−1.

h. The C=O absorption band comprise a larger wavenumber for β,γ-unsaturated ketone and the value is 1720cm−1. The α,βunsaturated ketone has a value of 1680cm−1, as the double bonds of the latter are conjugated.

i. The alkene has an absorption band at 1680 to 1600cm−1due to the C=C stretching vibration and at 3100 to 3020cm−1due to an sp2C-H stretching vibration that is not present in the alkyne. The alkyne has an absorption band at 2260 to 2100cm−1that is not present in the alkene.

j. An absorption band at 2820 and 2720cm−1due to aldehyde C-H stretching vibration is present for the aldehyde which is the first compound, and the second compound which is a ketone would not exhibit this peak.

k. An absorption band at 1600cm−1and 1500cm−1(aromatic ring stretching vibrations) and at 3100 to 3020cm−1(sp2C-H)stretching vibration is present for the compound with benzene ring and absent for the compound with cyclohexane ring. An absorption band at 2960 to 2850cm−1due to sp3C-H stretching vibration is present for the compound with cyclohexane ring and absent for the compound with benzene ring.

l. Absorption band at 990cm−1and 910cm−1due to ansp2 C-H bending vibration that is present for terminal alkene and absent for internal alkene.

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